3,4-Epoxy-3,4-dihydrophenanthrene

Base Information

• Chemical Name: 3,4-Epoxy-3,4-dihydrophenanthrene
• CAS No.: 39834-45-2
• Molecular Formula: C₁₄H₁₀O
• Molecular Weight: 194.233
• DSSTox Substance ID: DTXSID20960399
• Wikidata: Q27109896
• Mol file: 39834-45-2.mol

Synonyms:39834-45-2;Phenanthrene-3,4-oxide;3,4-epoxy-3,4-dihydrophenanthrene;14-oxatetracyclo[8.5.0.02,7.013,15]pentadeca-1(10),2,4,6,8,11-hexaene;1a,9c-dihydrophenanthro[3,4-b]oxirene;Phenanthro(3,4-b)oxirene, 1a,9c-dihydro-;Phenanthro[3,4-b]oxirene, 1a,9c-dihydro-;CHEBI:25955;DTXSID20960399;3,4-Epoxy-3,4-dihydro-phenanthrene;FT-0673669;Q27109896

Chemical Property of 3,4-Epoxy-3,4-dihydrophenanthrene

Chemical Property:

• Vapor Pressure: 1.51E-05mmHg at 25°C
• Boiling Point: 377°Cat760mmHg
• Flash Point: 174.6°C
• PSA: 12.53000
• Density: 1.265g/cm³
• LogP: 3.30650
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 194.073164938
• Heavy Atom Count: 15
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

Phenanthrene 3,4-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4C(O4)C=C3
• Uses: An initial mammalian metabolite of Phenanthrene.

Technology Process of 3,4-Epoxy-3,4-dihydrophenanthrene

There total 27 articles about 3,4-Epoxy-3,4-dihydrophenanthrene 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: 60.0%

(-)-(3S,4S)-1-Bromo-3-acetoxy-4-chloro-1,2,3,4-tetrahydrophenanthrene (354762-78-0) → (3R/S,4S/R)-3,4-Epoxy-3,4-dihydrophenanthrene (89772-86-1,39834-45-2)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 0 ℃; for 12h;

DOI:10.1039/b009712h

Reference yield:

phenanthrene (85-01-8) → phenanthrene-9,10-oxide (585-08-0,84489-06-5) + (3R/S,4S/R)-3,4-Epoxy-3,4-dihydrophenanthrene (89772-86-1,39834-45-2) + 1,2-phenanthrene oxide (39834-44-1) + 1-phenanthrenol (2433-56-9) + 4-phenanthrol (7651-86-7) + 9-Phenanthrol (484-17-3)

Guidance literature:

With Pyrazin-N-Oxid(PyzNO); In dichloromethane; Irradiation; the similar arene oxide formation (t.l.c. evidence) for acenaphthene;

Reference yield:

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1,3-dibromo-1,2,3,4-tetrahydro-phenanthren-4-yl ester → (+)-(3S,4R)-3,4-epoxy-3,4-dihydrophenanthrene (39834-45-2,66239-76-7,89772-86-1)

Guidance literature:

With sodium methylate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)81884-0

upstream raw materials:

phenanthrene

(-)-(3S,4S)-1-Bromo-3-acetoxy-4-chloro-1,2,3,4-tetrahydrophenanthrene

3,4-Dihydrophenanthrene

(+/-)-cis-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene

Downstream raw materials:

phenanthrene 3,4-oxide

Refernces

• 1、 Balani, Suresh K.,Boyd, Derek R.,Cassidy, E. Sally,Devine, Gregory I.,Malone, John F.,et al.. "A General Method for the Resolution of Cyclic trans-Bromohydrin Enantiomers. Absolute Configuration by Crystal Structure Analysis of a 2-Methoxy-2-phenyl-2-trifluoromethylacetate (MTPA) Diastereoisomer". . p. 2751 - 2756. Retrieved 2007/10/02.
• 2、 Balani, Suresh K.,Boyd, Derek R.,Cassidy, E. Sally,Greene, Ruth M. E.,McCombe, Kenneth M.,et. al.. "AN IMPROVED METHOD FOR THE SYNTHESIS OF OPTICALLY PURE EPOXIDE AND ALCOHOL DERIVATIVES OF CHIRAL BROMOHYDRINS". . p. 3277 - 3280. Retrieved 2007/10/02.