6567-98-2

Basic information

• Product Name: 1,2-epoxyoctahydropentalene
• Synonyms: 1,2-epoxyoctahydropentalene;Octahydropentaleno[1,2-b]oxirene
• CAS NO: 6567-98-2
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18028
• EINECS: 229-489-0
• Mol File: 6567-98-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 184.6°C at 760 mmHg
• Flash Point: 45.7°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 0.997mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 1,2-epoxyoctahydropentalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-epoxyoctahydropentalene(6567-98-2)
• EPA Substance Registry System: 1,2-epoxyoctahydropentalene(6567-98-2)

Safety Data

• Hazardous Substances Data: 6567-98-2(Hazardous Substances Data)

Usage

Type of compound

Bicyclic hydrocarbon

Functional group

Cyclic ether

Reactivity

Versatile, can undergo ring-opening reactions

Applications

a. Organic synthesis as a building block for various compounds
b. Production of fragrances and flavors
c. Pharmaceutical industry
d. Agrochemical industry

Importance

Valuable intermediate in the synthesis of complex organic molecules due to its unique structure and reactivity

InChI:InChI=1/C8H12O/c1-2-5-4-7-8(9-7)6(5)3-1/h5-8H,1-4H2

Upstream product

• 5549-09-7 bicyclo[3.3.0]oct-2-ene 
• 930-99-4 (3aS,6aS)-1,2,3,3a,4,6a-Hexahydro-pentalene 

Downstream Products

• 1551-76-4 exo-2-methyl-cis-bicyclo<3.3.0>octane 

Relevant articles and documents

Mitsunobu Reaction of Unbiased Cyclic Allylic Alcohols

The stereochemical inversion of unbiased allylic alcohols using triphenylphosphine, diethyl azodicarboxylate, and benzoic acid, commonly known as the Mitsunobu reaction, was studied in three different solvents with specific attention toward the product composition. The results generated for the Mitsunobu reaction of (R)-3-deuterio-2-cyclohexen-1-ol and the cis and trans isomers of 1-deuterio-5-methyl-2-cyclohexen-1-ol, 1-deuterio-5-tert-butyl-2-cyclohexen-1-ol, and optically active cis and trans 5-isopropyl-2-methyl-2-cyclohexen-1-ol all gave similar product distributions with respect to inversion and retention at the carbinol center as well-as syn and anti Sn2′ type addition when THF or benzene was used as the solvent (CH2Cl2 gave less selective product distributions). Interestingly, it was found that the quasi-equatorial and quasi-axial nature of the starting allylic alcohol does not appear to affect the product distribution for this reaction, nor does methyl substitution at the central carbon of the allylic alcohol. In all cases, significant amounts (8-28%) of non-SN2 type products were detected for these sterically unbiased allylic alcohols; only 72-77% of the product was from SN2 type reaction when sterically undemanding (R)-S-deuterio-2-cyclohexen-1-ol was subjected to Mitsunobu conditions.

THERMAL REARRANGEMENT OF DIVINYLCYCLOPROPANE SYSTEMS. PREPARATION OF FUNCTIONALIZED, STEREOCHEMICALLY DEFINED BICYCLIC AND TRICYCLIC PRODUCTS CONTAINING THE BICYCLOOCTANE SKELETON

A study involving the preparation and thermolysis of substituted 6-exo-(1-alkenyl)bicyclohex-2-ene systems (14, 15, 23, 29, 40) shows (a) that C-8 functionalized bicycloocta-2,6-dienes can be prepared readily via this methodology (14 -> 16; 15 -> 17), (b) that the rearrangement reaction is stereospecific even when the 6-(1-alkenyl) group is substituted with a sterically bulky isopropyl group (23 -> 24; 29 -> 30), and (c) that the method can be extended to include the preparation of tricyclic systems (40 -> 41).