(5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one

Base Information

• Chemical Name: (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one
• CAS No.: 1173-00-8
• Molecular Formula: C₂₇H₂₆O
• Molecular Weight: 366.503

Synonyms:(5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one

Chemical Property of (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one

Chemical Property:

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Technology Process of (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one

There total 3 articles about (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one 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: 74.0%

(5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,10,10a,11-hexahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one (87598-38-7) → (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one (1173-00-8)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; In diethylene glycol; 1.) 120 deg C, 3 h, 2.) 210 deg C, 7 h;

DOI:10.1021/ja00363a020

Reference yield:

Cycloheptene (628-92-2,45509-99-7) + 1,3-diphenylisobenzofuran (5471-63-6) → (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one (1173-00-8)

Guidance literature:

Cycloheptene; With benzoic acid methyl ester; In dichloromethane; at -78 ℃; for 1h; UV-irradiation;

1,3-diphenylisobenzofuran; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja991315l

Reference yield:

(8R)- and (8S-)(5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-ol (87598-37-6,87678-16-8) → (5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one (1173-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

2: 74 percent / KOH, N₂H₄*H₂O / bis-(2-hydroxy-ethyl) ether / 1.) 120 deg C, 3 h, 2.) 210 deg C, 7 h

With potassium hydroxide; hydrazine hydrate; pyridinium chlorochromate; In dichloromethane; diethylene glycol;

DOI:10.1021/ja00363a020

upstream raw materials:

(5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,10,10a,11-hexahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-one

Cycloheptene

1,3-diphenylisobenzofuran

(8R)- and (8S-)(5α,5aα,10aβ,11α)-5,11-epoxy-5a,6,7,8,9,10,10a,11-octahydro-5,11-diphenyl-5H-cycloheptanaphthalen-8-ol

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