(1S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid

Base Information

• Chemical Name: (1S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
• CAS No.: 13429-83-9
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Hs Code.: 29329995
• European Community (EC) Number: 236-552-6
• Mol file: 13429-83-9.mol

Synonyms:13429-83-9;(1S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid;(1S)-(-)-Camphanic acid;(-)-Camphanic acid;SCHEMBL223631;AKOS015892631;CS-W010541

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

Chemical Property:

• Appearance/Colour: white to slightly beige crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 201-205 °C
• Refractive Index: 1.532
• Boiling Point: 355.489°C at 760 mmHg
• PKA: 3.36±0.60(Predicted)
• Flash Point: 142.124°C
• PSA: 63.60000
• Density: 1.296 g/cm³
• LogP: 1.19290
• Storage Temp.: Store below +30°C.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 198.08920892
• Heavy Atom Count: 14
• Complexity: 333

Purity/Quality:

97% ^*data from raw suppliers

(S)-CamphanicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-37/39-26-36-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2(CCC1(OC2=O)C(=O)O)C)C
• Isomeric SMILES: CC1([C@@]2(CCC1(C(=O)O2)C)C(=O)O)C
• Uses: (1S)-(-)-Camphanic acid may be used in the preparation of (-)-(1S,4R)-camphanoyl chloride by reacting with thionyl chloride.

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

There total 14 articles about (1S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid 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: 96.0%

(3R)-3-Camphanoyloxy-4-oxo-9-vinyl-β-jonol → (-)-camphanic acid (67111-66-4,13429-83-9) + (3R)-3-Hydroxy-4-oxo-9-vinyl-β-jonol

Guidance literature:

With sodium hydroxide; In methanol; for 0.166667h;

DOI:10.1002/hlca.19810640750

Reference yield: 91.0%

(-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-82-3) → ((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol (432036-83-4) + (-)-camphanic acid (67111-66-4,13429-83-9)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 - 25 ℃; for 1h; Large scale;

DOI:10.1021/op3003085

Reference yield: 87.0%

(-)-(1R,3R)-3-chlorocamphoric anhydride (87859-84-5) → (-)-camphanic acid (67111-66-4,13429-83-9)

Guidance literature:

With sulfuric acid; Heating;

upstream raw materials:

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

(1R,2R,4R)-2-exo-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl(1S)-camphanate

(-)-(1R,3R)-3-chlorocamphoric anhydride

(1S)-(-)-camphanic chloride

Downstream raw materials:

(R)-Methoxy-phenyl-acetic acid (4bR,8aR,9R)-7-[1-ethoxycarbonyl-meth-(E)-ylidene]-2-methoxy-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-9-yl ester

4'-N-camphanyl-(4'R)-<4-2H1>-3,5'-O-dibenzylpyridoxamine

4'-N-camphanyl-(4'S)-<4-2H1>-3,5'-O-dibenzylpyridoxamine

(4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl camphanate