(1R^*,4S^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone

Base Information

• Chemical Name: (1R^*,4S^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone
• CAS No.: 117711-28-1
• Molecular Formula: C₁₇H₁₉BrO₂
• Molecular Weight: 335.241
• Mol file: 117711-28-1.mol

Synonyms:(1R^*,4S^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone

Chemical Property of (1R^*,4S^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R^*,4S^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone

There total 2 articles about (1R^*,4S^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone 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:

(4R*,4aR*,8aS*)-4-hydroxy-3-methoxy-4,4a,5,8-tetrahydro-1(8aH)-naphthalenone (40702-41-8,113458-00-7,117711-08-7) → (1R*,4S*,4aS*,6S*,7S*,8aR*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone (117711-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-bromosuccinimide / tetrahydrofuran / 1 h / 25 °C

2: 2.) p-toluenesulfonic acid / 1.) THF, diethyl ether, 0 deg C, 0.5 h, 2.) CH₂Cl₂, 25 deg C, 0.5 h

3: 1.) CuI / 1.) ether, cyclohexane, diethyl ether, 0 deg C, 10 min, 2.) THF, -40 deg C, 0.5 h

With N-Bromosuccinimide; copper(l) iodide; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1021/jo00260a017

Reference yield:

(1R*,4aS*,6S*,7S*,8aR*)-6-bromo-1,7-epoxy-4a,5,6,7,8,8a-hexahydro-4-methyl-2(1H)-naphthalenone (113458-02-9,117773-57-6) + phenyllithium (591-51-5) → (1R*,4S*,4aS*,6S*,7S*,8aR*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone (117711-28-1)

Guidance literature:

With copper(l) iodide; Yield given. Multistep reaction; 1.) ether, cyclohexane, diethyl ether, 0 deg C, 10 min, 2.) THF, -40 deg C, 0.5 h;

DOI:10.1021/jo00260a017

Reference yield: 50.0%

(E)-2-penten-1-ol (1576-96-1) + (1R*,4S*,4aS*,6S*,7S*,8aR*)-6-bromo-1,7-epoxy-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-4-phenyl-2(1H)-naphthalenone (117711-28-1) → (1R*,4R*,4aS*,6S*,7S*,8aR*)-6-bromo-1,7-epoxy-4-methyl-1,4,4a,5,6,7,8,8a-octahydro-2-(1-oxahex-3(E)-enyl)-4-phenylnaphthalene (117711-31-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 4h; Heating;

DOI:10.1021/jo00260a017

upstream raw materials:

(1R^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4a,5,6,7,8,8a-hexahydro-4-methyl-2(1H)-naphthalenone

phenyllithium

(4R^*,4aR^*,8aS^*)-4-hydroxy-3-methoxy-4,4a,5,8-tetrahydro-1(8aH)-naphthalenone

Downstream raw materials:

(1R^*,4R^*,4aS^*,6S^*,7S^*,8aR^*)-6-bromo-1,7-epoxy-4-methyl-1,4,4a,5,6,7,8,8a-octahydro-2-(1-oxahex-3(E)-enyl)-4-phenylnaphthalene

(1R^*,4R^*,4aS^*,7S^*,8aR^*)-1,7-epoxy-1,4,4a,7,8,8a-hexahydro-4-methyl-2-(1-oxahex-3(E)-enyl)-4-phenylnaphthalene

(1R^*,1'S^*,3S^*,4R^*,4aS^*,7s^*,8aR^*)-1,7-epoxy-3-(1'-ethylprop-2'-enyl)-3,4,4a,7,8,8a-hexahydro-4-methyl-4-phenyl-2(1H)-naphthalenone

(1R^*,1'S^*,4S^*,4aS^*,7S^*,8aR^*)-1,7-epoxy-3-(1'-ethylprop-3'-enyl)-1,4,4a,7,8,8a-hexahydro-2-hydroxy-4-methyl-4-phenylnaphthalene