4729-05-9

Usage

Uses

Used in Fragrance Industry:
(1S,1α,5α)-Bicyclo[3.1.0]hexa-2-ene-6β-carbaldehyde is used as a key ingredient in perfumes, soaps, and cosmetics for its characteristic woody, fruity, and floral scent that adds depth and complexity to fragrance compositions.
Used in Therapeutic Applications:
(1S,1α,5α)-Bicyclo[3.1.0]hexa-2-ene-6β-carbaldehyde is used as an antimicrobial, anti-inflammatory, and antioxidant agent for its potential therapeutic properties, which can contribute to the development of new treatments and remedies.
Used in Skin Care Products:
(1S,1α,5α)-Bicyclo[3.1.0]hexa-2-ene-6β-carbaldehyde is used as a soothing and anti-aging agent in skin care products, taking advantage of its potential to provide skin health benefits and improve the overall appearance of the skin.

Upstream product

• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 278-06-8 quadricyclo[2.2.1.0.0]heptane 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 5307-99-3 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 20836-85-5 7-endo-chlorobicyclo<3.2.0>hept-2-en-6-one 
• 53670-43-2 (1R,5S,6S,7R)-7-Chloro-bicyclo[3.2.0]hept-2-en-6-ol 
• 278-06-8 tetracyclo-[3.2.0.0.^2,7.0^4,6]heptane 

Downstream Products

• 4729-05-9 bicyclo[3.1.0]hex-2-en-6-endo-carboxaldehyde 
• 101166-07-8 endo-6-<(Z)-2-Phenylvinyl>bicyclo<3.1.0>hex-2-en 
• 101165-89-3 endo-4-Phenylbicyclo<3.2.1>octa-2,6-dien 
• 101166-08-9 2-Phenylbicyclo<3.2.1>octa-2,6-dien 
• 101166-09-0 2-Phenyl-<4,4-D2>bicyclo<3.2.1>octa-2,6-dien 
• 101165-90-6 exo-4-Phenylbicyclo<3.2.1>octa-2,6-dien 
• 4971-26-0 bicyclo<3.1.0>hex-2-ene-endo-6-carboxylic acid 
• 4971-26-0 1α,5α,6α-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid 
• 98973-68-3 Bicyclo<3.1.0>hex-2-en-6-endo-carbonsaeurechlorid 
• 60153-55-1 6-endo-(Benzyloxymethyl)bicyclo<3.1.0>hexan-3-on 

Relevant academic research and scientific papers

PYRAZOLYLPYRIDINE ANTIVIRAL AGENTS

Provided are compounds of Formula (I) and/or Formula (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

Blocking fluorine substitution in biotransformation of nortricyclanyl N-phenylcarbamates with Beauveria bassiana

The biotransformation of tricyclo[2,2,1,02,6]hept-3-yl N-phenylcarbamate (8) by a standard procedure using Beauveria bassiana gave a 7:1 mixture of optically active exo,exo- and exo,endo-5-hydroxytricyclo[2.2.1.02,6]hept-3-yl N-phenylcarbamates 15 and 16 in 19% isolated yield. No ring opening of the three-membered ring was observed. Substitution with a fluorine atom at the 5-endo- or 5-exo-position prevented hydroxylation of any alicyclic position of the molecules, p-hydroxylation of the aromatic ring occurring to a small extent instead. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

An efficient synthesis of (±)-cis-2-mino-6-hydroxy-9[4'-hydroxyethyl- 2'-cyclopenten-1'-yl]purine

The synthesis of a carbovir analogue, (±)-cis-2-amino-6-hydroxy-9- [4'hydroxyethyl-2'-cyclopenten-l'-yl]purine (2) was achieved from 2,5- norbornadiene (3) in six steps and 31% overall yield. This route involves a Meinwald rearrangement, one-pot operation (acid-hydrolysis and subsequent sodium borohydride reduction), and a Pd(0)catalyzed coupling reaction.

Reactions of Microwave-Generated O(3P) Atoms with Unsaturated Hydrocarbons

The reactions of neat olefins or solutions of olefins in acetone at low temperature with oxygen atoms were examined. O(3P) atoms were produced by microwave irradiation of He/O2 mixtures, followed by contact of the plasma with the fluid at low pressure and temperature. Addition of oxygen atoms to olefins results in skeletal rearrangements involving hydrogen and alkyl migration reactions and ring rearrangements of the intermediate oxygen adducts in competition with epoxide formation. While epoxide formation predominates for simple olefins such as 1- and 4-octene with minor yields of rearrangement products, for highly substituted or strained olefins, such as norbornadiene, skeletal rearrangement dominates following oxygen atom addition. When oxidation of norbornadiene is carried out in the presence of a radical inhibitor to suppress secondary oxidation leading to benzene, the novel ring-rearrangement product, bicyclo[3.2,31.0]hex- 3-ene-endo-6-carboxaldehyde, is produced from norbornadiene in significant yields.

Generation of [5.5.n] Tricyclic Ring Systems by Radical-Promoted Inter- And Intramolecular [3 + 2] Cycloadditions

A new method for the synthesis of [5.5.n] tricyclic ring systems via radical fragmentation and double cyclization is described. The general process (Scheme 1) involves addition of an alkylthio radical to an alkenylcyclopropane 1 to generate the cyclopropylcarbinyl radical which opens to the homoallylic radical; this radical then adds to an alkene or alkyne radical trap to give a new alkyl radical which then adds back to the thioalkyl allylic system to generate, after loss of the alkylthio radical, the bi- or tricyclic product, 2, thus making the process analogous to a [3 + 2] cycloaddition. Thus addition of the butylthio radical (generated by photolysis of dibutyl disulfide) to the bicyclo-[3.1.0]hex-2-en-6-yl carboxylate 3 in the presence of an alkene or alkyne-either an acyclic radical trap, e.g., ethyl vinyl ether, isopropenyl acetate, methyl acrytate, or methyl propiolate, or a cyclic one, e.g., cyclopentenone, dihydrofuran, cyclopentenyl acetate, or cyclopentene-affords the desired bi- or tricyclic products 9-16 in yields of 54-88%. One can also use 6-vinylbicyclo[3.1.0]hexan-2-one (4) as the alkenylcyclopropane unit. Trapping of the radical generated by addition of butylthio radical to 4 with ethyl vinyl ether or cyclopentene affords the bi- and tricyclic products 17 and 18 in 66-68% yields. The products are formed as diastereomeric mixtures in all cases. This cyclization process can also be carried out in an intramolecular fashion, e.g., isomerization of the ketones 25 and 27 or the esters 28-30 with butylthio radical to give the tricyclic products 31-35 and 41-43. The use of dimethyl-substituted alkenes gives reasonably good diastereoselectivity favoring the cis-syn-cis isomer over the cis-anti-cis isomer, e.g., 7.5:1 for 33 over 34 and 4.2:1 for 41 over 42. The structures of the diastereomeric products were proven by comparison of the NMR spectra of the saturated analogues, which are known for the unsubstituted series and differ in their symmetry properties for the dimethyl-substituted case. These results indicate that the cyclization of a stabilized 5-hexenyl radical, e.g., 45 in Scheme 8, is reversible and leads to the most stable final product.

Chemistry of Dioxiranes. 10. Oxidation of Quadricyclane and Norbornadiene by Dimethyldioxirane

Treatment of quadricyclane (2) with dimethyldioxirane (1) leads to the formation of exo-norborna-2,5-diene monoepoxide (4), exo,exo-norborna-2,5-diene diepoxide (5), bicyclohex-2-ene-6-endo-carboxaldehyde (6), and exo-2,3-epoxybicyclohexane-6-endo-carboxaldehyde(7).The reaction is believed to involve prior catalyzed isomerization of 2 by 1 to norbornadiene (3) and subsequent conversion of 3 to the observed products.Under suitable conditions 1 reacts with 3 to give 4 and 6 in a 97:3 distribution, respectively.

2-Decarboxy-2-amino-methyl-PGE and PGD analogs

Prostaglandin analogs wherein the C-2 carboxy is replaced by an aminomethyl or (substituted amino)methyl are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for the same pharmacological purposes as the prostaglandins.

Aliphatic 2-decarboxy-2-hydroxymethyl-13,14-didehydro-PG compounds

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

13,14-Didehydro-PG3 compounds

This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.