(1s,4r)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid

Base Information

• Chemical Name: (1s,4r)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid
• CAS No.: 40724-67-2
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.219
• Hs Code.: 2918300090
• European Community (EC) Number: 625-243-5
• Nikkaji Number: J89.375G
• Mol file: 40724-67-2.mol

Synonyms:(+)-Ketopinic acid;(1S)-(+)-Ketopinic acid;40724-67-2;(1s,4r)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid;(S)-(+)-Ketopinic Acid;Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-, (1S,4R)-;S-(+)-ketopinic acid;(1S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid;AK-88562;(S)-(+)-KetopinicAcid;SCHEMBL21458724;(1S,4R)-7,7-Dimethyl-2-oxo-norbornane-1-carboxylic acid;MFCD08061242;(1S)-(+)-Ketopinic acid, 99%;AKOS006282096;CCG-208411;CS-W017111;BP-12916;DS-18484;EN300-365565;A825258;SR-05000002262;SR-05000002262-2

Chemical Property of (1s,4r)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.000109mmHg at 25°C
• Melting Point: 237-239 ºC
• Refractive Index: 25.5 ° (C=0.65, MeOH)
• Boiling Point: 313.3 °C at 760 mmHg
• PKA: 3.67±0.40(Predicted)
• Flash Point: 157.5 °C
• PSA: 54.37000
• Density: 1.238 g/cm³
• LogP: 1.46640
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 293

Purity/Quality:

98% ^*data from raw suppliers

7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(=O)C2)C(=O)O)C
• Isomeric SMILES: CC1([C@@H]2CC[C@]1(C(=O)C2)C(=O)O)C
• Uses: (1S)-(+)-Ketopinic acid may be used to prepare:Chiral phosphine-oxazoline ligands, which can used in asymmetric palladium-catalyzed Heck reaction of aryl or alkenyl triflates with cyclic alkenes.A chiral imino-phosphine ligand, which can be used in palladium-catalyzed asymmetric Diels–Alder reactions to prepare six-membered carbocycles.A chiral iminopyridine ligand, which can be used in copper-catalyzed Henry (nitro aldol) reaction between nitromethane and o-anisol to form the corresponding β-hydroxynitroalkane.

Technology Process of (1s,4r)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid

There total 20 articles about (1s,4r)-7,7-Dimethyl-2-oxobicyclo[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: 95.0%

(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid methylester (125637-45-8) → (1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2)

Guidance literature:

Alkaline hydrolysis;

DOI:10.1007/s11178-005-0022-4

Reference yield: 90.0%

(1S)-10-camphorsulfonic acid (3144-16-9,61380-66-3) → (1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2)

Guidance literature:

(1S)-10-camphorsulfonic acid; With thionyl chloride; for 1.5h; Reflux;

With potassium permanganate; potassium carbonate; In water monomer; acetonitrile; at 70 - 80 ℃; for 48h;

With anhydrous potassium sulfite; sulfuric acid;

DOI:10.1016/j.bmcl.2021.128465

Reference yield: 87.0%

Camphorsulfonyl chloride (21286-54-4) → (1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2)

Guidance literature:

With potassium permanganate; sodium carbonate; In water; acetonitrile; at 20 - 70 ℃; for 1.5h;

DOI:10.1021/acs.joc.8b00655

upstream raw materials:

7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbaldehyde

(1R,4R)-1-hydroxymethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one

Camphorsulfonyl chloride

(1S)-10-camphorsulfonic acid

Downstream raw materials:

(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride

ketopinic acid chloride

2-Hydroxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carboxylic acid

(1R)-7,7-dimethyl-1-phenylbicyclo<2.2.1>heptan-2-one

Refernces

• 1、 Wang, Ying-Chuan,Lu, Tzung-Min,Elango, Shanmugham,Lin, Chao-Kuo,Tsai, Chia-Tzung,Yan, Tu-Hsin. "Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles". . p. 691 - 695. Retrieved 2002.
• 2、 Dalinger, Alexander I.,Kalinin, Mikhail A.,Kuranov, Sergey O.,Munkuev, Aldar A.,Okhina, Alina A.,Ottenbacher, Roman V.,Patrusheva, Oxana S.,Ponomarev, Konstantin Y.,Rogachev, Artem D.,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Vatsadze, Sergey Z.,Volcho, Konstantin P.. "Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones". . . Retrieved 2021/12/20.
• 3、 -. "NOVEL ARYLATED CAMPHENES, PROCESSES FOR THEIR PREPARATION AND USES THEREOF". Page/Page column 34. . Retrieved 2011/06/19.