1224174-07-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-chlorohept-6-en-2-ol is used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure and properties make it a valuable building block for the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
(S)-1-chlorohept-6-en-2-ol is also utilized as an intermediate in the production of agrochemicals. Its role in the synthesis of various agrochemical products highlights its versatility and importance in the agricultural sector.
Used in Fragrance Industry:
(S)-1-chlorohept-6-en-2-ol is employed in the fragrance industry as an intermediate for creating different types of scents. Its contribution to the development of new fragrances adds to its significance in the industry.
Safety Precautions:
It is crucial to handle (S)-1-chlorohept-6-en-2-ol with care due to its toxic nature. Exposure to (S)-1-chlorohept-6-en-2-ol can cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken to minimize the risk of adverse health effects.

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 693-03-8 n-butyl magnesium bromide 
• 5162-44-7 1-bromo-4-butene 

Downstream Products

• 1350619-77-0 (1R,2R)-2-(pent-4-yn-1-yl)cyclopropan-1-ol 
• 1425038-19-2 (S)-3,3-dimethyl-2-(((1R,2R)-2-(pent-4-ynyl)cyclopropoxy)carbonylamino)butanoic acid 
• 1425038-21-6 (S)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-yn-1-yl)cyclopropoxy)carbonyl)amino)butanoic acid tert-butylamine salt 
• 1425038-23-8 methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-18,19-didehydro-1,1a,3,4,5,6,9,10,20,21,22,22a-dodecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3, 6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate 
• 1206524-84-6 methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxa-diazacyclononadecino[11,12-b]quinoxaline-8-carboxylate 
• 1206524-85-7 (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradeca-hydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid hydrate 
• 1350514-68-9 grazoprevir 

Relevant academic research and scientific papers

Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir

A practical and asymmetric synthesis of a functionalized trans-cyclopropoxy building block for the preparation of the HCV NS3/4a protease inhibitor grazoprevir is reported. Intramolecular SN2 displacement-ring closure, followed by a Baeyer-Villiger oxidation, yields the desired trans-cyclopropanol with full control of diastereoselectivity. A terminal alkyne is then effectively installed using LiNH(CH2)2NEt2. Starting from (S)-epichlorohydrin, the cyclopropoxy building block is prepared in 51% overall yield with >99.8% optical purity without isolation of any intermediates.

Efficient total synthesis of (+)-dihydropinidine, (-)-epidihydropinidine, and (-)-pinidinone

The 2,6-disubstituted piperidine alkaloids (+)-dihydropinidine (1), (-)-epidihydropinidine (2) (as HCl salts), and (-)-pinidinone (3) were efficiently synthesized from (S)-epichlorohydrin (7) as common substrate using regioselective Wacker-Tsuji oxidation of alkenylazides 10 and 14 as well as a highly diastereoselective reduction of cyclic imine 11 as key steps. The protecting group free total syntheses represent the up to date shortest routes with highest overall yields for all three naturally occurring alkaloids (1-3). The first single-crystal X-ray analysis of (-)-epidihydropinidine hydrochloride (2 · HCl) confirmed its proposed absolute configuration to be (2S,6S), corresponding to that of the isolated natural product.

METHODS AND INTERMEDIATES FOR PREPARING MACROLACTAMS

The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. HCV NS3 inhibitory compounds have therapeutic and research applications.

Synthesis of 2,6-disubstituted piperidine alkaloids from ladybird beetles Calvia 10-guttata and Calvia 14-guttata

Optically pure (+)-calvine, (+)-2-epicalvine, (2S,6S)-(6-pentylpiperidin-2-yl)acetic acid methyl ester and (2R,6S)-(6-pentylpiperidin-2-yl)acetic acid methyl ester, four piperidine alkaloids isolated from ladybird beetles of the genus Calvia (Coccinellidae), were synthesised from a common precursor using cyclisative Pd(II)/Cu(II)-catalysed carboamination-(methoxy)carbonylation tandem reaction of alkenylamines as a key step. The first single-crystal X-ray analysis of (+)-calvine confirmed its proposed absolute configuration to be (2S,6S) corresponding to that of natural product.