578006-81-2

Basic information

• Product Name: Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]-
• CAS NO: 578006-81-2
• Molecular Formula: C16H22O
• Molecular Weight: 230.35
• Mol File: 578006-81-2.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]-(578006-81-2)
• EPA Substance Registry System: Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]-(578006-81-2)

Safety Data

• Hazardous Substances Data: 578006-81-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]is utilized as an intermediate in the production of pharmaceuticals. Its role in organic synthesis allows for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]is employed as a key component in the synthesis of various agrochemical products. Its presence in these compounds can enhance the effectiveness of pesticides, herbicides, and other agricultural chemicals, thereby improving crop protection and yield.
Used in Flavor and Fragrance Industry:
Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]is also used as a component in the flavor and fragrance industry. Its unique chemical properties contribute to the creation of distinct scents and flavors, making it an essential ingredient in the formulation of perfumes, cosmetics, and food flavorings.
Used in Organic Synthesis:
Ethanone, 1-phenyl-2-[(1R,3S)-2,2,3-trimethylcyclopentyl]is a versatile building block in organic synthesis. Its structure and reactivity enable the formation of a diverse array of complex molecules, which are crucial in the development of new materials, compounds, and chemical products across various industries.

Upstream product

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 31503-04-5 Phenylborneol 

Downstream Products

• 581094-59-9 (1S,3S)-2,2,3-trimethyl-cyclopentanecarboxylic acid 
• 791104-73-9 1-(3-nitrophenyl)-2-[(1R,3S)-2,2,3-trimethylcyclopent-1-yl]ethan-1-one 

Relevant articles and documents

Thermal isomerization of isoborneols and dehydroisoborneols to new chiral building blocks in terpenoid synthesis

The substituted isoborneols 1a-1g and 5,6-dehydroisoborneols 6a-6c, readily prepared in excellent yields from (+)-camphor and (+)-5,6-dehydrocamphor (2) by aryl, vinyl, or alkyl Grignard addition in the presence of stoichiometric amounts of CeCl3, were thermally isomerized in a flow reactor system under DGPTI (dynamic gas-phase thermo-isomerization) conditions at temperatures between 480 and 630° to give the enantiomerically pure monocyclic carbonyl compounds 7a-7d, 19a,b, 23, and 24. In all cases, product formation proceeded highly regio- as well as stereoselectively. The absolute configurations of the new stereogenic centers were determined by 1H-NOE measurements. DGPTI of the aryl substrates 1a-1d is proposed to effect initial cleavage of the weakest single bond in the molecule under formation of a diradical intermediate state followed by intramolecular H-abstraction to afford the acetophenone derivatives 7a-7d. This reaction path was further supported by a 2H-labeling study showing the OH group to be the exclusive H-source. In contrast, DGPTI of the vinyl substrates 1e and 6b allowed concerted retro-ene and oxy-Cope rearrangements. In the case of 5,6-dehydro-2-phenylisoborneol (6a), concomitant diradical and retro-Diels-Alder reaction pathways could be observed. In addition, a new route to (+)-rrans-a-campholanic acid (9) and (+)-trans-a-dihydrocampholytic acid (14) is presented by regioselective Baeyer-Villiger oxidation and subsequent hydrolysis of 7c and 7d, respectively.

Stereo- and regioselectivity in dynamic gas-phase thermoisomerization (DGPTI): Novel route to α-campholanic acid and derivatives

(Matrix presented) Dynamic gas-phase thermoisomerization (DGPTI) of (-)-2-phenylisoborneols effects stereo- and regioselective ring opening under formation of (+)-trans-α-campholanic acid derivatives. Similarly, (-)-α-2-phenylfenchol underwent under DGPTI conditions ring opening to (-)-fencholic acid derivatives. In both cases, DGPTI led to cleavage of the weakest bond in the isomeric bicyclic structures. A reaction mechanism involving a diradical intermediate is supported by a deuterium labeling study.