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

General Description

(1S)-(-)-10-Mercaptoisoborneol is a chiral compound and a derivative of borneol. It is a monoterpene alcohol which contains a thiol functional group. (1S)-(-)-10-MERCAPTOISOBORNEOL has a characteristic minty aroma and is often used in the fragrance industry. It is also utilized as a chiral auxiliary in asymmetric synthesis to control the stereochemistry of reactions. Additionally, (1S)-(-)-10-Mercaptoisoborneol has been studied for its potential pharmaceutical applications, including as an antioxidant and anti-inflammatory agent. Due to its chirality, this compound has the ability to exhibit different biological activities based on the stereochemistry. Overall, (1S)-(-)-10-Mercaptoisoborneol is a versatile chemical with various uses in fragrance, chemical synthesis, and potentially in pharmaceuticals.

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 
• 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 
• 21286-54-4 Camphorsulfonyl chloride 
• 54984-43-9 (1S,4R)-camphor-10-thiol 
• 121611-72-1 dimethyl (R_S)-2-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)maleate 
• 4552-50-5 (1S)-(+)-10-Camphorsulfonyl chloride 
• 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 
• 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 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 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 

Downstream Products

• 127891-50-3 (E)-(1S,2R,4R)7,7-dimethyl-1-<(2'-phenylethenyl)thio>methyl-bicyclo<2.2.1>heptan-2-ol 
• 99908-18-6 (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 129839-95-8 (1S,2R,4R)-7,7-Dimethyl-1-phenethylsulfanylmethyl-bicyclo[2.2.1]heptan-2-ol 
• 185855-96-3 (2S,4R)-4-[(1S,4R)-2-oxobornane-10-sulfenyl]-4-phenyl-2-butanol 
• 185856-02-4 4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-4-phenyl-butan-2-one 
• 370570-02-8 (2R)-benzyl 3-[(1S,2R,4R)-2-hydroxybornane-10-sulfenyl]-2-methylpropionate 
• 370570-11-9 (R)-N-(4-Chloro-phenyl)-3-((1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-2-methyl-propionamide 
• 501700-70-5 (1S,4R,6R,8R)-11,11-dimethyl-4-[(E)-2-phenyl-propenyl]-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane 
• 99894-21-0 1-((Z)-2-Benzenesulfonyl-ethenesulfinylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 103953-50-0 (1S,4R,6R,8R)-4-Benzenesulfonylmethyl-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane 3-oxide 
• 104012-55-7 (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-ethenesulfinylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 103953-51-1 (1S,4R,6R,8R)-4-Benzenesulfonylmethyl-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane 3,3-dioxide 
• 103953-52-2 (1S,4R,6R,8R)-4-(4-Chloro-benzenesulfonylmethyl)-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane 3-oxide 
• 103953-53-3 (1S,4R,6R,8R)-4-(4-Chloro-benzenesulfonylmethyl)-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane 3,3-dioxide 

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.