THIOCINEOLE

Base Information

• Chemical Name: THIOCINEOLE
• CAS No.: 5718-75-2
• Molecular Formula: C10H18S
• Molecular Weight: 170.319
• Mol file: 5718-75-2.mol

Synonyms:6-Thiabicyclo[3.2.1]octane,4,7,7-trimethyl-, exo-(-)-;p-Menthane, 2,8-epithio- (7CI,8CI);exo-(-)-4,7,7-Trimethyl-6-thiabicyclo(3.2.1)octane;

Chemical Property of THIOCINEOLE

Chemical Property:

• Vapor Pressure: 0.149mmHg at 25°C
• Refractive Index: 1.492
• Boiling Point: 222.7 °C at 760 mmHg
• Flash Point: 79 °C
• PSA: 25.30000
• Density: 0.941 g/cm³
• LogP: 3.46070
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R,4R,5R)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of THIOCINEOLE

There total 15 articles about THIOCINEOLE 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: 76.5%

C10H18S (83150-77-0,83150-78-1) → (1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane (5718-75-2)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 3h; Inert atmosphere; Reflux;

Reference yield: 61.0%

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane (5718-75-2) + (1R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]oct-3-ene (1208985-44-7)

Guidance literature:

With crithmene; sulfur; at 125 ℃; for 24h; enantioselective reaction;

DOI:10.1021/ja405073w

Reference yield: 57.0%

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane (5718-75-2)

Guidance literature:

With sulfur; crithmene; In neat (no solvent); at 125 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0037-1609580

upstream raw materials:

D-limonene

(1R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]oct-3-ene

limonene.

(-)-(S)-α-terpineol

Downstream raw materials:

(1R,4R,5R,6R)-6-benzyl-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octan-6-ium trifluoromethanesulfonate

4-((((1R,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexyl)thio)methyl)benzonitrile

Refernces

• 1、 Fearraigh, Martin P. ó,Matlock, Johnathan V.,Illa, Ona,McGarrigle, Eoghan M.,Aggarwal, Varinder K.. "Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination". . p. 3337 - 3343. Retrieved 2018/09/04.
• 2、 Illa, Ona,Arshad, Muhammad,Ros, Abel,McGarrigle, Eoghan M.,Aggarwal, Varinder K.. "Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine". supporting information; experimental part. p. 1828 - 1830. Retrieved 2010/04/25.