(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride

Base Information

• Chemical Name: (1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride
• CAS No.: 104530-16-7
• Molecular Formula: C₁₀H₁₃ClO₃
• Molecular Weight: 216.664
• Hs Code.: 2932209090
• European Community (EC) Number: 254-552-4,621-311-3
• Nikkaji Number: J2.699.666J
• Mol file: 104530-16-7.mol

Synonyms:(1R)-(+)-Camphanic chloride;(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride;Camphanoyl chloride;(+)-(1r,4s)-camphanic acid chloride;C10H13ClO3;(1R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride;(1s)-()-camphanic chloride;2-Oxabicyclo[2.2.1]heptane-1-carbonyl chloride, 4,7,7-trimethyl-3-oxo-, (1S,4R)-;39637-74-6;D93327;J-001191;(1R)-(+)-Camphanic chloride, for chiral derivatization, >=97.0%;3-Oxo-4beta,7,7-trimethyl-2-oxabicyclo[2.2.1]heptane-1beta-carboxylic acid chloride

Chemical Property of (1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride

Chemical Property:

• Vapor Pressure: 0.00119mmHg at 25°C
• Melting Point: 67-70 °C
• Refractive Index: 1.52
• Boiling Point: 299.5 °C at 760 mmHg
• Flash Point: 125 °C
• PSA: 43.37000
• Density: 1.298 g/cm³
• LogP: 1.87370
• Storage Temp.: −20°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 216.0553220
• Heavy Atom Count: 14
• Complexity: 336

Purity/Quality:

98% or more ^*data from raw suppliers

(+)-CAMPHANIC ACID CHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xn
• Hazard Codes: C,Xn
• Statements: 34-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2(CCC1(OC2=O)C(=O)Cl)C)C
• Isomeric SMILES: C[C@]12CC[C@](C1(C)C)(OC2=O)C(=O)Cl

Technology Process of (1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride

There total 6 articles about (1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride 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: 94.0%

(-)-camphanic acid (67111-66-4,13429-83-9) → (-)-ω-camphanic acid chloride (39637-74-6,49620-91-9,104530-16-7)

Guidance literature:

With thionyl chloride; for 3h; Heating;

Reference yield:

(1R, 4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid → (-)-camphanic acid chloride (39637-74-6,104530-16-7)

Guidance literature:

With thionyl chloride; at 60 ℃; for 3h;

DOI:10.1002/ardp.19963290104

Reference yield:

1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride (48138-74-5) → (-)-ω-camphanic acid chloride (39637-74-6,49620-91-9,104530-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: Br₂ / 23 h / 65 °C

2: water / 2 h / temp. below 30 deg C

3: 68 percent / 1.) Na₂CO₃, 2.) conc. hydrochloric acid / H₂O / 3.5 h / Heating

4: 94 percent / thionyl chloride / 3 h / Heating

With hydrogenchloride; thionyl chloride; water; bromine; sodium carbonate; In water;

upstream raw materials:

(-)-camphanic acid

1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride

1-Bromo-5,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane-2,4-dione

(+)-camphoric acid

Downstream raw materials:

cis-2-(diphenylmethyl)-1-azabicyclo<2.2.2>octan-3-yl camphanate

cis-2-(diphenylmethyl)-1-azabicyclo<2.2.2>octan-3-yl camphanate

1D-2,3,5,6-Tetra-O-benzyl-1,4-di-O-<(+)-ω-camphanoyl>-myo-inositol

C₅₄H₆₀O₁₂

Refernces

• 1、 Wanner, Klaus Th.,Praschak, Ilona,Hoefner, Georg,Beer, Herbert. "Asymmetric synthesis and enantiospecificity of binding of 2-(1,2,3,4-tetrahydro-1-isoquinolyl)-ethanol derivatives to μ and κ receptors". . p. 11 - 22. Retrieved 2007/10/02.