77546-81-7

Basic information

• Product Name: 20-aminopregna-1,4-dien-3-one
• Synonyms: 20-aminopregna-1,4-dien-3-one
• CAS NO: 77546-81-7
• Molecular Formula: C₂₁H₃₁NO
• Molecular Weight: 313.47694
• EINECS: 278-720-1
• Mol File: 77546-81-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 445.8°C at 760 mmHg
• Flash Point: 223.4°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 3.84E-08mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 20-aminopregna-1,4-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 20-aminopregna-1,4-dien-3-one(77546-81-7)
• EPA Substance Registry System: 20-aminopregna-1,4-dien-3-one(77546-81-7)

Safety Data

• Hazardous Substances Data: 77546-81-7(Hazardous Substances Data)

Usage

Chemical Classification

Synthetic steroid compound

Class

Aminosteroid

Derivative of

Pregna-1,4-diene-3,20-dione

Functional Group

Amino group at the 20th position

Application

Medicinal chemistry and drug development

Potential

Steroid nature
Amino group for biological activities and interactions

Pharmacological Effects

Potential pharmacological effects

Utility

Precursor for synthesis of other pharmaceutical agents

Research Needs

Further research required for exploring full potential and applications in pharmaceutical industry

InChI:InChI=1/C21H31NO/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h8,10,12-13,16-19H,4-7,9,11,22H2,1-3H3/t13?,16-,17+,18-,19-,20-,21+/m0/s1

Upstream product

• 1162-54-5 pregna-1,4-diene-3,20-dione 

Downstream Products

• 134332-55-1 20-succinamylpregna-1,4-dien-3-one 

Relevant articles and documents

Regioselective reactions of 1,2-dehydroprogesterone: Syntheses of pregnane derivatives as possible contragestational agents

A few pregnane derivatives were synthesized from 1,2-dehydroprogesterone (1). Ring A of 1,2-dehydroprogesterone was aromatized without affecting C-20, and the resulting acetoxy compound (2) after hydrolysis yielded 1-hydroxy-4-methyl-19-norpregna-1,3,5(10)-trien-20-one (3). Reactions of the phenol (3) with alkyl halides yielded the ethers 6a-6b and 7. Opening of the oxirane ring in 7 with secondary amines furnished the aminoalcohols 8a-8b. Friedelcraft's reaction of 3 with maleic anhydride and chloracetyl chloride led to the formation of 9 and 10, respectively. Base-catalyzed ring closure of 10 yielded 1-acetyl- 12a-methyl-8-oxo-5[H]-1,2,3,3a,3b, 4,8,9,10b, 11,12, 12a-dodecahydrocyclopenta (7,8)phenanthro (3,4-b) furan (11), which reacted with aromatic aldehydes regioselectively to furnish 12a-12b. Reaction of 1 with triethylorthoformate in the presence of boron trifluoride etherate involved the participation of C-21, and the carbonyl at C-3 remained unaffected. The product 13 was identified as 21-[2-hydroxyvinyl]-21-norpregna-1,4-diene-3,20-dione. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate did not attack ring A and smoothly furnished the amine 14 which, on reaction with succinic anhydride, gave20-succinamylpregna-1,4-dien-3-one (15).