2-Chloro-4-isopropyl-thiazole-5-carboxylic acid | 1194374-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Chloro-4-isopropyl-thiazole-5-carboxylic acid
• 英文别名: 2-Chloro-4-(1-methylethyl)-1,3-thiazole-5-carboxylic acid；2-chloro-4-propan-2-yl-1,3-thiazole-5-carboxylic acid
• CAS: 1194374-34-9
• 化学式: C₇H₈ClNO₂S
• 分子量: 205.665
• InChiKey: IFHJWSZHSBSJCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基苯基苯甲酮 、 2-Chloro-4-isopropyl-thiazole-5-carboxylic acid 在 polymer-bound EDC 作用下， 生成 2-Chloro-4-isopropyl-thiazole-5-carboxylic acid (3-benzoyl-phenyl)-amide
  参考文献：
  名称：

  Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides

  摘要：

  The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.

  DOI：

  10.1021/jo970571i

文献信息

• 2-Chloro-4,5-disubstituted-thiazoles, process for their preparation, use as antidotes against damage caused by herbicides and mixtures containing them
  申请人：MONSANTO COMPANY

  公开号：EP0027019A1

  公开（公告）日：1981-04-15

  2-chloro-4,5-disubstituted-thiazoles have been found to be effective in reducing herbicidal injury to sorghum plants due to the application thereto of acetanilide and thiocarbamate herbicides. The compounds of the present invention have the formula where R is equal to halogen, hydroxy, mercapto, methylthio, lower alkyl carbonyloxy, lower alkoxy, lower alkoxy carbonyl, lower alkoxy carbonyl (lower) alkoxy, lower alkoxy thioxomethylthio, benzyloxy, -NR2R3, R is lower alkyl, halo (lower) alkyl, phenyl or phenyl substituted by one to three groups, which may be the same or different, selected from the group consisting of halogen, lower alkyl, trifluoromethyl and cyano; R2 and R3 independently equal hydrogen, lower alkyl or lower alkenyl.

  研究发现，2-氯-4,5-二取代噻唑类化合物可有效减少乙酰苯胺类和硫代氨基甲酸酯类除草剂对高粱植物造成的除草伤害。 本发明的化合物具有如下式子 其中 R 等于卤素、羟基、巯基、甲硫基、低级烷基羰氧基、低级烷氧基、低级烷氧基羰基、低级烷氧基羰基（低级）烷氧基、低级烷氧基硫代甲硫基、苄氧基、-NR2R3、 R 是低级烷基、卤代（低级）烷基、苯基或被一至三个基团取代的苯基，这些基团可以相同或不同，选自卤素、低级烷基、三氟甲基和氰基组成的组；R2 和 R3 独立地等于氢、低级烷基或低级烯基。
• PROCESS FOR PREPARING THIAZOLECARBOXYLIC ACID CHLORIDES
  申请人：Mitsui Chemicals, Inc.

  公开号：EP0377750A1

  公开（公告）日：1990-07-18

  The invention provides a process for preparing thiazolecarboxylic acid chlorides represented by general formula (II) (wherein R1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a lower alkyl group substituted by a halogen atom or a lower alkoxy group, and R2 represents a hydrogen atom, a lower alkyl group optionally substituted by a halogen atom or a lower alkoxy group), which comprises reacting a thiazolecarboxylic acid represented by general formula (I) (wherein R1 and R2 are as defined above with respect to general formula (II) with phosgene or trichloromethyl chloroformate in the presence or absence of a catalyst.

  本发明提供了一种制备通式(II)代表的噻唑羧酸氯化物的工艺（其中R1代表氢原子、卤素原子、低级烷基、低级烷氧基或被卤素原子或低级烷氧基取代的低级烷基，R2代表氢原子、R1代表氢原子、低级烷基、低级烷氧基或被卤素原子或低级烷氧基取代的低级烷基，R2代表氢原子、低级烷基、低级烷氧基或被卤素原子或低级烷氧基取代的低级烷基），该反应包括在催化剂存在或不存在的情况下，将通式（I）代表的噻唑羧酸（其中 R1 和 R2 如上文通式（II）所定义）与光气或氯甲酸三氯甲酯反应。
• SYNTHESIS PROCESS OF DASATINIB AND INTERMEDIATE THEREOF
  申请人：Nanjing Cavendish Bio-Engineering Technology Co., Ltd.

  公开号：EP2532662B1

  公开（公告）日：2016-01-27
• US4199506A
  申请人：——

  公开号：US4199506A

  公开（公告）日：1980-04-22
• US4284426A
  申请人：——

  公开号：US4284426A

  公开（公告）日：1981-08-18