104530-16-7

Basic information

• Product Name: (+)-CAMPHANIC ACID CHLORIDE
• Synonyms: (S)-(-)-camphanoyl chloride;SALOR-INTL300764;(+)-CAMPHANIC ACID CHLORIDE;(-)-camphanoyl chloride;(1R)-(+)-CAMPHANIC CHLORIDE;(1R)-(+)-CAMPHANOYL CHLORIDE;(1R)-4,7,7-TRIMETHYL-3-OXO-2-OXABICYCLO[2.2.1]HEPTANE-1-CARBONYL CHLORIDE;(1R)-3-OXO-4,7,7-TRIMETHYL-2-OXABICYCLO[2.2.1]HEPTANE-1-CARBOXYL CHLORIDE
• CAS NO: 104530-16-7
• Molecular Formula: C₁₀H₁₃ClO₃
• Molecular Weight: 216.66
• EINECS: 254-552-4
• Product Categories: Chiral Compound
• Mol File: 104530-16-7.mol

Chemical Properties

• Melting Point: 67-70 °C
• Boiling Point: 299.5 °C at 760 mmHg
• Flash Point: 125 °C
• Appearance: /
• Density: 1.298 g/cm³
• Vapor Pressure: 0.00119mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: −20°C
• CAS DataBase Reference: (+)-CAMPHANIC ACID CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CAMPHANIC ACID CHLORIDE(104530-16-7)
• EPA Substance Registry System: (+)-CAMPHANIC ACID CHLORIDE(104530-16-7)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 104530-16-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Camphanic acid chloride is used as a key intermediate in the synthesis of pharmaceuticals due to its reactivity and capacity to form various chemical bonds, contributing to the development of new drugs and medicinal compounds.
Used in Organic Synthesis:
(+)-Camphanic acid chloride serves as a catalyst and reagent in organic synthesis, facilitating the formation of desired products and enhancing the efficiency of chemical reactions in the preparation of organic compounds.
Used in Asymmetric Synthesis:
(+)-Camphanic acid chloride is utilized as a valuable tool in asymmetric synthesis, enabling the preparation of complex molecules with specific stereochemistry, which is crucial for the production of enantiomerically pure compounds in various applications, including pharmaceuticals and agrochemicals.
Used in the Preparation of Optically Active Compounds:
As a chiral molecule, (+)-Camphanic acid chloride is used in the preparation of optically active compounds, which are important in various fields such as pharmaceuticals, where the stereochemistry of a molecule can significantly affect its biological activity and efficacy.

InChI:InChI=1/C10H13ClO3/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3/t9-,10-/m1/s1

Upstream product

• 124-83-4 (+)-camphoric acid 
• 10333-96-7 1-Bromo-5,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane-2,4-dione 
• 48138-74-5 1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride 
• 67111-66-4 (-)-camphanic acid 

Downstream Products

• 119874-36-1 1-O-(tert-butyldiphenylsilyl)-4-O-camphanyl-2,3:5,6-di-O-isopropylidene-D-myo-inositol 
• 119874-36-1 3-O-(tert-butyldiphenylsilyl)-6-O-camphanyl-1,2:4,5-di-O-isopropylidene-D-myo-inositol 
• 131147-10-9 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aR,4R,5S,6R,7R,7aR)-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 131147-10-9 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5R,6S,7S,7aS)-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 131146-82-2 C₅₄H₆₀O₁₂ 
• 131146-82-2 C₅₄H₆₀O₁₂ 
• 131147-17-6 C₅₄H₆₀O₁₂ 
• 131147-17-6 C₅₄H₆₀O₁₂ 
• 113299-39-1 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid 1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-2-(4-fluoro-phenylsulfanyl)-1-methyl-ethyl ester 
• 114218-18-7 1D-2,3,6-Tri-O-benzyl-4,5-O-isopropylidene-myo-inositol (+)-ω-camphanate 
• 114218-18-7 (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 132662-61-4 (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2S,3S,4R,5R,6S)-2,3,4,6-tetrakis-benzyloxy-5-hydroxy-cyclohexyl ester 
• 132662-61-4 (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxy-cyclohexyl ester 
• 134039-22-8 (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester 

Relevant articles and documents

6-Acylamino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3-diones mechanism-based inhibitors of human leukocyte elastase and cathepsin G: Effect of chirality in the 6-acylamino substituent on inhibitory potency and selectivity

Inhibition of human leukocyte elastase(HLE) by a series of 6-acylamino-2-[(ethylsulfonyl)oxy)]-1H-isoindole-1,3-diones was determined and compared to their inhibition of ChT, PPE, and Cat G. The best inhibitor of the series was 6-((1′S)-camphanyl)amino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3-dione 5b, with a kobs/[I]=11,000M-1 s-1. This study revealed that HLE shows a preference for the S stereochemistry and tolerates hydrophobic substituents in the Sn′ binding sites. Molecular modeling of noncovalent HLE-inhibitor complexes was used as a tool to investigate our binding model. Buffer stability assays reveal that these compounds are susceptible to hydrolysis at physiological pH. Copyright

Asymmetric synthesis and enantiospecificity of binding of 2-(1,2,3,4-tetrahydro-1-isoquinolyl)-ethanol derivatives to μ and κ receptors

A number of 2-(1,2,3,4-tetrahydro-1-isoquinolyl)-ethanol derivatives 7a-e have been synthesized in diastereomerically and enantiomerically pure form and have been evaluated for their binding affinity at μ and κ opioid receptors. The amido ketones 5a-c and ent-5a-c, which were accessible by employing 3b and ent-3b for Asymmetric Electrophilic Amidoalkylation reactions, served as starting compounds. Upon reduction of 5a-c and ent-5a-c the amido alcohols l-6a-c, u-6a-c, ent-l-6a-c and ent-u-6a-c were obtained. Hydrolysis of these compounds yielded the secondary amino alcohols l-7a-c, u-7a-c, ent-l-7a-c and ent-u-7a-c and upon reductive methylation of l-7b-c, u-7b-c, ent-l-7b-c and ent-u-7b-c with CH2O and NaCNBH3 the tertiary amino alcohols l-7d-e, u-7d-e, ent-l-7d-e and ent-u-7d-e were obtained. The binding affinities of the final compounds l-7a-e, u-7a-e, ent-l-7a-e and ent-u-7a-e at both the μ and the κ receptor were strongly dependent on their stereochemistry. In each case isomers exhibited higher affinity at the μ than at the κ receptor. For the secondary amino alcohols 7a-c the affinity at the μ receptor followed the stereochemical order l-7 > ent-l-7 > ent-u-7 > u-7 whereas for the tertiary amino alcohols the order l-7 > u-7 > ent-l-7 > ent-u-7 was found. The stereoisomers l-7d and l-7e of the tertiary amino alcohols were found to be the most active compounds the latter exhibiting a K(i) value of 7.17 which is close to that of Morphine (K(i) 1.64). In an in vivo model, the Writhing Test, both compounds l-7d and l-7e displayed high analgetic activity.

Preparation of (-)-(1S,4R)-Camphanoyl Chloride heptane-1-carbonyl Chloride, 4,7,7-Trimethyl-3-oxo, (1S)->

A convenient three step procedure for the preparation of (-)-(1S,4R)-camphanoyl chloride, starting from (+)-camphoric acid (A) via (-)-bromocamphoric anhydride (B) and (-)-camphanic acid (C) is described.