(4abeta,9alpha,10alpha)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene

Base Information

• Chemical Name: (4abeta,9alpha,10alpha)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene
• CAS No.: 28352-34-3
• Molecular Formula: C₁₄H₁₆O
• Molecular Weight: 200.28
• DSSTox Substance ID: DTXSID70951035
• Mol file: 28352-34-3.mol

Synonyms:(4abeta,9alpha,10alpha)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene;(4abeta,9beta,10beta)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene;28352-32-1;28352-34-3;CCRIS 7424;CCRIS 7427;syn-trans-9,10-Epoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthrene;anti-trans-9,10-Epoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthrene;Phenanthrene, 9,10-epoxy-1,2,3,4,4a,9,10,10a-octahydro-, anti-trans-;Phenanthrene, 9,10-epoxy-1,2,3,4,4a,9,10,10a-octahydro-, syn-trans-;DTXSID70951035;1a,1b,2,3,4,5,5a,9b-Octahydrophenanthro[9,10-b]oxirene

Chemical Property of (4abeta,9alpha,10alpha)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene

Chemical Property:

• Vapor Pressure: 0.000411mmHg at 25°C
• Boiling Point: 326.4°Cat760mmHg
• Flash Point: 146.1°C
• PSA: 12.53000
• Density: 1.124g/cm³
• LogP: 3.41390
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 200.120115130
• Heavy Atom Count: 15
• Complexity: 262

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)C3C(O3)C4=CC=CC=C24
• Isomeric SMILES: C1CCC2C(C1)[C@H]3[C@@H](O3)C4=CC=CC=C24

Technology Process of (4abeta,9alpha,10alpha)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene

There total 10 articles about (4abeta,9alpha,10alpha)-9,10-Epoxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 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: 96.5%

9(a)-Hydroxy-10(a)-brom-1,2,3,4,4a,9,10-(trans-4a,10a)-octahydrophenanthren (28352-33-2) → syn-9.10-Epoxy-1.2.3.4.4a.9.10.10a-(trans-4a.10a)-octahydrophenanthren (28352-34-3)

Guidance literature:

With Amberlite IRA-400 resin (hydroxyde form); for 7h; Ambient temperature;

DOI:10.1021/ja00371a029

Reference yield:

8,9-trans-hexahydrophenanthrene (16804-85-6) → syn-9.10-Epoxy-1.2.3.4.4a.9.10.10a-(trans-4a.10a)-octahydrophenanthren (28352-34-3) + (1aR,1bR,5aR,9bS)-1a,1b,2,3,4,5,5a,9b-Octahydro-1-oxa-cyclopropa[l]phenanthrene (28352-32-1)

Guidance literature:

With sodium hydroxide; N-Bromosuccinimide; water; Multistep reaction; 1.) DMSO, r.t., 1 h, 2.) toluene, r.t., 2.5 h;

DOI:10.1021/jo00087a042

Reference yield:

(RS)-2-phenylcyclohexanone (1444-65-1) → syn-9.10-Epoxy-1.2.3.4.4a.9.10.10a-(trans-4a.10a)-octahydrophenanthren (28352-34-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Br₂, 2.) 2,6-lutidine

2: 1.) NaOEt, 2.) TsOH, ethyl orthoformate, 3.) KOH

3: Zn/HCl

4: H₂SO₄

5: NaBH₄ / methanol

6: 100 percent / TsOH / benzene / 0.5 h / Heating

7: 71 percent / N-bromoacetamide / tetrahydrofuran; H₂O / 18 h / Ambient temperature

8: 96.5 percent / Amberlite IRA-400 resin (hydroxyde form) / 7 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; Amberlite IRA-400 resin (hydroxyde form); sulfuric acid; bromine; sodium ethanolate; toluene-4-sulfonic acid; orthoformic acid triethyl ester; zinc; N-bromoacetamide; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1021/ja00371a029

upstream raw materials:

9(a)-Hydroxy-10(a)-brom-1,2,3,4,4a,9,10-(trans-4a,10a)-octahydrophenanthren

8,9-trans-hexahydrophenanthrene

(RS)-2-phenylcyclohexanone

5,6-dihydro-[1,1'-biphenyl]-2(1H)-one

Downstream raw materials:

(+/-)-trans-4b,6,7,8,8a,10-hexahydro-5H-phenanthren-9-one

(4aR,9S,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol

(4aR,9R,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol