1,2,3,4,4A,9,10,10A-Octahydrophenanthrene-9,10-diol

Base Information

• Chemical Name: 1,2,3,4,4A,9,10,10A-Octahydrophenanthrene-9,10-diol
• CAS No.: 53446-96-1
• Molecular Formula: C₁₄H₁₈O₂
• Molecular Weight: 218.296
• DSSTox Substance ID: DTXSID90509653,DTXSID20877579
• Mol file: 53446-96-1.mol

Synonyms:646068-56-6;1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE-9,10-DIOL;SCHEMBL14577672;DTXSID20877579;DTXSID90509653;9,10-PHENANTHRENEDIOL, 1,2,3,4,4A,9,10,10A-OCTAH;53446-96-1

Chemical Property of 1,2,3,4,4A,9,10,10A-Octahydrophenanthrene-9,10-diol

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 218.130679813
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC2C(C1)C(C(C3=CC=CC=C23)O)O

Technology Process of 1,2,3,4,4A,9,10,10A-Octahydrophenanthrene-9,10-diol

There total 14 articles about 1,2,3,4,4A,9,10,10A-Octahydrophenanthrene-9,10-diol 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:

syn-9.10-Epoxy-1.2.3.4.4a.9.10.10a-(trans-4a.10a)-octahydrophenanthren (28352-34-3) → (+/-)-trans-4b,6,7,8,8a,10-hexahydro-5H-phenanthren-9-one (19634-95-8,19634-96-9) + (4aR,9S,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol (53446-99-4,646068-56-6) + (4aR,9R,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol (53446-96-1,646068-56-6)

Guidance literature:

In 1,4-dioxane; water; pH > 7;

DOI:10.1021/ja00371a029

Reference yield:

(RS)-2-phenylcyclohexanone (1444-65-1) → (4aR,9R,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol (53446-96-1,646068-56-6)

Guidance literature:

Multi-step reaction with 9 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

9: HClO₄ / dioxane; H₂O

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; perchloric acid; Amberlite IRA-400 resin (hydroxyde form); sulfuric acid; bromine; sodium ethanolate; toluene-4-sulfonic acid; orthoformic acid triethyl ester; zinc; N-bromoacetamide; In tetrahydrofuran; 1,4-dioxane; methanol; water; benzene;

DOI:10.1021/ja00371a029

Reference yield:

5,6-dihydro-[1,1'-biphenyl]-2(1H)-one (36702-38-2) → (4aR,9R,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol (53446-96-1,646068-56-6)

Guidance literature:

Multi-step reaction with 8 steps

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

2: Zn/HCl

3: H₂SO₄

4: NaBH₄ / methanol

5: 100 percent / TsOH / benzene / 0.5 h / Heating

6: 71 percent / N-bromoacetamide / tetrahydrofuran; H₂O / 18 h / Ambient temperature

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

8: HClO₄ / dioxane; H₂O

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; perchloric acid; Amberlite IRA-400 resin (hydroxyde form); sulfuric acid; sodium ethanolate; toluene-4-sulfonic acid; orthoformic acid triethyl ester; zinc; N-bromoacetamide; In tetrahydrofuran; 1,4-dioxane; methanol; water; benzene;

DOI:10.1021/ja00371a029

upstream raw materials:

syn-9.10-Epoxy-1.2.3.4.4a.9.10.10a-(trans-4a.10a)-octahydrophenanthren

(RS)-2-phenylcyclohexanone

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

<(1S*,2R*)-3-oxo-2-phenylcyclohexyl>acetic acid