68965-62-8

Usage

Uses

Used in Organic Synthesis:
1-Cyclohexene-1-carboxylic acid, 2-bromoserves as a key intermediate in organic synthesis, facilitating the creation of a wide range of chemical products. Its unique structure allows for multiple reaction pathways, contributing to the diversity of synthesized compounds.
Used in Pharmaceutical Production:
1-Cyclohexene-1-carboxylic acid, 2-bromois utilized in the production of pharmaceuticals due to its potential to be incorporated into drug molecules. Its presence can influence the pharmacological properties of the final product, such as activity, selectivity, and stability.
Used in Agrochemicals:
1-Cyclohexene-1-carboxylic acid, 2-bromois also employed in the development of agrochemicals, which are chemicals used in agricultural or horticultural settings. Its role can be pivotal in enhancing crop protection products or in developing new pesticides.
Used as a Starting Material for Derivatives:
1-Cyclohexene-1-carboxylic acid, 2-bromocan be used as a starting material for the synthesis of various derivatives. This allows for the exploration of new chemical entities and the expansion of the chemical library for research and development purposes.
Involved in Chemical Reactions:
Due to its reactivity, 1-Cyclohexene-1-carboxylic acid, 2-bromocan participate in a variety of chemical reactions, such as substitution, addition, and elimination reactions. This makes it a useful tool for advancing chemical knowledge and developing new methodologies in organic chemistry.

Upstream product

• 72422-64-1 2-bromocyclohex-1-ene-1-carboxylic acid methyl ester 
• 38127-47-8 2-bromocyclohex-1-ene-1-carbaldehyde 
• 108-94-1 cyclohexanone 

Downstream Products

• 552857-10-0 2-bromo-N-phenyl-1-cyclohexene-1-carboxamide 
• 72422-64-1 2-bromocyclohex-1-ene-1-carboxylic acid methyl ester 
• 159389-47-6 2-bromo-1-cyclohexene-1-carbonyl chloride 
• 1010098-53-9 2-bromo-1-cyclohexenecarboxylic acid amide 
• 902142-51-2 (2-bromo-1-cyclohex-1-enyl)-(2,5-dimethyl-pyrrol-1-yl)-methanone 
• 857674-69-2 2-(4,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)cyclohex-1-ene-1-carboxylic acid methyl ester 
• 857674-63-6 2-(2,3,4,5-tetramethoxyphenyl)cyclohex-1-ene-1-carboxylic acid methyl ester 
• 857674-75-0 2-(2,5-dihydroxy-3,4-dimethoxyphenyl)cyclohex-1-ene-1-carboxylic acid methyl ester 
• 52850-98-3 5-methyl-7,8,9,10-tetrahydrophenanthridin-6(5H)-one 
• 552857-08-6 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide 
• 19178-21-3 2-methyl-5,6,7,8-tetrahydronquinazolin-4(3H)-one 
• 33081-07-1 2-amino-5,6,7,8-tetrahydroquinazolin-4-one 
• 34127-13-4 2-phenyl-5,6,7,8-tetrahydronquinazolin-4(3H)-one 
• 23902-01-4 2-propyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one 

Relevant academic research and scientific papers

SELECTIVE PHOSPHATASE INHIBITORS BASED ON ILLUDALIC ACID

The present disclosure provides novel selective phosphatase inhibitor compounds based on illudalic acid. The present disclosure provides a streamlined method of synthesizing illudalic acid and a method for synthesizing phosphatase inhibitor compounds. The method of this invention provides convergent benzannulation of β-keto amides and esters, followed by a one-pot reduction / hydrolysis sequence. The concise synthetic approach provided by this invention enables rapid assembly of illudalog compounds of this invention that are potent protein tyrosine phosphatase receptor-type D (PTPRD) inhibitors.

Synthesis of illudalic acid and analogous phosphatase inhibitors

Developing an efficient, concise synthesis of the fungal natural product illudalic acid has been a long-standing challenge, made more pressing by the recent discovery that illudalic acid and analogs are selective phosphatase inhibitors. Syntheses of illudalic acid have become progressively more efficient over the decades yet remain strategically grounded in a 17-step synthesis reported in 1977. Here we validate a two-step process—convergent [4 + 2] benzannulation and one-pot coordinated functional group manipulations—for preparing the key trifunctional pharmacophore of illudalic acid. The modular building blocks are readily available in 2-3 steps, for a longest linear sequence (LLS) of 5 steps to illudalic acid from 3,3-dimethylcyclopentanone. A small collection of analogous indanes and tetralins featuring the same pharmacophore were prepared by a similar route. These compounds potently and selectively inhibit the human leukocyte common antigen-related (LAR) subfamily of protein tyrosine phosphatases (PTPs). Evidence supporting a postulated covalent ligation mechanism is provided herein.

Structure-activity relationship study of non-steroidal NPC1L1 ligands identified through cell-based assay using pharmacological chaperone effect as a readout

Niemann-Pick type C1-like 1 (NPC1L1) is an intestinal cholesterol transporter that is known to be the target of the cholesterol absorption inhibitor ezetimibe. We previously discovered steroidal NPC1L1 ligands by using a novel cell-based assay that employs pharmacological chaperone effect as a readout. Those steroid derivatives bound to a site different from both the sterol-binding domain and the ezetimibe-binding site, implying that they may be a novel class of NPC1L1 inhibitors with a distinct mode of action. As an extension of that work, we aimed here to find non-steroidal NPC1L1 ligands, which may be better candidates for clinical application than steroidal ligands, by using the same assay to screen our focused library of ligands for liver X receptor (LXR), a nuclear receptor that recognizes oxysterols as endogenous ligands. Here we describe identification of a novel class of NPC1L1 ligands with a ring-fused quinolinone scaffold, and an analysis of the structure-activity relationships of their derivatives as NPC1L1 ligands.

CuI/amino acid-catalyzed coupling and cyclization of β-bromo-α, β-unsaturated amides with terminal alkynes leading to (3Z)-3- alkylidenepyrrol-1-ones

β-Bromo-α,β-unsaturated amides are coupled and cyclized with terminal alkynes in DMF at 110 °C in the presence of a catalytic amount of CuI and amino acid along with a base to give the corresponding (3Z)-3-alkylidenepyrrol-1-ones in moderate to good yield

Palladium-catalyzed carbonylative cyclization of β-Bromo-α, β-unsaturated carboxylic acids leading to maleic anhydrides

β-Bromo-α,β-unsaturated carboxylic acids are carbonylatively cyclized under carbon monoxide pressure in acetic acid in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding maleic anhydrides in high yields. Georg Thieme Verlag Stuttgart · New York.

Pd/C-Catalyzed coupling and cyclization of β-bromo-α,β- unsaturated carboxylic acids with terminal alkynes leading to alkylidenefuranones

Palladium-catalyzed coupling of β-bromo-α,β-unsaturated carboxylic acids with terminal alkynes and subsequent regioselective 5-exo-dig cyclization produces (Z)-alkylidenefuranones in good yields.

Easy and efficient copper-catalyzed synthesis of bicyclic pyrimidinones under mild conditions

A simple and efficient copper-catalyzed method has been developed for synthesis of bicyclic pyrimidinones containing six-, seven-, eight-membered rings under mild conditions. The protocol uses readily available 2-bromocycloalk-1-enecarboxylic acids, amidines, and guanidines as the starting materials, copper-catalyzed cascade couplings provide the corresponding bicyclic pyrimidinones without addition of any ligand or additive, and the method is of economical and practical advantages. Georg Thieme Verlag Stuttgart New York.

Chemoselective benzylic C-H activations for the preparation of condensed N-heterocycles

Buttoning up: A chemoselective domino reaction including one or two successive C-H activations serves to convert a range of readily available N-arylpyrroles into complex polycondensed N-heterocycles. The reaction is catalyzed by Pd(OAc)2 (5 mol%), and p-Tol3P (10 mol%) is added as the ligand (see scheme; Tol = tolyl).

Concise synthesis of tetrahydrophenanthridone by palladium reagent

Heck reaction of N-(2-halophenyl)-N-methyl-1-cyclohexene-1carboxamide (1) and 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide (4) using a palladium reagent under several reaction conditions was examined. Reaction of 4 using Pd(OAc)2, DPPP, and Bu3P afforded tetrahydrophenanthridone (5) in excellent yield.

The Reactivity of 2-Substituted Cyclohex-1-enecarboxylic Acid With Diazodiphenylmethane in Various Alcohols

The reactivities of 2-substituted cyclohex-1-enecarboxylic acids with diazodiphenylmethane in several alcohols were investigated.The rate data for these acids were correlated with a simple Hammett equation by means of the ?p constants.The transmission of polar effects through the double bond, in terms of polar susceptibility constant ρ, has been discussed.For the reactions of a given acid in the various alcohols, the log k and ρ values were correlated through multiple regression on appropriate solvent parameters.The results obtained for 2-substituted cyclohex-1-enecarboxylic acids were compared with the results for ortho-substituted benzoic acids under the same experimental conditions.