(1R)-(+)-2,10-Camphorsultam

Base Information

• Chemical Name: (1R)-(+)-2,10-Camphorsultam
• CAS No.: 108448-77-7
• Molecular Formula: C10H17NO2S
• Molecular Weight: 215.316
• Hs Code.: 29242990
• European Community (EC) Number: 626-448-2,628-426-8
• DSSTox Substance ID: DTXSID40910735
• Nikkaji Number: J382.973A,J734.685I
• Wikidata: Q15410857,Q72451077
• Mol file: 108448-77-7.mol

Synonyms:108448-77-7;(2S)-Bornane-10,2-sultam;(+)-10,2-Camphorsultam;(1R)-(+)-2,10-Camphorsultam;MFCD00151762;(3aR,6S,7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide;(1R)-(+)-2,10,Camphorsultam;L-2,10-Camphorsultam;(+)-exo-10,2-Bornanesultam;94594-90-8;(1R)-(+)-Camphorsultam;SCHEMBL4147091;DTXSID40910735;DPJYJNYYDJOJNO-NRPADANISA-N;BCP06365;FD1226;(+)-10,2-CAMPHORSULTAM?;AKOS016842377;CS-W002434;(1R,2S)-(+)-10,2-Camphorsultam;(1R,5S)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide;(1R)-(+)-2,10-Camphorsultam, 98%;AM20120715;EN300-1177730;Q15410857;(1R,5S,7S)-10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.0,1,5]decane-3,3-dione;1932472-17-7;3H-3a,6-Methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-, 2,2-dioxide, (3aR,6S,7aS)-

Chemical Property of (1R)-(+)-2,10-Camphorsultam

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000239mmHg at 25°C
• Melting Point: 185-187 °C(lit.)
• Refractive Index: 31 ° (C=1, CHCl3)
• Boiling Point: 324.8 °C at 760 mmHg
• PKA: 11.05±0.40(Predicted)
• Flash Point: 150.3 °C
• PSA: 54.55000
• Density: 1.28 g/cm³
• LogP: 2.52390
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in Chloroform
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 215.09799996
• Heavy Atom Count: 14
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

(1R)-(+)-2,10-Camphorsultam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC13CS(=O)(=O)NC3C2)C
• Isomeric SMILES: CC1([C@H]2CC[C@@]13CS(=O)(=O)N[C@H]3C2)C
• Uses: (1R)-(+)-2,10-Camphorsultam has been used as a reactant in the synthesis of pyrrolidine acid analogs as potent dual PPARα/γ agonists.

Technology Process of (1R)-(+)-2,10-Camphorsultam

There total 48 articles about (1R)-(+)-2,10-Camphorsultam 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%

(2R,3R,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-phenethyl-pyrrolidine-3-carboxylic acid methyl ester (909191-06-6) → (+)-camphorsultam (108448-77-7,124224-04-0)

Guidance literature:

With n-butyllithium; C₈H₁₇SH; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ol061113b

Reference yield: 97.0%

(3R,3aS,4S,7R,7aR)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one (196303-41-0) → (+)-camphorsultam (108448-77-7,124224-04-0) + (3R,3aR,4S,7R,7aR)-3-Hydroxymethyl-2,3,3a,4,7,7a-hexahydro-1H-4,7-methano-inden-1-ol (196303-32-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/ja970901g

Reference yield: 92.0%

(E)-(R)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,4-dimethyl-hept-4-en-1-one (193416-18-1) → (+)-camphorsultam (108448-77-7,124224-04-0) + (2R,4E)-2,4-dimethylhept-4-en-1-ol (174393-36-3)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; 1.) - 78 deg C, 30 min, 2.) - 78 deg C - room temperature, 30 min, 3.) room temperature, 15 min;

DOI:10.1016/S0040-4020(97)00617-0

upstream raw materials:

DL camphor-10-thiazine dioxide

styrene

(2S,2'S)-N-(2',3',4',5'-tetrahydro-1'-oxido-1'-pyridinio-2'-carbonyl)bornane-10,2-sultam

ethanol

Downstream raw materials:

(2R)-N-{N-[bis(methylthio)methylidene]glycyl}bornane-10,2-sultam

N-{E-3-[dimethyl(phenyl)silyl]propenoyl}-(7R)-2,10-camphorsultam

(E)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-hydroxy-3-methoxy-phenyl)-propenone

(2R,3R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-5-oxo-pentanoic acid dibenzylamide

Refernces

• 1、 Sandoval, David,Samoshin, Andrey V.,Read De Alaniz, Javier. "Asymmetric Electrophilic α-Amination of Silyl Enol Ether Derivatives via the Nitrosocarbonyl Hetero-ene Reaction". . p. 4514 - 4517. Retrieved 2015.
• 2、 Kotian, Pravin L.,Lin, Tsu-Hsing,El-Kattan, Yahya,Chand, Pooran. "A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition". . p. 193 - 197. Retrieved 2012/12/24.