(1S)-(-)-10-Mercaptoborneol

Base Information

• Chemical Name: (1S)-(-)-10-Mercaptoborneol
• CAS No.: 71242-58-5
• Molecular Formula: C10H18 O S
• Molecular Weight: 186.318
• Hs Code.: 2930909899
• DSSTox Substance ID: DTXSID10541393
• Nikkaji Number: J1.830.872J
• Mol file: 71242-58-5.mol

Synonyms:(1S)-(-)-10-Mercaptoisoborneol;(1S)-(-)-10-Mercaptoborneol;71242-58-5;7,7-dimethyl-1-(sulfanylmethyl)bicyclo[2.2.1]heptan-2-ol;71242-59-6;SCHEMBL6973112;DTXSID10541393;M1341;(1S,2R,4R)-7,7-DIMETHYL-1-(SULFANYLMETHYL)BICYCLO[2.2.1]HEPTAN-2-OL

Chemical Property of (1S)-(-)-10-Mercaptoborneol

Chemical Property:

• Melting Point: 72 °C
• Refractive Index: 1.543
• PSA: 59.03000
• LogP: 2.10340
• Solubility.: almost transparency in Chloroform
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 186.10783637
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

97% ^*data from raw suppliers

(1S)-(-)-10-Mercaptoisoborneol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(C2)O)CS)C

Technology Process of (1S)-(-)-10-Mercaptoborneol

There total 13 articles about (1S)-(-)-10-Mercaptoborneol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(1S,2S,6R,7R)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one (129887-42-9) → (1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) + bis-{(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethyl}disulfide (116195-09-6) + (2R,6S)-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one (115269-21-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; tert-butyl alcohol; for 0.166667h; Yields of byproduct given; Ambient temperature;

Reference yield: 98.0%

(+)-(1R,RS)-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 (129887-41-8) → (3aS,4R,7S,7aR)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one (95340-88-8) + (1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) + bis-{(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethyl}disulfide (116195-09-6)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; tert-butyl alcohol; for 0.166667h; Yields of byproduct given; Ambient temperature;

Reference yield: 69.0%

(1S,4R)-camphor-10-thiol (54984-43-9,77026-99-4) → (1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃; for 1.5h;

DOI:10.1021/acs.orglett.8b02528

upstream raw materials:

camphorsulfonyl chloride

Camphorsulfonyl chloride

(+)-(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

(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

Downstream raw materials:

(R,R)-trans-stilbene epoxide

(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

(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

α-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylthio)-N-phenylsuccinimide