Reaxys
PubChem
eMolecules
Reactions (155)
Substances (1)
Citations (87)
Structure
Structure/Compound Data Chemical Name: 4-cyclohexyl-butan-2-one Reaxys Registry Number: 1209723
CAS Registry Number: 103-78-6 Type of Substance: isocyclic Molecular Formula: C9H16O Linear Structure Formula: C6H11CH2COCH3
Molecular Weight: 140.225 InChI Key: UHBZEAPZATVYKV-UHFFFAOYSA-N
1
N° of preparations All Preps | All Reactions
Available Data
N° of ref.
58 prep out of 155 reactions.
Identification Physical Data (32) Spectra (26)
87
Synthesize | Hide Details Find similar Chemical Names and Synonyms 4-cyclohexyl-butan-2-one Identification Substance Label (27) Label
Reference
1r
Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong
Organic Letters, 2016 , vol. 18, # 2 p. 228 - 231 Title/Abstract Full Text View citing articles Show Details
19c
Annadi, Krishna; Wee, Andrew G. H.
Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1021 - 1038 Title/Abstract Full Text View citing articles Show Details
2a
Martin,S.F.; Chou,T.
Tetrahedron Letters, 1978 , p. 1943 - 1946 Full Text View citing articles Show Details
Castelbou, Jessica Llop; Bres-Femenia, Emma; Blondeau, Pascal; Chaudret, Bruno; Castilln, Sergio; Claver, Carmen; Godard, Cyril
ChemCatChem, 2014 , vol. 6, # 11 p. 3160 - 3168 Title/Abstract Full Text View citing articles Show Details
1h
Roiban, Gheorghe-Doru; Agudo, Ruben; Reetz, Manfred T.
Angewandte Chemie - International Edition, 2014 , vol. 53, # 33 p. 8659 - 8663 Title/Abstract Full Text View citing articles Show Details
4d, byprod.
Tosaki, Shin-Ya; Hara, Keiichi; Gnanadesikan, Vijay; Morimoto, Hiroyuki; Harada, Shinji; Sugita, Mari; Yamagiwa, Noriyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu
Journal of the American Chemical Society, 2006 , vol. 128, # 36 p. 11776 - 11777 Title/Abstract Full Text View citing articles Show Details
3f
Saito, Shinichi; Dobashi, Naotomo; Wakatsuki, Yasuo
Chemistry Letters, 2005 , vol. 34, # 4 p. 504 - 505 Title/Abstract Full Text View citing articles Show Details
7
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
Tab. 2
Kogan, Vladimir; Aizenshtat, Zeev; Neumann, Ronny
New Journal of Chemistry, 2002 , vol. 26, # 3 p. 272 - 274 Title/Abstract Full Text View citing articles Show Details
39c
Kuroda; Takamura; Tenda; Itani; Tomishima; Akahane; Sakane
Chemical and Pharmaceutical Bulletin, 2001 , vol. 49, # 8 p. 988 - 998 Title/Abstract Full Text View citing articles Show Details
2, R1 = cyclohexyl
Hayes; Shipman; Twin
Chemical Communications, 2000 , # 18 p. 1791 - 1792 Title/Abstract Full Text View citing articles Show Details
4b
Linker, Ursula; Kersten, Berthold; Linker, Torsten
Tetrahedron, 1995 , vol. 51, # 36 p. 9917 - 9926 Title/Abstract Full Text View citing articles Show Details
18 (R=cyclohexyl; R'=H)
Maruoka; Concepcion; Yamamoto
Synthesis, 1994 , # SPEC. ISS. p. 1283 - 1290 Title/Abstract Full Text View citing articles Show Details
5c
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details
9b
Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z.
Tetrahedron, 1985 , vol. 41, # 23 p. 5507 - 5516 Title/Abstract Full Text View citing articles Show Details
TAB. 2. Entry 1. Col 2.
Jaouhari, Rabih; Filliatre, Claude; Villenave, Jean-Jacques
Canadian Journal of Chemistry, 1983 , vol. 61, p. 2295 - 2298 Title/Abstract Full Text Show Details
6, R=cyclohexyl, R'=Me
Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.
Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details
1, run 15
Citterio, Attilio; Ferrario, Francesco; Bernardinis, Silvia De
Journal of Chemical Research, Miniprint, 1983 , # 12 p. 2669 - 2683 Title/Abstract Full Text Show Details
3a
Jaouhari, Rabih; Maillard, Bernard; Filliatre, Claude; Villenave, Jean-Jacques
Synthesis, 1982 , # 9 p. 760 - 763 Title/Abstract Full Text Show Details
4
Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.
Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details
Keton
Audier et al.
Bulletin de la Societe Chimique de France, 1978 , vol. <II>, p. 585 Full Text Show Details
Label
Reference
3
Tamao,K. et al.
Chemistry Letters, 1976 , p. 1239 - 1242 Full Text View citing articles Show Details
9
Hajek; Malek
Synthesis, 1976 , p. 315 Full Text Show Details
16
Agosta,W.C. et al.
Journal of Organic Chemistry, 1976 , vol. 41, p. 136 - 141 Full Text View citing articles Show Details
6
Brown,H.C.; Gupta,S.K.
Journal of the American Chemical Society, 1975 , vol. 97, p. 5249 - 5255 Full Text View citing articles Show Details
VI
Nagao et al.
Kogyo Kagaku Zasshi, 1969 , vol. 72, p. 236 Chem.Abstr., 1969 , vol. 70, # 114372 Full Text Show Details
VII
Andreew et al.
Biol. Akt. Soedin., 1968 , p. 79,84 Chem.Abstr., 1970 , vol. 72, # 3076 Full Text Show Details
III
Barltrop,J.A.; Thomson,A.
Journal of the Chemical Society [Section] C: Organic, 1968 , p. 155 - 166 Full Text View citing articles Show Details
Patent-Specific Data (1) Location in Patent
Reference
Claim
Southern Illinois University Foundation
Patent: US3953494 A1, 1976 ; Title/Abstract Full Text Show Details
Derivative (4) Comment (Derivative)
Reference
2,4-DNP-Derivat: F:117-118grad
Schultz
Journal of Organic Chemistry, 1971 , vol. 36, p. 383 Full Text View citing articles Show Details
2.4-Dinitrophenylhydrazon: F: 114-119grad (EtOH)
Andreew et al.
Biol. Akt. Soedin., 1968 , p. 79,84 Chem.Abstr., 1970 , vol. 72, # 3076 Full Text Show Details
2,4-Dinitro-phenylhydrazon C15H20N4O4: F: 119-120grad (abs. A.)
Stodola et al.
Biochemical Journal, 1964 , vol. 93, p. 92,96 Full Text Show Details
as 2,4-dinitro-phenylhydrazone (mp: 114-115 degree )
Jacquier et al.
Bulletin de la Societe Chimique de France, 1956 , p. 1653,1664 Full Text Show Details
Physical Data Boiling Point (18) Boiling Point
Pressure (Boiling Point)
Comment (Boiling Point)
Reference
48 - 50 °C
1.1 Torr
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details
35 °C
0.1 Torr
Citterio, Attilio; Ferrario, Francesco; Bernardinis, Silvia De
Journal of Chemical Research, Miniprint, 1983 , # 12 p. 2669 - 2683 Title/Abstract Full Text Show Details
65 - 68 °C
4 Torr
Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.
Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details
88 - 89 °C
20 Torr
Jaouhari, Rabih; Maillard, Bernard; Filliatre, Claude; Villenave, Jean-Jacques
Synthesis, 1982 , # 9 p. 760 - 763 Title/Abstract Full Text Show Details
Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.
Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details
85 - 86 °C
16 Torr
Carenini; Carissimi; Gentili; Grumelli; Picciola; Ravenna
Arzneimittel-Forschung/Drug Research, 1976 , vol. 26, # 12 p. 2127 - 2136 Title/Abstract Full Text View citing articles Show Details
30 °C
0.1 Torr
Hegedus,L.S.; Stiverson,R.K.
Journal of the American Chemical Society, 1974 , vol. 96, p. 3250 - 3254 Full Text View citing articles Show Details
91 °C
22 Torr
Nagao et al.
Kogyo Kagaku Zasshi, 1969 , vol. 72, p. 236 Chem.Abstr., 1969 , vol. 70, # 114372 Full Text Show Details
70 - 72 °C
10 Torr
Andreew et al.
Biol. Akt. Soedin., 1968 , p. 79,84 Chem.Abstr., 1970 , vol. 72, # 3076 Full Text Show Details
196 - 199 °C
755 Torr
Stodola et al.
Biochemical Journal, 1964 , vol. 93, p. 92,96 Full Text Show Details
87 - 88 °C
19 Torr
Bailey; Daly
Journal of Organic Chemistry, 1957 , vol. 22, p. 1189,1192 Full Text Show Details
196 - 198 °C
Chiang
Journal of the Chinese Chemical Society (Peking), 1951 , vol. 18, p. 65,69, 74 Full Text Show Details
200.5 °C
Ipatieff; Haensel
Journal of Organic Chemistry, 1942 , vol. 7, p. 189,196 Full Text Show Details
194 - 195 °C
Guerbet
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1917 , vol. 164, p. 953 Bulletin de la Societe Chimique de France, 1918 , vol. <4> 23, p. 72 Full Text Show Details
761 Torr
Wallach
Justus Liebigs Annalen der Chemie, 1912 , vol. 394, p. 372 Chem. Zentralbl., 1908 , vol. 79, # I p. 637,639 Full Text View citing articles Show Details
200 °C
83 - 85 °C
195 - 196 °C
Darzens; Rost
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911 , vol. 153, p. 773 Full Text Show Details
13 Torr
fluessig.
Hell; Schaal
Chemische Berichte, 1909 , vol. 42, p. 2232 Full Text Show Details
198 - 200 °C
Wallach
Justus Liebigs Annalen der Chemie, 1907 , vol. 353, p. 302 Chem. Zentralbl., 1907 , vol. 78, # II p. 53 Full Text Show Details
197 °C
Freundler
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906 , vol. 142, p. 344 Bulletin de la Societe Chimique de France, 1906 , vol. <3> 35, p. 548 Full Text Show Details
Refractive Index (6) Refractive Index
Wavelength (Refractive Index)
Temperature (Refractive Index)
Reference
1.4575
589 nm
20 °C
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details
1.4274
589 nm
20 °C
Jaouhari, Rabih; Maillard, Bernard; Filliatre, Claude; Villenave, Jean-Jacques
Synthesis, 1982 , # 9 p. 760 - 763 Title/Abstract Full Text Show Details
Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.
Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details
1.4512
589 nm
20 °C
Monfort et al.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1970 , vol. 67, p. 748,749-753 Full Text Show Details
1.451
589 nm
20 °C
Andreew et al.
Biol. Akt. Soedin., 1968 , p. 79,84 Chem.Abstr., 1970 , vol. 72, # 3076 Full Text Show Details
1.4499
589 nm
5 °C
Bailey; Daly
Journal of Organic Chemistry, 1957 , vol. 22, p. 1189,1192 Full Text Show Details
1.4514
589 nm
20 °C
Wallach
Justus Liebigs Annalen der Chemie, 1912 , vol. 394, p. 372 Chem. Zentralbl., 1908 , vol. 79, # I p. 637,639 Full Text View citing articles Show Details
Density (3) Density
Reference Temperature
Measurement Temperature
Reference
0.9127 g·cm-3
4 °C
25 °C
Monfort et al.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1970 , vol. 67, p. 748,749-753 Full Text Show Details
0.935 g·cm-3
0 °C
Guerbet
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1917 , vol. 164, p. 953 Bulletin de la Societe Chimique de France, 1918 , vol. <4> 23, p. 72 Full Text Show Details
0.905 g·cm-3
20 °C
Wallach
Justus Liebigs Annalen der Chemie, 1912 , vol. 394, p. 372 Chem. Zentralbl., 1908 , vol. 79, # I p. 637,639 Full Text View citing articles Show Details
Chromatographic Data (2) Chromatographic data
Location
Reference
GC (Gas chromatography)
supporting information
Deuss, Peter J.; Scott, Martin; Tran, Fanny; Westwood, Nicholas J.; De Vries, Johannes G.; Barta, Katalin
Journal of the American Chemical Society, 2015 , vol. 137, # 23 p. 7456 - 7467 Title/Abstract Full Text View citing articles Show Details
GC (Gas chromatography)
Castelbou, Jessica Llop; Bres-Femenia, Emma; Blondeau, Pascal; Chaudret, Bruno; Castilln, Sergio; Claver, Carmen; Godard, Cyril
ChemCatChem, 2014 , vol. 6, # 11 p. 3160 - 3168 Title/Abstract Full Text View citing articles Show Details
Crystal Property Description (2) Colour & Other Properties
Reference
colourless
Annadi, Krishna; Wee, Andrew G. H.
Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1021 - 1038 Title/Abstract Full Text View citing articles Show Details
yellow
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
Liquid/Vapour Systems (MCS) (1) Description (Liquid/Vapour Systems (MCS))
Reference
Activity coefficients of the components in the mixture
Monfort et al.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1970 , vol. 67, p. 748,749-753 Full Text Show Details
Spectra NMR Spectroscopy (15) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Coupling Nuclei
Solvents (NMR Spectroscopy)
Temperature (NMR Spectroscopy)
Frequency (NMR Spectroscopy)
Location
Comment (NMR Spectroscopy)
Reference
Chemical shifts Spectrum
1H
chloroform-d1
300 MHz
supporting information
Annadi, Krishna; Wee, Andrew G. H.
Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1021 - 1038 Title/Abstract Full Text View citing articles Show Details
Chemical shifts Spectrum
13C
chloroform-d1
75 MHz
supporting information
Annadi, Krishna; Wee, Andrew G. H.
Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1021 - 1038 Title/Abstract Full Text View citing articles Show Details
Chemical shifts Spectrum
1H
chloroform-d1
24.14 °C
400 MHz
supporting information
Genna, Douglas T.; Posner, Gary H.
Organic Letters, 2011 , vol. 13, # 19 p. 5358 5361 Title/Abstract Full Text View citing articles Show Details
Chemical shifts Spectrum
13C
chloroform-d1
27.24 °C
100 MHz
supporting information
Genna, Douglas T.; Posner, Gary H.
Organic Letters, 2011 , vol. 13, # 19 p. 5358 5361 Title/Abstract Full Text View citing articles Show Details
Spectrum
1H
Spectrum
13C
Chemical shifts
1H
Chemical shifts
13C
1H
Chemical shifts
13C
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
75.469 MHz
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
CDCl3
300 MHz
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
CDCl3
75 MHz
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
CDCl3
300 MHz
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
19.84 °C
1H
CDCl3
Jaouhari, R.; Filliatre, C.; Maillard, B.;
Villenave, J.J.
Tetrahedron, 1982 , vol. 38, # 21 p. 3137 3142 Title/Abstract Full Text View citing articles Show Details
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G. Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details
Linker, Ursula; Kersten, Berthold; Linker, Torsten
Tetrahedron, 1995 , vol. 51, # 36 p. 9917 9926 Title/Abstract Full Text View citing articles Show Details
Chemical shifts
1H
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G.
CDCl3
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details
Linker, Ursula; Kersten, Berthold; Linker, Torsten
Tetrahedron, 1995 , vol. 51, # 36 p. 9917 9926 Title/Abstract Full Text View citing articles Show Details
Spin-spin coupling constants
Chemical shifts
CDCl3
1H-1H
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G. Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details
Linker, Ursula; Kersten, Berthold; Linker, Torsten
Tetrahedron, 1995 , vol. 51, # 36 p. 9917 9926 Title/Abstract Full Text View citing articles Show Details
1H
Spin-spin coupling constants
NMR
IR Spectroscopy (8)
Jaouhari, Rabih; Maillard, Bernard; Filliatre, Claude; Villenave, Jean-Jacques
Synthesis, 1982 , # 9 p. 760 - 763 Title/Abstract Full Text Show Details
Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.
Tetrahedron, 1982 , vol. 38, # 21 p. 3137 3142 Title/Abstract Full Text View citing articles Show Details
Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z.
Tetrahedron, 1985 , vol. 41, # 23 p. 5507 5516 Title/Abstract Full Text View citing articles Show Details
Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.
Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details
CCl4
CCl4
1H-1H
Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z.
Tetrahedron, 1985 , vol. 41, # 23 p. 5507 5516 Title/Abstract Full Text View citing articles Show Details
Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.
Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details
Schultz
Journal of Organic Chemistry, 1971 , vol. 36, p. 383 Full Text View citing articles Show Details
Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Bands
neat liquid
Bands
Location
Comment (IR Spectroscopy)
Reference Annadi, Krishna; Wee, Andrew G. H.
Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1021 1038 Title/Abstract Full Text View citing articles Show Details
supporting information
neat (no solvent)
Genna, Douglas T.; Posner, Gary H.
Organic Letters, 2011 , vol. 13, # 19 p. 5358 - 5361 Title/Abstract Full Text View citing articles Show Details
Hayes, Jerome F.; Shipman, Michael; Twin, Heather
Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details
Bands
film
Bands
neat (no solvent)
1716 cm**(-1)
Linker, Ursula; Kersten, Berthold; Linker, Torsten
Tetrahedron, 1995 , vol. 51, # 36 p. 9917 - 9926 Title/Abstract Full Text View citing articles Show Details
Bands
neat (no solvent)
1712 cm**(-1)
Brown, Herbert C.; Imai, Toshiro; Bhat, N. G.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 5282 Title/Abstract Full Text View citing articles Show Details
Bands
neat (no solvent)
1710 cm**(-1)
Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z.
Tetrahedron, 1985 , vol. 41, # 23 p. 5507 - 5516 Title/Abstract Full Text View citing articles Show Details
Bands
neat (no solvent)
2950 - 840 cm**(-1)
Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.
Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details
Schultz
Journal of Organic Chemistry, 1971 , vol. 36, p. 383 Full Text View citing articles Show Details
IR
Mass Spectrometry (3) Description (Mass Spectrometry)
Location
Reference
HRMS (High resolution mass spectrometry) ESI (Electrospray ionisation) FAB (Fast atom bombardment) Spectrum
supporting information
Genna, Douglas T.; Posner, Gary H.
Organic Letters, 2011 , vol. 13, # 19 p. 5358 - 5361 Title/Abstract Full Text View citing articles Show Details
Audier et al.
Bulletin de la Societe Chimique de France, 1978 , vol. <II>, p. 585 Full Text Show Details
spectrum
Agosta,W.C. et al.
Journal of Organic Chemistry, 1976 , vol. 41, p. 136 - 141 Full Text View citing articles Show Details