60886-80-8

Basic information

• Product Name: (1S)-(-)-CAMPHORSULFONYLIMINE
• Synonyms: (7S)-(-)-10,10-DIMETHYL-3-THIA-4-AZATRICYCLO[5.2.1.01,5]DEC-4-ENE 3,3-DIOXIDE;(7S)-10,10-DIMETHYL-3-THIA-4-AZATRICYCLO[5.2.1.01,5]DEC-4-ENE-3,3-DIOXIDE;(7S)-(-)-10,10-DIMETHYL-5-THIA-4-AZATRICYCLO[5.2.1.0(3,7)]DEC-3-ENE-5,5-DIOXIDE;(3AS)-(-)-4,5,6,7-TETRAHYDRO-8,8-DIMETHYL-3H-3A,6-METHANO-2,1-BENZISOTHIAZOLE 2,2-DIOXIDE;(3AS)-4,5,6,7-TETRAHYDRO-8,8-DIMETHYL-3H-3A,6-METHANO-2,1-BENZISOTHIAZOLE-2,2-DIOXIDE;(-)-10-CAMPHORSULFONIMINE;(1S)-(-)-CAMPHORSULFONYLIMINE;(1S)-(-)-(10-CAMPHORSULFONYL)IMINE
• CAS NO: 60886-80-8
• Molecular Formula: C₁₀H₁₅NO₂S
• Molecular Weight: 213.3
• Product Categories: Chiral Reagents;Bicyclic Monoterpenes;Biochemistry;Terpenes;Chiral Compound;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 60886-80-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 228-230 °C(lit.)
• Boiling Point: 337℃
• Flash Point: 158℃
• Appearance: White Cyrstalline Solid
• Density: 1.50
• Vapor Pressure: 0.000208mmHg at 25°C
• Refractive Index: -31 ° (C=2, CHCl3)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetone, Dichloromethane, Hot Methanol
• PKA: -1.63±0.40(Predicted)
• BRN: 85296
• CAS DataBase Reference: (1S)-(-)-CAMPHORSULFONYLIMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(-)-CAMPHORSULFONYLIMINE(60886-80-8)
• EPA Substance Registry System: (1S)-(-)-CAMPHORSULFONYLIMINE(60886-80-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 60886-80-8(Hazardous Substances Data)

Usage

Description

(1S)-(-)-CAMPHORSULFONYLIMINE, also known as (1S)-(-)-Camphor sulfonylimine, is a white crystalline solid that serves as a valuable synthetic intermediate in the field of organic chemistry. It is derived from camphor and has unique chemical properties that make it suitable for various applications, particularly in asymmetric hydroxylation reactions.

Uses

Used in Pharmaceutical Industry:
(1S)-(-)-CAMPHORSULFONYLIMINE is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its application is primarily due to its ability to facilitate asymmetric hydroxylation reactions, which are crucial in the synthesis of enantiomerically pure drugs. This process helps in creating more effective and selective medications with fewer side effects.
Used in Chemical Research:
In the field of chemical research, (1S)-(-)-CAMPHORSULFONYLIMINE is employed as a key building block for the synthesis of various complex organic molecules. Its unique reactivity and structural properties make it an essential tool in the development of novel compounds with potential applications in various industries, including materials science, agrochemicals, and pharmaceuticals.
Used in Asymmetric Hydroxylation:
(1S)-(-)-CAMPHORSULFONYLIMINE is used as a chiral auxiliary in asymmetric hydroxylation reactions. Its application is significant because it helps in achieving high enantioselectivity, which is essential for the synthesis of biologically active compounds with a single enantiomer. This selective synthesis is crucial in the development of more effective and safer drugs, as well as in the production of other chiral compounds with specific properties.

InChI:InChI=1/C10H15NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7H,3-6H2,1-2H3/t7-,10-/m1/s1

Upstream product

• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 4431-79-2 bis(benzylthio)methane 
• 6994-93-0 ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride 
• 21286-54-4 (+)-(1S)-Campher-10-sulfonsaeure-chlorid 
• 17854-63-6 (+/-)-2-oxo-bornane-10-sulfonic acid amide 
• 60933-63-3 (1S)-10-camphorsulfonamide 
• 68-12-2 N,N-dimethyl-formamide 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 213914-68-2 N-[(2S)-2-hexyl-4-pentenoyl]-(1S)-(-)-10,2-camphorsultam 
• 21286-54-4 Camphorsulfonyl chloride 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 141-52-6 sodium ethanolate 
• 67-64-1 acetone 
• 67-56-1 methanol 

Downstream Products

• 123735-35-3 (-)-<(4-exo-Benzylcamphoryl)sulfonyl>oxaziridine 
• 123735-35-3 C₁₇H₂₁NO₃S 
• 1060751-37-2 (3aS,6S,7aS)-8,8-dimethyl-7-oxo-7a-phenylethynyl-1,4,5,6,7,7a-hexahydro-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 195877-76-0 Bornane<10,2>sultam 
• 132532-68-4 (+)-<(4-exo-p-Trifluoromethylbenzylcamphoryl)sulfonyl>oxaziridine 
• 132532-69-5 (+)-<(4-exo-p-Methoxybenzylcamphoryl)sulfonyl>oxaziridine 
• 127184-05-8 (+)-((8,8-Dichlorocamphoryl)sulfonyl)oxaziridine 
• 94594-91-9 acrylcamphorsultam 
• 94668-55-0 (1S)-N-crotyl-2,10-camphorsultam 

Relevant articles and documents

(+)-camphorsulfonylimine

The norbornane ring system in the title molecule, 8, 8-dimethy 1-3, 3a, 4,5,6,7-hexahydro-3a, 6-methanobenz[c]isothiazole S,S-dioxide, C10H15NO2S, is regular with normal bond lengths and angles. The bridgehead bond angle is 92.5 (2)°. The five-membered ring of the sulfonylimine moiety adopts a flattened envelope conformation. The crystal structure is stabilized by weak C - H. . .O hydrogen bonds.

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

Compounds containing two alkyne groups in close vicinity at the rigid skeleton of camphorsulfonamide show unique reactivities when treated with electrophiles or catalytic amounts of platinum(II). The formed product structures depend not only on the reagents used but also on the substituents attached to the triple bonds. Cycloisomerisations with perfect atom economy lead to polycyclic heterocycles that resemble to some extent the AB ring system of paclitaxel. Herein, we present practical synthetic methods for the selective synthesis of precursor dialkynes bearing different substituents (alkyl, aryl) at the triple bonds, based on ketals or an imine as protecting groups. We show for isomeric dialkynes that the reaction cascade induced by Pt(II) includes ring annulation, sulphur reduction, and ring enlargement. One isomeric dialkyne additionally allows for the isolation of a pentacyclic compound lacking the ring enlargement step, which we have proposed as a potential intermediate in the catalytic cycle.

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

The Wagner-Meerwein domino rearrangement of norbornanone skeletons, under sulfonation conditions, is strongly influenced by the absence of a gem-dimethyl moiety at C(7). As a result, sulfonation at C(10) is less efficient due to a divergent pathway in the intermediate double bond formation and/or isomerization. Furthermore, the absence of such a gem-dimethyl moiety in the corresponding norbornane[10,2]sultam derivatives, sterically influences the orientation of the SO(1) and SO(2) substituents, hence on the π-facial steric shielding of the thermodynamically more stable anti-s-cis N-alkenoyl dienophiles. As a consequence, their diastereoselective [4+2] cycloadditions to cyclopenta-1,3-diene, under nonchelating conditions, are not as efficient due to a less pseudo axial SO(1) and the consequent loss of pseudo C 2-symmetry.