(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

Base Information

• Chemical Name: (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
• CAS No.: 110143-12-9
• Molecular Formula: C₂₂H₂₆O₂
• Molecular Weight: 322.447
• Mol file: 110143-12-9.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 99.0%

(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 (110143-11-8,110221-10-8,117773-60-1,117773-61-2) → (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 (110143-12-9,117773-62-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; for 1h;

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) → (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 (110143-12-9,117773-62-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 50 percent / p-toluenesulfonic acid / benzene / 4 h / Heating

3: 86 percent / 1,8-diazobicyclo<5.4.0>undec-7-ene (DBU) / 3 h / 115 °C

4: 86 percent / N,N-dimethylaniline / dodecane / 4 h / 210 °C

5: 99 percent / sodium methoxide / methanol; tetrahydrofuran / 1 h

With copper(l) iodide; sodium methylate; toluene-4-sulfonic acid; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dodecane; benzene;

DOI:10.1021/jo00260a017

Reference yield:

(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 (113493-29-1,117773-59-8) → (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 (110143-12-9,117773-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / N,N-dimethylaniline / dodecane / 4 h / 210 °C

2: 99 percent / sodium methoxide / methanol; tetrahydrofuran / 1 h

With sodium methylate; N,N-dimethyl-aniline; In tetrahydrofuran; methanol; dodecane;

DOI:10.1021/jo00260a017

upstream raw materials:

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

(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

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