10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one

Base Information

• Chemical Name: 10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
• CAS No.: 4075-07-4
• Molecular Formula: C19H26O
• Molecular Weight: 270.415
• NSC Number: 93234
• ChEMBL ID: CHEMBL141998
• Mol file: 4075-07-4.mol

Synonyms:CHEMBL141998;NSC-93234;NSC93234;NCIOpen2_005884;SCHEMBL20424563;BDBM50422490;FT-0662144

Chemical Property of 10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one

Chemical Property:

• Vapor Pressure: 2.69E-06mmHg at 25°C
• Melting Point: 131.5-133.5 °C
• Refractive Index: 1.559
• Boiling Point: 390.3 °C at 760mmHg
• Flash Point: 179.2 °C
• PSA: 17.07000
• Density: 1.07 g/cm³
• LogP: 4.68440
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 270.198365449
• Heavy Atom Count: 20
• Complexity: 514

Purity/Quality:

99%, ^*data from raw suppliers

4,16-Androstadien-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC=C2)CCC4=CC(=O)CCC34C
• Uses: Androstadienone is a prominent androstene present on male human axillary hair and on the male axillary skin surface. Studies suggest that Androstadienone has a strong pheromone-like activities in hum ans. Androstadienone is a metabolite of Testosterone (T155000).

Technology Process of 10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one

There total 27 articles about 10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one 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: 90.0%

17β-methoxycarbonyloxy-androst-4-en-3-one (19865-18-0) → 4,16-androstadien-3-one (4075-07-4)

Guidance literature:

In toluene; at 460 ℃;

DOI:10.1002/hlca.19830660121

Reference yield: 78.0%

(8R,9S,10R,13S,14S)-17-bromo-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one → 4,16-androstadien-3-one (4075-07-4)

Guidance literature:

With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; [CoCl₂(dmgH)2(pyridine)]; potassium carbonate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/jacs.1c06768

Reference yield: 76.0%

Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (182243-71-6) → 4,16-androstadien-3-one (4075-07-4) + 3-oxoandrost-4-en-17α-yl acetate (1425-09-8)

Guidance literature:

With 18-crown-6 ether; cesium acetate; In benzene; for 72h; Heating;

DOI:10.1016/0040-4039(96)01333-0

upstream raw materials:

3-oxoandrost-4-en-17α-yl benzoate

HAD

testosterone

17β-methoxycarbonyloxy-androst-4-en-3-one

Downstream raw materials:

5α-androstan-5-ol

4-androsten-3-one

Androstene oxide

Refernces

• 1、 Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Lukashev, Nikolay V.,Beletskaya, Irina P.. "Alkynylation of steroids via Pd-free Sonogashira coupling". . p. 5542 - 5555. Retrieved 2015/05/20.
• 2、 Nahar, Lutfun,Turner, Alan B.,Sarker, Satyajit D.. "Convenient synthesis of monomeric steroids from steroidal oxalate dimers using flash vacuum pyrolysis (FVP)". experimental part. p. 359 - 366. Retrieved 2010/11/03.