(1S)-10-Camphorsulfonamide

Base Information

• Chemical Name: (1S)-10-Camphorsulfonamide
• CAS No.: 60933-63-3
• Molecular Formula: C10H17NO3S
• Molecular Weight: 231.316
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID80350252
• Nikkaji Number: J730.109J
• Wikidata: Q82126091
• Mol file: 60933-63-3.mol

Synonyms:(1S)-10-Camphorsulfonamide;60933-63-3;(1S)-(+)-10-Camphorsulfonamide;[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide;((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonamide;[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonamide;SCHEMBL2385301;DTXSID80350252;(1S)-10-Camphorsulfonamide, 96%;EN300-19631959;Bicyclo[2.2.1]heptane-1-methanesulfonamide,7,7-dimethyl-2-oxo-,(1S,4R)-;1-[(1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonamide

Chemical Property of (1S)-10-Camphorsulfonamide

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 5.48E-06mmHg at 25°C
• Melting Point: 129-132 °C(lit.)
• Refractive Index: 1.541
• Boiling Point: 380.4°C at 760 mmHg
• PKA: 10.14±0.60(Predicted)
• Flash Point: 183.8°C
• PSA: 85.61000
• Density: 1.28 g/cm³
• LogP: 2.45140
• Solubility.: Dichloromethane
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 231.09291458
• Heavy Atom Count: 15
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

(1S)-(+)-10-Camphorsulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(=O)C2)CS(=O)(=O)N)C
• Isomeric SMILES: CC1([C@@H]2CC[C@]1(C(=O)C2)CS(=O)(=O)N)C
• Uses: (1S)-(+)-10-Camphorsulfonamide is a useful synthetic intermediate. Used for asymmetric hydroxylation An amino chiral derivative of Camphor An amino chiral derivative of Camphor.

Technology Process of (1S)-10-Camphorsulfonamide

There total 12 articles about (1S)-10-Camphorsulfonamide 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: 98.0%

(1S)-(+)-camphor-10-sulfonyl azide → (1S)-10-camphorsulfonamide (60933-63-3)

Guidance literature:

With hydrogen; In ethanol; at 20 ℃; for 2h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2019.02.035

Reference yield: 90.0%

Camphorsulfonyl chloride (21286-54-4) → (1S)-10-camphorsulfonamide (60933-63-3)

Guidance literature:

With ammonium hydroxide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja00233a025

Reference yield: 12.0%

(2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (1S)-10-camphorsulfonamide (60933-63-3) + (1S)-(-)-camphorsulfonylimine (60886-80-8)

Guidance literature:

With lithium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1246/bcsj.73.423

upstream raw materials:

(+)-(1S)-Campher-10-sulfonsaeure-chlorid

((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride

Camphorsulfonyl chloride

(2R)-bornane-10,2-sultam

Downstream raw materials:

N-(3-nitrobenzylidene)-d-10-camphorsulfonamide

N-(2-nitrobenzylidene)-d-10-camphorsulfonamide

acrylcamphorsultam

(1S)-N-crotyl-2,10-camphorsultam

Refernces

• 1、 Pia?tek, Anna,Chapuis, Christian. "Influence of norbornanone substituents on both the Wagner-Meerwein skeletal rearrangements under sulfonation conditions and the diastereoselectivity of the corresponding N,N′-bis-fumaroyl sultams in uncatalyzed Diels-Alder cycloadditions to cyclopenta-1,3-diene". . p. 4247 - 4249. Retrieved 2013/07/26.
• 2、 Hasegawa, Tomoyuki,Yamamoto, Hisashi. "A practical synthesis of optically active (R)-2-propyloctanoic acid: Therapeutic agent for Alzheimer's disease". . p. 423 - 428. Retrieved 2007/10/03.