71242-59-6

Basic information

• Product Name: (1S)-(-)-10-MERCAPTOBORNEOL
• Synonyms: (1S)-(-)-10-MERCAPTOBORNEOL;Mercaptoborneol;(1S)-(-)-10-MERCAPTOBORNEOL 97+%;(1S)-(-)-10-Mercaptoborneol
• CAS NO: 71242-59-6
• Molecular Formula: C₁₀H₁₈OS
• Molecular Weight: 186.31
• Mol File: 71242-59-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 86 °C
• Appearance: /
• Refractive Index: -6 ° (C=2, CHCl3)
• CAS DataBase Reference: (1S)-(-)-10-MERCAPTOBORNEOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(-)-10-MERCAPTOBORNEOL(71242-59-6)
• EPA Substance Registry System: (1S)-(-)-10-MERCAPTOBORNEOL(71242-59-6)

Safety Data

• Hazardous Substances Data: 71242-59-6(Hazardous Substances Data)

Usage

General Description

(1S)-(-)-10-Mercaptoborneol is a chemical compound with the molecular formula C10H18OS. It is a chiral compound, with the (1S)-(-) enantiomer being the most commonly used form. This chemical is a sulfur-containing alcohol, with a thiol group (-SH) attached to a ten-membered ring structure. It is used in organic synthesis as a chiral auxiliary, and as a building block for the synthesis of other chiral compounds. The compound has a characteristic camphor-like odor and is often used as a scent in perfumes and personal care products. Additionally, it has been studied for its potential biological and pharmaceutical applications, including as an agent for the treatment of neurological disorders.

InChI:InChI=1/C10H18OS/c1-9(2)7-3-4-10(9,6-12)8(11)5-7/h7-8,11-12H,3-6H2,1-2H3/t7?,8?,10-/m0/s1

Upstream product

• 4552-50-5 camphorsulfonyl chloride 
• 21286-54-4 Camphorsulfonyl chloride 
• 4552-50-5 (1S)-(+)-10-Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Downstream Products

• 1439-07-2 (R,R)-trans-stilbene epoxide 

Relevant articles and documents

Process for the preparation of an oxirane, aziridine or cyclopropane

A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I), wherein X is oxygen, NR4or CHR5; R1is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R2is hydrogen, alkyl, aryl, heteroaromatic, CO2R8, CHR14NHR13, heterocyclic or cycloalkyl; or R1and R2join together to form a cycloalkyl ring; R3and R10are, independently, hydrogen, alkyl, aryl, heteroaromatic, CO2R8, R83Sn, CONR8R9, trialkylsilyl or triarylsilyl; R4is an electron withdrawing group; R5is alkyl, cycloalkyl, aryl, heteroaromatic, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2or CN; R8and R9are independently alkyl or aryl; and R13and R14are independently hydrogen, alkyl or aryl is provided. The process comprises degrading a compound of formula (II), (IIa), (IIb) or (IIc): wherein R3and R10are as defined above; Y is a cation; depending on the nature of Y, r is 1 or 2; and L is a suitable leaving group, to form a diazo compound. The diazo compound is reacted with a suitable transition metal catalyst, and the product thereof reacted with a sulphide of formula SR6R7, wherein R6and R7are independently alkyl, aryl or heteroaromatic, or R6and R7join together to form an optionally substituted ring which optionally includes an additional heteroatom. This product is then reacted with an aldehyde, ketone, imine or alkene.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

A New Resolution Procedure for the Preparation of Both (R)-(+)- and (S)-(-)-4-tert-Butoxycyclopent-2-enone from Racemic 4-tert-Butoxycyclopent-2-enone and Conversion of (R)-(+)-Butoxycyclopent-2-enone into (R)-(+)-4-Acetoxycyclopent-2-enone. A New Method for the Determination of the ...

(1S)-(-)-10-Mercaptoisoborneol undergoes conjugate addition to (+/-)-4-tert-butoxycyclopent-2-enone in methanol containing N,N,N',N'-tetramethylethylenediamine to give a 1:1 mixture of diastereomers of 3-tert-butoxy-4-heptanyl)methyl>thio>cyclopentanone in 93-95percent yield.The mixture is converted by m-chloroperbenzoic acid into the corresponding sulfoxide mixture.The (3R,4R,RS)-sulfoxide isomer, whose absolute configuration has been determined by X-ray crystallography, crystallizes cleanly from this mixture in an enantiomeric yield of 76percent from the corresponding sulfide.It is decomposed on silica gel to generate (R)-(+)-4-tert-butoxycyclopent-2-enone, with an enantiomeric purity of >/- 99.9percent in 92percent yield from the sulfoxide, and 10-thiodiisobornyl 10'-sulfoxide.Similarly, the (S)-(-)-enone is prepared from (1R)-(+)-10-mercaptoisoborneol.The (+/-) and the (R)-(+)-enone, respectively, are converted by a catalytic amount of FeCl3 in acetic anhydride into (+/-) and (R)-(+)-4-acetoxycyclopent-2-enone (with an enantiomeric purity of >/- 99.9percent) in 80percent yield.The enantiomeric purity of the products was assessed through their treatment with (-)-10-mercaptoisoborneol and analysis of the adducts by HPLC and 400-MHz 1H NMR spectroscopy.