71242-58-5

Basic information

• Product Name: (1S)-(-)-10-MERCAPTOISOBORNEOL
• Synonyms: (1S)-(-)-10-MERCAPTOISOBORNEOL;Mercaptoisoborneol;(1S)-(-)-10-MERCAPTOISOBORNEOL 98+%;(-)-10-Mercaptoisoborneol;(+)-10-Mercaptoisoborneol;(1S,2R,4R)-1-(Mercaptomethyl)-7,7-dimethylbicyclo[2.2.1]heptane-2-ol;(1S,4R)-6β-Hydroxybornane-10-thiol;(4α)-1β-(Mercaptomethyl)-7,7-dimethylbicyclo[2.2.1]heptane-2α-ol
• CAS NO: 71242-58-5
• Molecular Formula: C₁₀H₁₈OS
• Molecular Weight: 186.31
• Product Categories: Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Synthetic Organic Chemistry;Terpenes
• Mol File: 71242-58-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 72 °C
• Appearance: /
• Refractive Index: 1.543
• Solubility: almost transparency in Chloroform
• CAS DataBase Reference: (1S)-(-)-10-MERCAPTOISOBORNEOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(-)-10-MERCAPTOISOBORNEOL(71242-58-5)
• EPA Substance Registry System: (1S)-(-)-10-MERCAPTOISOBORNEOL(71242-58-5)

Safety Data

• Hazardous Substances Data: 71242-58-5(Hazardous Substances Data)

Usage

Description

(1S)-(-)-10-Mercaptoisoborneol, a chiral compound and a derivative of borneol, is a monoterpene alcohol that features a thiol functional group. Characterized by its minty aroma, this versatile chemical finds applications in various industries, including fragrances, chemical synthesis, and potentially pharmaceuticals, due to its unique properties and stereochemistry.

Uses

Used in Fragrance Industry:
(1S)-(-)-10-Mercaptoisoborneol is used as a fragrance ingredient for its characteristic minty aroma, adding a refreshing scent to various products.
Used in Asymmetric Synthesis:
In the field of chemical synthesis, (1S)-(-)-10-Mercaptoisoborneol serves as a chiral auxiliary, playing a crucial role in controlling the stereochemistry of reactions and facilitating the production of enantiomerically pure compounds.
Used in Pharmaceutical Applications:
(1S)-(-)-10-Mercaptoisoborneol is studied for its potential as an antioxidant and anti-inflammatory agent, showcasing its promise in the development of new pharmaceuticals.
Due to its chirality, (1S)-(-)-10-Mercaptoisoborneol exhibits different biological activities based on its stereochemistry, further expanding its range of applications across various industries.

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-/m1/s1

Upstream product

• 4552-50-5 camphorsulfonyl chloride 
• 21286-54-4 Camphorsulfonyl chloride 
• 129887-41-8 (+)-(1R,R_S)-2-exo-<((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl)methylsulphinyl>-3-endo-hydroxymethylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid lactone 
• 129887-42-9 (1S,2S,6R,7R)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 4552-50-5 (1S)-(+)-10-Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 121611-73-2 (1R,2R,3S,4S)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 
• 121611-72-1 dimethyl (R_S)-2-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)maleate 
• 121701-13-1 (1S,2S,3R,4R)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 
• 54984-43-9 (1S,4R)-camphor-10-thiol 

Downstream Products

• 1439-07-2 (R,R)-trans-stilbene epoxide 
• 129432-63-9 (1S,4S,6R,8R)-11,11-Dimethyl-4-phenyl-5-oxa-3-thia-4-phospha-tricyclo[6.2.1.0^1,6]undecane 4-oxide 
• 129432-63-9 (1S,4R,6R,8R)-11,11-Dimethyl-4-phenyl-5-oxa-3-thia-4-phospha-tricyclo[6.2.1.0^1,6]undecane 4-oxide 
• 132345-22-3 α-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylthio)-N-phenylsuccinimide 
• 132374-44-8 N-benzyl-α-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylthio)succinimide 
• 127891-50-3 (E)-(1S,2R,4R)7,7-dimethyl-1-<(2'-phenylethenyl)thio>methyl-bicyclo<2.2.1>heptan-2-ol 
• 99894-19-6 (1S,2R,4R)-1-((Z)-2-Benzenesulfonyl-vinylsulfanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 129432-69-5 (1S,4S,6R,8R)-11,11-Dimethyl-4-phenylsulfanylmethyl-5-oxa-3-thia-4-phospha-tricyclo[6.2.1.0^1,6]undecane 4-oxide 
• 129432-69-5 (1S,4R,6R,8R)-11,11-Dimethyl-4-phenylsulfanylmethyl-5-oxa-3-thia-4-phospha-tricyclo[6.2.1.0^1,6]undecane 4-oxide 
• 99908-18-6 (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 129432-65-1 (1S,4S,6R,8R)-4-Benzyl-11,11-dimethyl-5-oxa-3-thia-4-phospha-tricyclo[6.2.1.0^1,6]undecane 4-oxide 
• 129432-65-1 (1S,4R,6R,8R)-4-Benzyl-11,11-dimethyl-5-oxa-3-thia-4-phospha-tricyclo[6.2.1.0^1,6]undecane 4-oxide 
• 135227-12-2 (S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone 
• 129839-93-6 (1S,2R,4R)-1-Benzylsulfanylmethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 

Relevant articles and documents

The Use of Chiral Sulfides in Catalytic Asymmetric Epoxidation

Non racemic epoxides with ee's of 23-41percent have been prepared from aldehydes and phenyl diazomethane using catalytic amounts of sulfides derived from camphor.

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.