40724-67-2 Usage
Description
(S)-(+)-Ketopinic acid, also known as (1S)-(+)-Ketopinic acid, is a chiral ketone with a unique molecular structure that plays a significant role in various chemical reactions and applications. It is characterized by its asymmetric carbon atom, which provides it with distinct stereochemistry, making it a valuable compound in the field of organic chemistry.
Uses
Used in Pharmaceutical Industry:
(S)-(+)-Ketopinic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its chiral nature allows for the creation of enantiomerically pure products, which is crucial for the development of effective and safe medications.
Used in Chiral Ligands Synthesis:
(S)-(+)-Ketopinic acid is used as a starting material for the preparation of chiral phosphine-oxazoline ligands. These ligands are essential in asymmetric palladium-catalyzed Heck reactions of aryl or alkenyl triflates with cyclic alkenes, which are important for the synthesis of complex organic molecules with potential applications in various industries.
Used in Catalysts for Asymmetric Reactions:
(S)-(+)-Ketopinic acid is used in the synthesis of chiral imino-phosphine ligands, which are crucial for palladium-catalyzed asymmetric Diels-Alder reactions. These reactions are employed to prepare six-membered carbocycles, which are vital components in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Copper-Catalyzed Henry (Nitro Aldol) Reactions:
(S)-(+)-Ketopinic acid is also used in the preparation of chiral iminopyridine ligands, which are employed in copper-catalyzed Henry (nitro aldol) reactions between nitromethane and o-anisol. This reaction is an essential step in the synthesis of β-hydroxynitroalkanes, which are valuable building blocks for the development of various pharmaceuticals and other organic compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 40724-67-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,7,2 and 4 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 40724-67:
(7*4)+(6*0)+(5*7)+(4*2)+(3*4)+(2*6)+(1*7)=102
102 % 10 = 2
So 40724-67-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O3/c1-9(2)6-3-4-10(9,8(12)13)7(11)5-6/h6H,3-5H2,1-2H3,(H,12,13)/t6-,10+/m1/s1
40724-67-2Relevant articles and documents
Synthesis of (+)-(1S,4R)-1-(1-chlorovinyl)-7,7-dimethyl-bicyclo[2.2.1] heptan-2-one
Vostrikov,Vasikov,Spirikhin,Miftakhov
, p. 1371 - 1372 (2004)
-
Novel O-acylated amidoximes and substituted 1,2,4-oxadiazoles synthesised from (+)-ketopinic acid possessing potent virus-inhibiting activity against phylogenetically distinct influenza A viruses
Borisevich, Sophia S.,Chernyshov, Vladimir V.,Esaulkova, Iana L.,Popadyuk, Irina I.,Salakhutdinov, Nariman F.,Sinegubova, Ekaterina,Yarovaya, Olga I.,Zarubaev, Vladimir V.
, (2021/12/16)
This article describes the synthesis and antiviral activity evaluation of new substituted 1,2,4-oxadiazoles containing a bicyclic substituent at position 5 of the heterocycle and O-acylated amidoximes as precursors for their synthesis. New compounds were
Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones
Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.
, p. 12951 - 12964 (2018/11/30)
The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.
Synthesis of novel chiral Schiff bases and their application in asymmetric transfer hydrogenation of prochiral ketones
Zhou, Zhongqiang,Bian, Yongjun
scheme or table, p. 682 - 687 (2010/11/04)
Novel chiral Schiff bases were synthesized from (+)-camphor, and their application to asymmetric transfer hydrogenation of prochiral ketones is described. The asymmetric transfer hydrogenation reaction could afford excellent conversion rates (up to 97.3%) and up to 27.3% enantiomeric excess.
