trans-1,2,3,4,4a,10a-Hexahydrophenanthrene

Base Information

• Chemical Name: trans-1,2,3,4,4a,10a-Hexahydrophenanthrene
• CAS No.: 16804-85-6
• Molecular Formula: C₁₄H₁₆
• Molecular Weight: 184.281
• DSSTox Substance ID: DTXSID30937431
• Mol file: 16804-85-6.mol

Synonyms:trans-1,2,3,4,4a,10a-Hexahydrophenanthrene;1,2,3,4,4a,10a-hexahydrophenanthrene;16804-85-6;1,2,3,4,4aalpha,10abeta-Hexahydrophenanthrene;CCRIS 7433;Phenanthrene, 1,2,3,4,4aalpha,10abeta-hexahydro-;ET3ZV4PX3X;UNII-ET3ZV4PX3X;DTXSID30937431

Chemical Property of trans-1,2,3,4,4a,10a-Hexahydrophenanthrene

Chemical Property:

• Vapor Pressure: 0.00135mmHg at 25°C
• Boiling Point: 307°Cat760mmHg
• Flash Point: 131.4°C
• Density: 1.015g/cm³
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 184.125200510
• Heavy Atom Count: 14
• Complexity: 228

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)C=CC3=CC=CC=C23

Technology Process of trans-1,2,3,4,4a,10a-Hexahydrophenanthrene

There total 19 articles about trans-1,2,3,4,4a,10a-Hexahydrophenanthrene 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: 100.0%

trans-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-ol (25662-65-1) → 8,9-trans-hexahydrophenanthrene (16804-85-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.5h; Heating;

DOI:10.1021/ja00371a029

Reference yield: 87.0%

8,9-trans-6-<2-(dimethylamino)-1(R)-phenylethoxy>octahydrophenanthrene (84694-53-1,84694-54-2) → 8,9-trans-hexahydrophenanthrene (16804-85-6)

Guidance literature:

With potassium hydrogensulfate; In perchloric acid; benzene; for 3h; Heating;

DOI:10.1021/ja00344a028

Reference yield:

trans-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone (21656-46-2) → 8,9-trans-hexahydrophenanthrene (16804-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol

2: 100 percent / TsOH / benzene / 0.5 h / Heating

With sodium tetrahydroborate; toluene-4-sulfonic acid; In methanol; benzene;

DOI:10.1021/ja00371a029

upstream raw materials:

1,2,3,4,4a,9,10,10a-Octahydro-phenanthrol-⁽⁹⁾

cis-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one

cyclohexene

1-cyclohexenyl(phenyl)methanone

Downstream raw materials:

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

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

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

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

Refernces

• 1、 Nelson,W.L.,Miller,D.D.. "-". . p. 807 - 814. Retrieved 1970.
• 2、 Sayer, J. M.,Yagi, H.,Silverton, J. V.,Friedman, S. L.,Whalen, D. L.,Jerina, D. M.. "Conformational Effects in the Hydrolyses of Rigid Benzylic Epoxides: Implications for Diol Epoxides of Polycyclic Hydrocarbons". . p. 1972 - 1978. Retrieved 2007/10/02.