(4bS,5aS,8aS)-6,7,8,8a,9,10-hexahydro-5aH-phenanthro[4b,5-b]oxirene

Base Information

• Chemical Name: (4bS,5aS,8aS)-6,7,8,8a,9,10-hexahydro-5aH-phenanthro[4b,5-b]oxirene
• CAS No.: 121865-86-9
• Molecular Formula: C₁₄H₁₆O
• Molecular Weight: 200.28
• Mol file: 121865-86-9.mol

Synonyms:

Chemical Property of (4bS,5aS,8aS)-6,7,8,8a,9,10-hexahydro-5aH-phenanthro[4b,5-b]oxirene

Chemical Property:

• Vapor Pressure: 0.000456mmHg at 25°C
• Boiling Point: 324.7°Cat760mmHg
• Flash Point: 145.2°C
• Density: 1.16g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4bS,5aS,8aS)-6,7,8,8a,9,10-hexahydro-5aH-phenanthro[4b,5-b]oxirene

There total 14 articles about (4bS,5aS,8aS)-6,7,8,8a,9,10-hexahydro-5aH-phenanthro[4b,5-b]oxirene 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:

1,2,3,9,10,10a-hexahydrophenanthrene (62690-96-4) → (4β,4aβ,,10aα)-4,4a-epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (121865-86-9,121958-18-7) + (4α,4aα,,10aα)-4,4a-epoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (121865-86-9,121958-18-7)

Guidance literature:

With Perbenzoic acid; sodium hydrogencarbonate; In diethyl ether; at 0 ℃;

DOI:10.1021/jo00277a034

Reference yield:

1,2,3,9,10,10a-hexahydrophenanthrene (62690-96-4) → (4β,4aβ,,10aα)-4,4a-epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (121865-86-9,121958-18-7) + (4α,4aα,,10aα)-4,4a-epoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (121865-86-9,121958-18-7)

Guidance literature:

With Perbenzoic acid; sodium hydrogencarbonate; In diethyl ether; at 0 ℃;

DOI:10.1021/jo00277a034

Reference yield:

2-ethoxycarbonyl-1-tetralone (6742-26-3) → (4β,4aβ,,10aα)-4,4a-epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (121865-86-9,121958-18-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) MeONa / 1.) MeOH, room temp., 90 min, 2a.) MeOH, 18 h, 2b.) reflux, 3 h

2: 89 percent / 48percent aq. HBr/HBr(gas) / propionic acid / 4 h / Heating

3: 12.6 g / 2 h / 110 °C

4: 1.) BuLi / tetrahydrofuran / 1.) RT, 1 h, 2.) reflux, 5 h

5: 0.46 g / N-bromoacetamide / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

6: 0.26 g / t-BuOK / benzene / 1 h / Ambient temperature

With n-butyllithium; potassium tert-butylate; hydrogen bromide; sodium methylate; N-bromoacetamide; In tetrahydrofuran; water; propionic acid; benzene;

DOI:10.1021/jo00277a034

upstream raw materials:

1,2,3,9,10,10a-hexahydrophenanthrene

(4α,4aβ,10aα)-t-4-bromo-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthren-r-4a-ol

2-ethoxycarbonyl-1-tetralone

2-(4-bromobutyl)-1-tetralone