19888-27-8

Basic information

• Product Name: (1R,6β)-7β-[(E)-5-Hydroxy-4-methyl-3-pentenyl]-7-methylbicyclo[4.1.0]hept-2-ene-3-methanol
• Synonyms: (1R,6β)-7β-[(E)-5-Hydroxy-4-methyl-3-pentenyl]-7-methylbicyclo[4.1.0]hept-2-ene-3-methanol;Sirenin;Sirenin【Allomyces】
• CAS NO: 19888-27-8
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.35
• Mol File: 19888-27-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 367.5°C at 760 mmHg
• Flash Point: 169.2°C
• Appearance: /
• Density: 1.036g/cm³
• Vapor Pressure: 6.81E-07mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: (1R,6β)-7β-[(E)-5-Hydroxy-4-methyl-3-pentenyl]-7-methylbicyclo[4.1.0]hept-2-ene-3-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,6β)-7β-[(E)-5-Hydroxy-4-methyl-3-pentenyl]-7-methylbicyclo[4.1.0]hept-2-ene-3-methanol(19888-27-8)
• EPA Substance Registry System: (1R,6β)-7β-[(E)-5-Hydroxy-4-methyl-3-pentenyl]-7-methylbicyclo[4.1.0]hept-2-ene-3-methanol(19888-27-8)

Safety Data

• Hazardous Substances Data: 19888-27-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H24O2/c1-11(9-16)4-3-7-15(2)13-6-5-12(10-17)8-14(13)15/h4,8,13-14,16-17H,3,5-7,9-10H2,1-2H3/b11-4+/t13-,14+,15+/m0/s1

Upstream product

• 121946-82-5 C₂₉H₂₈N₄O₁₂ 
• 173143-87-8 (1R,6S,7R)-7-Methyl-7-((E)-4-methyl-5-oxo-pent-3-enyl)-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester 
• 16933-56-5 (6E)-7,11-dimethyldodeca-6,10-dien-2-yn-1-ol 
• 173143-86-7 (1R,6S,7R)-7-Methyl-7-(4-methyl-pent-3-enyl)-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester 
• 28624-15-9 (E)-2-[2-Hydroxy-eth-(E)-ylidene]-6,10-dimethyl-undeca-5,9-dienoic acid 
• 28624-17-1 (E)-6,10-Dimethyl-2-[2-oxo-eth-(E)-ylidene]-undeca-5,9-dienoic acid methyl ester 
• 28624-16-0 (E)-2-[2-Hydroxy-eth-(E)-ylidene]-6,10-dimethyl-undeca-5,9-dienoic acid methyl ester 
• 28624-19-3 (E)-2-[2-Diazo-eth-(E)-ylidene]-6,10-dimethyl-undeca-5,9-dienoic acid methyl ester 
• 99968-60-2 methyl (E)-4-bromo-2-methylbut-2-enoate 
• 76062-92-5 2-hydroxy-2-methyl-3-butenoic acid methyl ester 
• 31572-04-0 2-hydroxy-2-methylbuten-3-oic acid 
• 23635-14-5 (s)-(-)-perillic acid 
• 26460-67-3 (S)-methylperillate 
• 18031-40-8 (S)-(-)-perillaldehyde 

Relevant articles and documents

The first enantioselective synthesis of the chemotactic factor sirenin by an intramolecular [2 + 1] cyclization using a new chiral catalyst

A simple, highly enantioselective synthesis of sirenin (1) (bioactive form) has been developed which depends on the intramolecular [2 + 1] cycloaddition reaction of diazo ester 5 to form bicyclic ester 6 (95:5 enantioselectivity) using a new and remarkably stable monomeric chiral Cu(I) complex (2) whose structure was proven by X-ray diffraction analysis.

THE SYNTHESIS OF (-)-SIRENIN, SPERM ATTRACTANT OF THE WATER MOLD ALLOMYCES MACROGYNUS

Synthesis of (-)-sirenin 1a, sperm attracting hormone of Allomyces macrogynus was achieved through 10 steps from (-)-perillaldehyde 3.Formation of cyclopropane ring was executed diastereoselectively by the cyclization via intramolecular epoxide opening under carefully controlled condition.

A NEW TOTAL SYNTHESIS OF DL-SIRENIN

A new total synthesis of dl-sirenin (1) has been effectively accomplished by employing the acetate 4a obtained by the stereoselective rearrangenent of the acetate 3 using a palladium catalyst.