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14 reactions in Reaxys
2017-11-11 21h:16m:06s (EST)
O
1. Query HO OH
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O
O
HO
HO OH
O
Rx-ID: 290814 View in Reaxys 1/14 Yield
Conditions & References With alkaline aqueous H2O2 Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118 View in Reaxys 1.2 : Stage 2 - preparation of5-Hydroxy-eugenol (L)i) Stage 2 - preparation of5-Hydroxy-eugenol (L)i)To a solution of eugenol-5-aldehyde (2.5 g) in pyridine (16 cc) was added one normal aqueous sodium hydroxide (19.5 cc) and the clear yellow solution treated dropwise with 6percent hydrogen peroxide (9.6 cc) with vigorous shaking. The colour changed to red and when the solution developed turbidity a little more water was added in order toremove it. After leaving at the room temperature for 1.5 hours with occasional shaking, the solution was acidified with hydrochloric acid while cooling. The hydroxy compound separated as a heavy liquid; this separation was completed by adding common salt and the mixture was extracted thrice with ether. The ether extract was washed successively with hydrochloric acid, aqueous sodium bicarbonate and a smallquantity of water. After drying over sodium sulphate it was evaporated to remove the solvent completely; a pale brown viscous oil was left behind (2.0 g). The product fromthree experiments was collected and distilled under reduced pressure (20 mm); the main fraction distilled at 176°. 5-hydroxy eugenol was a colourless viscous liquid. It was soluble in 5percent aqueous sodium hydroxide and 10percent aqueous sodium carbonate to give a deep brown solution. With a drop of ferric chloride in alcoholic solution it gave adeep violet colour changing to brownish violet and brown with another drop. After standing for a few minutes the colour changed to a stable olive green. It gave a yellow precipitate with lead acetate. With pyridine, dihydrogen peroxide, sodium hydroxide in water, Time= 1.5h, T= 20 °C Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English View in Reaxys OH
HO
O
O
HO O
OH
O
Rx-ID: 37043035 View in Reaxys 2/14 Yield
Conditions & References General procedure: LtAPS1 and LtPPS1: In vitro standard enzymatic assays were carried out in 100 mM MES–KOH (pH 7.0 and 6.5, respectively) as described above for LtCAAT1, but with monolignol acetates (21–25, 0.5 mM) as substrates and NADPH (0.5 mM) as cofactor. (0019) Optimum pH for enzymatic reactions (LtCAAT1/LtAPS1/ LtPPS1) was determined using the following buffer systems (100 mM): citrate, pH 3.35–6.85; MES–KOH, pH 5.5– 7.0; potassium phosphate, pH 6.0–8.0; Tris–HCl, pH 7.0–9.0; Bis-Tris propane, pH 6.5–9.0; all at 0.5 pH unit intervals, with assays carried out at 30 °C. (0020) Initial velocity kinetics were determined by assaying: LtCAAT1 under standard conditions in citrate buffer (100 mM, pH 4.8) with 18 different monolignol (16–20) concentrations (3.33–500 μM); LtAPS1 in MES–KOH (100 mM, pH 7.0) with 18 different monolignol acetate (21–25) concentrations (3.33 μM– 3.3 mM); and LtPPS1 in MES–KOH (100 mM, pH 6.5) with 14 different monolignol acetate (21–25) concentrations (3.33 μM–1 mM). Assays were performed in quadruplicate, with controls in the absence of acetyl-CoA/NADPH. With propenylphenol synthase from Larrea tridentata, Reduced nicotinamide-adenine dinucleotide in aq. buffer, T= 30 °C , pH= 6.5, Kinetics Kim, Sung-Jin; Vassao, Daniel G.; Moinuddin, Syed G.A.; Bedgar, Diana L.; Davin, Laurence B.; Lewis, Norman G.; Archives of Biochemistry and Biophysics; vol. 541; nb. 1; (2014); p. 37 - 46 View in Reaxys
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O
O
OH
HO
OH
OH
Rx-ID: 13382799 View in Reaxys 3/14 Yield
Conditions & References Reaction Steps: 2 1: 98 percent / K2CO3 With potassium carbonate, 2: Claisen rearrangement Jing, Xiao-Bi; Wang, Li; Han, Ying; Shi, Yao-Cheng; Liu, Yong-Hong; Sun, Jing; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 1001 - 1004 View in Reaxys Reaction Steps: 2 1: 72 percent / K2CO3 / acetone / Heating 2: 78 percent / 240 - 250 °C With potassium carbonate in acetone, 2: Claisen and Cope rearrangements Mamouni; Soukri; Lazar; Akssira; Guillaumet; Tetrahedron Letters; vol. 45; nb. 12; (2004); p. 2631 - 2633 View in Reaxys Reaction Steps: 2 1.1: NaOH / acetone / 0.5 h 1.2: 98 percent / acetone / 6 h / 20 °C 2.1: 100 percent / 336000 h / 150 °C With sodium hydroxide in acetone, 2.1: Claisen rearrangement Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63 View in Reaxys Reaction Steps: 2 1.1: NaOH / acetone / 0.5 h 1.2: acetone / 6 h / 20 °C 2.1: 168000 h / 150 °C With sodium hydroxide in acetone, 2.1: Claisen rearrangement Jing, Xiaobi; Gu, Wenxin; Bie, Pingyan; Ren, Xinfeng; Pan, Xinfu; Synthetic Communications; vol. 31; nb. 6; (2001); p. 861 - 867 View in Reaxys
OH HO
OH
HO O HO
O O
O OH
O
O
OH
O
O HO
HO
OH
OH
OH
Rx-ID: 2804378 View in Reaxys 4/14 Yield
Conditions & References With hydrogenchloride in 1,4-dioxane, water, Time= 2h, T= 75 °C Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442 View in Reaxys Reaction Steps: 2 1: 1percent H2SO4 / 3 h / 70 °C 2: 2percent HCl / dioxane; H2O / 2 h / 75 °C
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With hydrogenchloride, sulfuric acid in 1,4-dioxane, water Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442 View in Reaxys
HO O HO
OH O
O OH
HO
O
O
O
HO
OH
OH
OH
Rx-ID: 2803160 View in Reaxys 5/14 Yield
Conditions & References With hydrogenchloride in 1,4-dioxane, water, Time= 2h, T= 75 °C Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442 View in Reaxys
OH HO
O O
HO
O
OH OH
O
O
O HO
HO
OH
OH OH
Rx-ID: 2803195 View in Reaxys 6/14 Yield
Conditions & References With hydrogenchloride in 1,4-dioxane, water, Time= 2h, T= 75 °C Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442 View in Reaxys
O O
HO
O
HO OH
Rx-ID: 342789 View in Reaxys 7/14 Yield 100 %
Conditions & References Time= 336000h, T= 150 °C , Claisen rearrangement Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63 View in Reaxys
78 %
T= 240 - 250 °C , Claisen and Cope rearrangements Mamouni; Soukri; Lazar; Akssira; Guillaumet; Tetrahedron Letters; vol. 45; nb. 12; (2004); p. 2631 - 2633 View in Reaxys T= 170 - 200 °C , unter Wasserstoff Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437 View in Reaxys Surrey; Journal of the American Chemical Society; vol. 70; (1948); p. 2887,2889 View in Reaxys
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T= 200 °C , Erhitzen unter Wasserstoff Trikojus; White; Nature (London, United Kingdom); vol. 144; (1939); p. 1016; Journal of the Chemical Society; (1949); p. 436 View in Reaxys Time= 168000h, T= 150 °C , Claisen rearrangement Jing, Xiaobi; Gu, Wenxin; Bie, Pingyan; Ren, Xinfeng; Pan, Xinfu; Synthetic Communications; vol. 31; nb. 6; (2001); p. 861 - 867 View in Reaxys Claisen rearrangement Jing, Xiao-Bi; Wang, Li; Han, Ying; Shi, Yao-Cheng; Liu, Yong-Hong; Sun, Jing; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 1001 - 1004 View in Reaxys
HO
O
O
HO OH
Rx-ID: 4301029 View in Reaxys 8/14 Yield
Conditions & References (i) (KO3S)2NO, aq. KH2PO4, acetone, (ii) aq. Na2S2O4, Et2O, Multistep reaction Dallacker,F.; Sluysmans,R.; Monatshefte fuer Chemie; vol. 100; (1969); p. 560 - 566 View in Reaxys Reaction Steps: 2 2: alkaline aqueous H2O2 With alkaline aqueous H2O2 Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118 View in Reaxys Reaction Steps: 2 1: 1-Hexylamine / 6 h / |Heating 2: dihydrogen peroxide; pyridine; sodium hydroxide / water / 1.5 h / 20 °C With pyridine, 1-Hexylamine, dihydrogen peroxide, sodium hydroxide in water Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English View in Reaxys
O HO
OH
KHCO3 HO
OH
OH
Rx-ID: 15334502 View in Reaxys 9/14 Yield
Conditions & References Reaction Steps: 3 1.1: aq. Na2B4O7 / ethanol / 0.5 h 1.2: 85 percent / K2CO3 2.1: NaOH / acetone / 0.5 h 2.2: 98 percent / acetone / 6 h / 20 °C 3.1: 100 percent / 336000 h / 150 °C With borax, sodium hydroxide in ethanol, acetone, 3.1: Claisen rearrangement Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63 View in Reaxys
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Reaction Steps: 3 1.1: Na2B4O7*10H2O / ethanol; H2O / 0.5 h 1.2: 3.8 g / K2CO3 / H2O; ethanol 2.1: NaOH / acetone / 0.5 h 2.2: acetone / 6 h / 20 °C 3.1: 168000 h / 150 °C With borax, sodium hydroxide in ethanol, water, acetone, 3.1: Claisen rearrangement Jing, Xiaobi; Gu, Wenxin; Bie, Pingyan; Ren, Xinfeng; Pan, Xinfu; Synthetic Communications; vol. 31; nb. 6; (2001); p. 861 - 867 View in Reaxys
HO O HO O HO
O
O
OH
HO
O
O HO
HO
OH
OH
Rx-ID: 25991394 View in Reaxys 10/14 Yield
Conditions & References With hydrogenchloride, Time= 2h, T= 100 °C Hussein; Hashim; El-Sharawy; Seliem; Linscheid; Lindequist; Nawwar; Phytochemistry; vol. 68; nb. 10; (2007); p. 1464 - 1470 View in Reaxys
O OH HO OH
O
HO OH
Rx-ID: 37043026 View in Reaxys 11/14 Yield
Conditions & References Reaction Steps: 2 1: Larrea tridentata cinnamyl alcohol acyltransferase-1 / aq. buffer / 0.5 h / 30 °C / pH 7.9 / |Enzymatic reaction 2: Reduced nicotinamide-adenine dinucleotide; propenylphenol synthase from Larrea tridentata / aq. buffer / 30 °C / pH 6.5 With Larrea tridentata cinnamyl alcohol acyltransferase-1, propenylphenol synthase from Larrea tridentata, Reduced nicotinamide-adenine dinucleotide in aq. buffer Kim, Sung-Jin; Vassao, Daniel G.; Moinuddin, Syed G.A.; Bedgar, Diana L.; Davin, Laurence B.; Lewis, Norman G.; Archives of Biochemistry and Biophysics; vol. 541; nb. 1; (2014); p. 37 - 46 View in Reaxys
O
O
O
HO
OH
OH
Rx-ID: 343313 View in Reaxys 12/14 Yield
Conditions & References T= 170 - 200 °C , unter Wasserstoff Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437 View in Reaxys Surrey; Journal of the American Chemical Society; vol. 70; (1948); p. 2887,2889 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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T= 190 °C , Erhitzen unter Wasserstoff Trikojus; White; Nature (London, United Kingdom); vol. 144; (1939); p. 1016; Journal of the Chemical Society; (1949); p. 436 View in Reaxys
O HO
aqueous NaIO3
OH
HO
OH
OH
Rx-ID: 13398883 View in Reaxys 13/14 Yield
Conditions & References Reaction Steps: 3 1: 85 percent / Na2B4O7*10H2O; K2CO3 2: 98 percent / K2CO3 With borax, potassium carbonate, 3: Claisen rearrangement Jing, Xiao-Bi; Wang, Li; Han, Ying; Shi, Yao-Cheng; Liu, Yong-Hong; Sun, Jing; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 1001 - 1004 View in Reaxys
O
HO OH
Rx-ID: 7395374 View in Reaxys 14/14 Yield
Conditions & References Kuwatsuka; Casida; Journal of Agricultural and Food Chemistry; vol. 13; (1965); p. 528,529,530 View in Reaxys
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