1-Dehydroprogesterone

Base Information

• Chemical Name: 1-Dehydroprogesterone
• CAS No.: 1162-54-5
• Molecular Formula: C21H28 O2
• Molecular Weight: 312.452
• NSC Number: 63538
• UNII: 257V0W056G
• DSSTox Substance ID: DTXSID50921958
• Nikkaji Number: J662.264J
• Wikidata: Q27115793
• Metabolomics Workbench ID: 35426
• ChEMBL ID: CHEMBL479717
• Mol file: 1162-54-5.mol

Synonyms:1,2-dehydroprogesterone;1-dehydroprogesterone;1-dehydroprogesterone, (13alpha,17alpha)-(+-)-isomer

Chemical Property of 1-Dehydroprogesterone

Chemical Property:

• Vapor Pressure: 2.91E-08mmHg at 25°C
• Melting Point: 151-152 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 449.2°Cat760mmHg
• Flash Point: 167.4°C
• PSA: 34.14000
• Density: 1.1g/cm³
• LogP: 4.49950
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 312.208930132
• Heavy Atom Count: 23
• Complexity: 628

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2-Dehydroprogesterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)C=CC34C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)C
• Uses: 1,2-Dehydroprogesterone is a progesterone impurity which displays anti-flu virus effects. Also used int he preparation of cytotoxic agents with steroidal derivatives.

Technology Process of 1-Dehydroprogesterone

There total 39 articles about 1-Dehydroprogesterone 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%

(20S)-3-oxopregna-1,4-diene-20-carboxaldehyde (81201-82-3) → pregna-1,4-diene-3,20-dione (1162-54-5)

Guidance literature:

With [2,2]bipyridinyl; ruthenium trichloride; air; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 15h; Ambient temperature;

Reference yield: 89.6%

20-methyl-3-oxopregna-1,4-dien-21-al (96790-16-8) → pregna-1,4-diene-3,20-dione (1162-54-5)

Guidance literature:

With [2,2]bipyridinyl; copper diacetate; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1246/bcsj.58.1081

Reference yield: 86.0%

22-hydroxy-23,24-bis-norchola-1,4-diene-3-one (35525-27-0) → pregna-1,4-diene-3,20-dione (1162-54-5) + (20S)-3-oxopregna-1,4-diene-20-carboxaldehyde (81201-82-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.25h;

upstream raw materials:

Progesterone

20β_F-hydroxy-pregna-1,4-dien-3-one

(20R)-pregn-5-ene-3β,20-diol

3β-hydroxy-pregn-4-en-20-one

Downstream raw materials:

(+/-)-progesterone

21E-(4-methylbenzylidene)pregn-1,4-diene-3,20-dione

21E-(2-nitrobenzylidene)pregn-1,4-diene-3,20-dione

21E-(4-methoxybenzylidene)pregn-1,4-diene-3,20-dione

Refernces

• 1、 Vischer et al.. "-". . p. 835,838. Retrieved 1955.
• 2、 Fan, Ning-Juan,Tang, Jiang-Jiang,Li, He,Li, Xiao-Jun,Luo, Bo,Gao, Jin-Ming. "Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives". . p. 182 - 190. Retrieved 2013.
• 3、 Fan, Ning-Juan,Han, Yang-Yang,Li, Yuan-Feng,Gao, Jin-Ming,Tang, Jiang-Jiang. "Synthesis of novel 4′-acylamino modified 21E-benzylidene steroidal derivatives and their cytotoxic activities". . p. 20 - 26. Retrieved 2017.
• 4、 McCarry et al.. "". . p. 4416,4417. Retrieved 1973.
• 5、 -. "ENABLING CHOLESTEROL CATABOLISM IN HUMAN CELLS". Paragraph 0029; 0039; 0041; 0054; 0060. . Retrieved 2020/07/05.
• 6、 -. "PROCESS FOR PREPARATION OF DYDROGESTERONE". Paragraph 0079; 0088. . Retrieved 2018/09/08.