63492-82-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drug molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, (S)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID METHYL ESTER is used as a precursor in the synthesis of various agrochemicals, contributing to the creation of organic compounds for agricultural applications.
Used in Organic Synthesis:
(S)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID METHYL ESTER is utilized as a versatile intermediate in organic synthesis, playing a crucial role in the formation of a wide range of organic compounds.
Used in Drug Development:
As a compound with potential pharmacological properties, (S)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID METHYL ESTER is used in drug development for its sedative effects and potential anti-inflammatory actions, indicating its use in the creation of therapeutic agents.

InChI:InChI=1/C11H13NO2/c1-14-11(13)10-7-6-8-4-2-3-5-9(8)12-10/h2-5,10,12H,6-7H2,1H3/t10-/m0/s1

Upstream product

• 63430-79-5 1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester 
• 71-36-3 butan-1-ol 
• 19575-07-6 quinoline-2-carboxylic acid methyl ester 
• 78348-26-2 1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester hydrochloride 
• 1300730-72-6 2-(2-(2-hydroxyethyl)phenyl)isoindoline-1,3-dione 
• 5339-85-5 2-aminophenethyl alcohol 
• 67-56-1 methanol 
• 92976-98-2 1,2,3,4-tetrahydroquinolic acid 
• 93-10-7 quinoline-2-carboxylic acid 
• 46185-24-4 1,2,3,4-tetrahydroquinoline-2-carboxylic acid 

Downstream Products

• 898533-05-6 (S)-(-)-N-(4-(4-m-tolylpiperazin-1-yl)butyl)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 75493-94-6 (S)-(-)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 898533-02-3 (S)-(-)-N-(4-(4-m-tolylpiperazin-1-yl)butyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 898533-27-2 (S)-(-)-N-[4-(4-phenylpiperazin-1-yl)butyl]-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 1294477-80-7 (S)-2,4,6-trimethyl-N-((1,2,3,4-tetrahydroquinolin-2-yl)methyl)benzenamine 
• 1294477-79-4 (S)-N-mesityl-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 1294477-78-3 (S)-allyl 2-(mesitylcarbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate 
• 157521-46-5 2-methyl (S)-(-)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylate 

Relevant academic research and scientific papers

Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction

Biomimetic asymmetric reduction of 2-functionalized quinolines has been successfully developed with the chiral and regenerable NAD(P)H model CYNAM in the presence of transfer catalyst simple achiral phosphoric acids, providing the chiral 2-functionalized

Multikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 1. Manufacture of the Acid Moiety and Development of Some Key Reactions

Our efforts toward the process development of drug candidate 1 are described in a series of two papers. This manuscript focuses on the synthesis of kilogram quantities of acid precursor 2 to provide batches of material for preclinical studies and first-in

P -Chiral, N -phosphoryl sulfonamide Br?nsted acids with an intramolecular hydrogen bond interaction that modulates organocatalysis

Br?nsted acids exemplified by OttoPhosa I (5c) were designed and evaluated in the asymmetric transfer hydrogenation of quinolines. Their catalytic properties are modulated by an intramolecular hydrogen bond that rigidifies their catalytic cavity, accelerates the reaction rate and improves enantioselectivity.

B(C6F5)3-catalyzed metal-free hydrogenations of 2-quinolinecarboxylates

A metal-free hydrogenation of 2-quinolinecarboxylates has been realized by using 5 mol% of B(C6F5)3 as catalyst. A variety of tetrahydroquinolines were obtained in 57–99% yields. An attempt for the asymmetric hydrogenation with chiral boron Lewis acids generated from chiral dienes afforded very low ee's.

Enantioselective Copper-Catalyzed Intramolecular N?H Bond Insertion: Synthesis of Chiral 2-Carboxytetrahydroquinolines

The first highly enantioselective intramolecular N?H bond insertion was realized by using copper catalysts modified with chiral spirobisoxazoline ligands, which provides a novel strategy for the synthesis of chiral 2-carboxytetrahydroquinolines. This reaction features fast reaction rate, high yield, high enantioselectivity, and mild reaction conditions. (Figure presented.).

Asymmetric synthesis of chiral heterocyclic amino acids via the alkylation of the Ni(II) complex of glycine and alkyl halides

An investigation into the reactivity profile of alkyl halides has led to the development of a new method for the asymmetric synthesis of chiral heterocyclic amino acids. This protocol involves the asymmetric alkylation of the Ni(II) complex of glycine to form an intermediate, which then decomposes to form a series of valuable chiral amino acids in high yields and with excellent diastereoselectivity. The chiral amino acids underwent a smooth intramolecular cyclization process to afford the valuable chiral heterocyclic amino acids in high yields and enantioselectivities. This result paves the way for the development of a new synthetic method for chiral heterocyclic amino acids.

Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines

The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.

Highly enantioselective hydrogenation of new 2-functionalized quinoline derivatives

The asymmetric hydrogenation of a new series of 2-functionalized quinolines has been developed in the presence of in situ generated catalysts obtained from [Ir(cod)Cl]2/(R)-bisphosphine/I2 combinations. The enantioselectivity levels

A novel ligand for the enantioselective ruthenium-catalyzed olefin metathesis

A bridge connects and efficiently transfers the chirality from the backbone of a N-heterocyclic carbene (NHC) to the metal center. The result is excellent enantioselectivities in the ruthenium-catalyzed, asymmetric ring-opening cross-metathesis of norborn

Stereoselective synthesis of optically active cyclic α- And β-amino esters through lipase-catalyzed transesterification or interesterification processes

A series of cyclic α- and β-amino esters belonging to a family of indolines and quinolines have been efficiently synthesized to study their behavior in lipase-mediated kinetic resolution reactions. The influence of the fused ring structure to the benzene ring and the position of the ester functionality relative to the amino group have been demonstrated, finding excellent values of enantiodiscrimination in the transesterification reaction of methyl indoline-3-carboxylate with n-butanol catalyzed by Candida antarctica lipase B being observed. On the other hand, low to moderate selectivities have been found when using a wide panel of lipases toward methyl indoline-2- carboxylate or 1,2,3,4-tetrahydroquinoline derivatives in alkoxycarbonylation, transesterification or interesterification reactions.