76739-64-5

Basic information

• Product Name: (1S)-1,4,4,6-tetramethyl-2,3-dihydro-1H,4H-3a,6a-propanopentalene
• CAS NO: 76739-64-5
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• Mol File: 76739-64-5.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 267.5°C at 760 mmHg
• Flash Point: 113.8°C
• Density: 0.95g/cm³
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: (1S)-1,4,4,6-tetramethyl-2,3-dihydro-1H,4H-3a,6a-propanopentalene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-1,4,4,6-tetramethyl-2,3-dihydro-1H,4H-3a,6a-propanopentalene(76739-64-5)
• EPA Substance Registry System: (1S)-1,4,4,6-tetramethyl-2,3-dihydro-1H,4H-3a,6a-propanopentalene(76739-64-5)

Safety Data

• Hazardous Substances Data: 76739-64-5(Hazardous Substances Data)

Upstream product

• 122437-20-1 (5R*,6S*,7S*)-6,7,11,11-tetramethyldispiro<3.0.4.2>undecan-6-ol 
• 76685-67-1 (3aS,6aS)-3,6-Dimethyl-5,6-dihydro-4H-3a,6a-propano-pentalen-1-one 
• 99304-62-8 C₁₄H₂₀O 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 849180-44-5 1-(1-but-3-enyl-2-methylene-cyclopentyl)-ethanol 
• 849180-35-4 1-(1-but-3-enyl-2-methylene-cyclopentyl)-ethanone 
• 849180-34-3 (1-but-3-enyl-2-methylene-cyclopentyl)-methanol 
• 849180-10-5 1-but-3-enyl-2-methylene-cyclopentanecarbaldehyde 
• 82343-68-8 (butene-3-yl)-1 oxo-2 cyclopentanecarboxylate de methyle 
• 849180-11-6 2-(1-but-3-enyl-2-methylene-cyclopentyl)-pent-4-yn-2-ol 

Relevant articles and documents

A Total Synthesis of (+/-)-Modhephene

A new approach to the propellane system via a key photochemical oxa-di-?-methane rearrangement has culminated in a synthesis of the sesquiterpene hydrocarbon (+/-)-modhephene (1).

Total Synthesis of (+/-)-Modhephene

-

Short, Stereospecific Total Syntheses of (+/-)-Modhephene and (+/-)-Epimodhephene

-

Synthesis of the naturally occurring [3.3.3]propellane (±)-modhephene featuring a photocycloaddition-reductive fragmentation diquinane construction

Modhephene has been synthesized in 11 steps and 21% overall yield from cyclopentadiene, by a stereoselective route that features a photocycloaddition-fragmentation sequence for the construction of the diquinane core.

HIGHLY STEREOCONTROLLED SYNTHESIS OF PROPELLANE SESQUITERPENES. (+/-)-MODHEPHENE AND (+/-)-EPIMODEPHENE

Stereospecific total synthesis of (+/-)-modhephene (2) and (+/-)-epimodhephene are reported.Conjugate addition of 1-trimethylsilyl-1-butyn-4-yl cuprate (BF3-etherate catalysis) to bicyclic ketone 6, fluoride ion-promoted deblocking of the terminal acetylene, and ene reaction, gave tricyclic enone 11.Sequential Wittig methylenation, regiocontrolled epoxidation, and Lewis acid catalyzed isomerization afforded ketone 14 whose double bond relocation and Wolff-Kishner reduction led exclusively to 2.In a still shorter route to 3,3-butelyl cuprate addition to 6 was utilized to gain access to 7.Thermolysis of this intermediate, methylenation, and double bond isomerization were found to deliver pure 3 successfully.

Synthesis of tricyclopentanoid sesquiterpenes via rearrangement routes: (±)-modhephene, (±)-epimodhephene and (±)-isocomene

Based on model studies with dispiroundecane 10, dispiroundecane 1 has been synthesized and rearranged to (±)-modhephene 6 and (±)-isocomene 7. The epimeric dispiroundecane 9 yields (±)-epimodhephene 12. A total of thirteen rearrangement products (6, 7, 12, 37, 38, 39, 42, 44, 55, 57, 64, 67) have been isolated from 1 and/or 9, including six unnatural triquinanes. Two of these (55, 57) are formed by unusual 1,3- and 1,4-shifts, respectively. A mechanistic rationale on the basis of force field calculations is given.