(1R,2S)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

Base Information

Chemical Name:(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid
CAS No.:139025-41-5
Molecular Formula:C₁₅H₁₄O₅
Molecular Weight:274.273
Hs Code.:

Synonyms:(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

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Chemical Property of (1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

Chemical Property:

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Technology Process of (1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

There total 1 articles about (1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: 17680-04-5
(3,4-methylenedioxy)phenylmagnesium bromide

: 935-79-5
cis-1,2,3,6-tetrahydrophthalic anhydride

: 139025-41-5
(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

Guidance literature:: In tetrahydrofuran;
DOI:10.1016/0040-4039(91)85045-7

Reference yield:

: 139025-41-5
(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

: 139025-48-2
(3R*,4aR*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2-oxo-8,9-(methylenedioxy)-Δ^1(11a)-5,11-methanomorphanthridine

Guidance literature:: Multi-step reaction with 18 steps

1: 1) Et₃N, ethyl chloroformate, 2) NaN₃ / 1) acetone, ice-cooling, 0.5 h, 2) acetone, water, ice-cooling, 1 h

2: 16 h / Heating

3: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CHCl₃ / 1 h / Ambient temperature

5: 100 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane / 2 h / Ambient temperature

6: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature

7: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h

8: 1) BH₃*THF, 2) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min

9: 100 percent / pyridine / 1 h / Ambient temperature

10: 80.6 percent / methanesulfonic acid, Ac₂O / 1,2-dichloro-ethane / 2 h / Ambient temperature

11: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature

12: 82.5 percent / p-TsOH*H₂O / CHCl₃ / 1.33 h / Ambient temperature

13: 90.7 percent / sodium bis(2-methoxyethoxy)aluminum hydride / o-xylene / 0.58 h / Heating

14: 74.6 percent / diisobutylaluminum hydride / toluene / 2 h / Ambient temperature

15: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / ice-cooling

16: 33 percent / DBU / o-xylene / 2.5 h / Ambient temperature

17: 1) PhSeCl, 2) NaIO₄ / 1) MeOH, 15-20 deg C, sonication, 2 h, 2) H₂O, 10 min

18: 31.2 percent / bis(tetrabutylammonium) dichromate / CHCl₃ / 3 h / Heating

With pyridine; sodium hydroxide; sodium periodate; sodium azide; Phenylselenyl chloride; borane-THF; tetra(n-butyl)ammonium dichromate(VI); methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; chloroformic acid ethyl ester; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; dmap; osmium(VIII) oxide; In 1,4-dioxane; methanol; dichloromethane; chloroform; o-xylene; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00052a051

Reference yield:

: 139025-41-5
(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

: 144609-85-8
(3R*,4aR*,11R*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2,2-dimethoxy-Δ^1(11a)-8,9-(methylenedioxy)-5,11-methanomorphanthridine

Guidance literature:: Multi-step reaction with 19 steps

1: 1) Et₃N, ethyl chloroformate, 2) NaN₃ / 1) acetone, ice-cooling, 0.5 h, 2) acetone, water, ice-cooling, 1 h

2: 16 h / Heating

3: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CHCl₃ / 1 h / Ambient temperature

5: 100 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane / 2 h / Ambient temperature

6: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature

7: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h

8: 1) BH₃*THF, 2) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min

9: 100 percent / pyridine / 1 h / Ambient temperature

10: 80.6 percent / methanesulfonic acid, Ac₂O / 1,2-dichloro-ethane / 2 h / Ambient temperature

11: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature

12: 82.5 percent / p-TsOH*H₂O / CHCl₃ / 1.33 h / Ambient temperature

13: 90.7 percent / sodium bis(2-methoxyethoxy)aluminum hydride / o-xylene / 0.58 h / Heating

14: 74.6 percent / diisobutylaluminum hydride / toluene / 2 h / Ambient temperature

15: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / ice-cooling

16: 33 percent / DBU / o-xylene / 2.5 h / Ambient temperature

17: 1) PhSeCl, 2) NaIO₄ / 1) MeOH, 15-20 deg C, sonication, 2 h, 2) H₂O, 10 min

18: 31.2 percent / bis(tetrabutylammonium) dichromate / CHCl₃ / 3 h / Heating

19: 99.1 percent / p-TsOH*H₂O / methanol / 2 h / Ambient temperature

With pyridine; sodium hydroxide; sodium periodate; sodium azide; Phenylselenyl chloride; borane-THF; tetra(n-butyl)ammonium dichromate(VI); methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; chloroformic acid ethyl ester; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; dmap; osmium(VIII) oxide; In 1,4-dioxane; methanol; dichloromethane; chloroform; o-xylene; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00052a051