2,5-二溴-3-噻吩羧酸乙酯 | 289470-44-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2,5-二溴-3-噻吩羧酸乙酯
• 中文别名: 2,5-二溴-3-噻吩甲酸乙酯；2,5-二溴噻吩-3-羧酸乙酯；2,5-二溴噻吩-3-甲酸乙酯
• 英文名称: ethyl 2,5-dibromothiophene-3-carboxylate
• CAS: 289470-44-6
• 化学式: C₇H₆Br₂O₂S
• 分子量: 313.997
• InChiKey: JJXKSBHSHSKQEX-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±35.0 °C(Predicted)
• 密度：
  1.895±0.06 g/cm3(Predicted)
• 熔点：
  35-37 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

概述

2,5-二溴-3-噻吩甲酸乙酯是一种多功能中间体，其中β-噻吩衍生物广泛应用于农药合成。

用途

2,5-二溴-3-噻吩甲酸乙酯作为一种酯类有机物，可用于钌催化的多羰基官能化酮的高选择性不对称氢化反应研究。

反应信息

• 作为反应物：
  描述：

  2,5-二溴-3-噻吩羧酸乙酯 在 四(三苯基膦)钯 、 正丁基锂 、 草酰氯 、 水 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-cyano-N-cyclopropyl-5-[1-[1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrrol-2-yl]pyrazol-4-yl]thiophene-3-carboxamide
  参考文献：
  名称：

  [EN] PESTICIDALLY ACTIVE PYRROLE DERIVATIVES
  [FR] DÉRIVÉS DE PYRROLE ACTIFS SUR LE PLAN PESTICIDE

  摘要：

  本发明涉及化合物(I)的配方，以及制备它们的方法，用于制备杀虫、杀螨、杀软体动物和杀线虫等农药组合物，以及使用它们来对抗和控制害虫，如昆虫、螨虫、软体动物和线虫害虫的方法。

  公开号：

  WO2019068820A1
• 作为产物：
  描述：

  2,5-二溴-3-噻吩甲酸 、 乙醇 在 氯化亚砜 、 碳酸氢钠 作用下， 以92%的产率得到2,5-二溴-3-噻吩羧酸乙酯
  参考文献：
  名称：

  HETEROCYCLIC COMPOUND AS GLUCAGON ANTAGONIST

  摘要：

  公开号：

  EP2210876B1

文献信息

• [EN] SUBSTITUTED PIPERAZINES OF AZEPINES, OXAZEPINES, AND THIAZEPINES<br/>[FR] PIPERAZINES SUBSTITUTEES D'AZEPINES, D'OXAZEPINES, ET DE THIAZEPINES
  申请人：LILLY CO ELI

  公开号：WO2005026177A1

  公开（公告）日：2005-03-24

  Described herein are antipyschotic compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; R1 is hydrogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, -CN, imidazolidin-2-one, phenyl, or tetrazole wherein tetrazole is unsubstituted or substituted with (C1-4) alkyl; R2 is H, halogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, OR6, SR6, NO2, CN, COR6, C(O)OR6, C(OH)R6, CONR7R8, phenyl or (C1-6) alkyl, wherein the (C1-6) alkyl is unsubstituted or substituted with a hydroxy; R3 is hydrogen, (C 1-6)fluoroalkyl , (C3-6) cycloalkyl, (C 2-6) alkenyl, phenyl, monocyclic heteroaromatic, bicyclic heteroaromatic, or (C1-4)alkyl wherein (C1-4) alkyl is unsubstituted or substituted with a phenyl; R4 and R5 are independently selected from hydrogen, halogen, (C1-6) alkyl, (C1-6) fluoroalkyl, OR9, SR9, NO2, CN, or COR9; R6 is hydrogen, (C1-6) fluoroalkyl, or (C1-6) alkyl; R7 and R8 are independently hydrogen, or (C1-6) alkyl; R9 is hydrogen, (C1-6) fluoroalkyl, (C1-6) alkyl; Alk is (C1-4) alkylene unsubstituted or substituted with a hydroxy; Y is oxygen, sulfur, SO2, or a bond; X is CH2, C=O, S, O, or SO2; Z is hydrogen, halogen, (C1-6) alkyl, (C1-6)fluoroalkyl, -OH, (C1-6) alkoxy, (C1-6) fluoroalkoxy, (C1-6) alkylthio, (C1-6) acyl, (C1-4)alkylsulfonyl, -OCF3, -NO2, - CN, carboxamido which may be substituted on the nitrogen by one or two (C1-4) alkyl groups, and -NH2 in which one of the hydrogens may be replaced by a (C1-4) alkyl group and the other hydrogen may be replaced by either a (C1-4) alkyl group, a (C1-6) acyl group, or a (C1-4) alkylsulfonyl group; the phenyl of R1, R2 or R3 is independently unsubstituted or substituted with one to three substituents independently selected from Z; the monocyclic heteroaromatic of R3 is unsubstituted or substituted with one to three substituents independently selected from Z; the bicyclic heteroaromatic of R3 is unsubstituted or substituted with one to three substituents independently selected from Z; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).

  本文描述了式(I)的抗精神病化合物，其中：是一个可选的苯并五元或六元芳香环，其中含有零至三个异原子，独立选择自N、O和S；R1是氢，(C1-6)氟烷基，(C3-6)环烷基，或(C1-4)烷基，其中(C1-4)烷基未取代或取代为羟基、甲氧基、乙氧基、OCH2CH2OH、-CN、咪唑烷-2-酮、苯基或四氮唑，其中四氮唑未取代或取代为(C1-4)烷基；R2是H、卤素、(C1-6)氟烷基、(C3-6)环烷基、OR6、SR6、NO2、CN、COR6、C(O)OR6、C(OH)R6、CONR7R8、苯基或(C1-6)烷基，其中(C1-6)烷基未取代或取代为羟基；R3是氢，(C1-6)氟烷基，(C3-6)环烷基，(C2-6)烯基，苯基，单环杂芳基，双环杂芳基，或(C1-4)烷基，其中(C1-4)烷基未取代或取代为苯基；R4和R5独立选择自氢、卤素、(C1-6)烷基、(C1-6)氟烷基、OR9、SR9、NO2、CN或COR9；R6是氢、(C1-6)氟烷基或(C1-6)烷基；R7和R8独立选择自氢或(C1-6)烷基；R9是氢、(C1-6)氟烷基或(C1-6)烷基；Alk是未取代或取代为羟基的(C1-4)烷基；Y是氧、硫、SO2或键；X是CH2、C=O、S、O或SO2；Z是氢、卤素、(C1-6)烷基、(C1-6)氟烷基、-OH、(C1-6)烷氧基、(C1-6)氟烷氧基、(C1-6)烷硫基、(C1-6)酰基、(C1-4)烷基磺酰基、-OCF3、-NO2、-CN、羧酰胺基，该羧酰胺基可在氮上被一个或两个(C1-4)烷基取代，以及-NH2，其中一个氢原子可被(C1-4)烷基取代，另一个氢原子可被(C1-4)烷基、(C1-6)酰基或(C1-4)烷基磺酰基取代；R1、R2或R3的苯基独立地未取代或取代为从Z中独立选择的一个至三个取代基；R3的单环杂芳基未取代或取代为从Z中独立选择的一个至三个取代基；R3的双环杂芳基未取代或取代为从Z中独立选择的一个至三个取代基；以及其盐、溶剂化合物和晶型形式。还描述了将式(I)的化合物用作多巴胺D2受体拮抗剂和治疗精神病和双相情感障碍的药物，以及式(I)的药物配方。
• Preparation of New Polyfunctional Magnesiated Heterocycles Using a Chlorine−, Bromine−, or Iodine−Magnesium Exchange
  作者：Mohamed Abarbri、Jérôme Thibonnet、Laurent Bérillon、Florian Dehmel、Mario Rottländer、Paul Knochel

  DOI：10.1021/jo000235t

  日期：2000.7.1

  iodine-magnesium exchange. In many cases, the exchange can be extended to heteroaryl bromides, and a case of a chlorine-magnesium exchange is described with tetrachlorothiophene. This new preparation of functionalized heteroarylmagnesium compounds provides after reaction with various electrophiles a new entry to a broad range of polyfunctional pyridines, imidazoles, furanes, thiophenes, pyrroles, antipyrines

  杂芳基碘化物与i-PrMgBr（约1.0当量）在THF中的反应提供了相应的镁化杂环。如果可以在-20摄氏度以下进行交换，这些新的格氏试剂中可以容忍酯基，氰基或氯化物等官能团。对于所有带有吸电子基团或螯合官能团的杂环，这种情况都有利于碘镁交换。在许多情况下，交换可扩展至杂芳基溴，并且描述了用四氯噻吩进行氯镁交换的情况。在与各种亲电试剂反应后，这种新的官能化的杂芳基镁化合物的制备为广泛的多官能吡啶，咪唑，呋喃，噻吩，吡咯，安替比林和尿嘧啶衍生物提供了新的入口。
• [EN] PESTICIDALLY ACTIVE THIOPHENE DERIVATIVES<br/>[FR] DÉRIVÉS DE THIOPHÈNE ACTIFS SUR LE PLAN PESTICIDE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2019030357A1

  公开（公告）日：2019-02-14

  Compounds of formula (I), as defined herein, to processes for preparing them, to pesticidal, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests.

  本发明涉及公式（I）所定义的化合物，以及制备它们的方法，以及包含它们的杀虫剂、杀螨剂、杀软体动物剂和杀线虫剂等农药组合物，以及使用它们来对抗和控制昆虫、螨虫、软体动物和线虫等害虫的方法。
• Substituted piperazines of azepines, oxazepines and thiazepines
  申请人：He Xiaoqiang John

  公开号：US20060270656A1

  公开（公告）日：2006-11-30

  Described herein are antipyschotic compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; R 1 is hydrogen, (C 1-6 ) fluoroalkyl, (C 3-6 ) cycloalkyl, or (C 1-4 ) alkyl, wherein the (C 1-4 ) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH 2 CH 2 OH, —CN, imidazolidin-2-one, phenyl, or tetrazole wherein tetrazole is unsubstituted or substituted with (C 1-4 ) alkyl; R 2 is H, halogen, (C 1-6 ) fluoroalkyl, (C 3-6 ) cycloalkyl, OR 6 , SR 6 , NO 2 , CN, COR 6 , C(O)OR 6 , C(OH)R 6 , CONR 7 R 8 , phenyl or (C 1-6 ) alkyl, wherein the (C 1-6 ) alkyl is unsubstituted or substituted with a hydroxy; R 3 is hydrogen, (C 1-6 )fluoroalkyl , (C 3-6 ) cycloalkyl, (C 2-6 ) alkenyl, phenyl, monocyclic heteroaromatic, bicyclic heteroaromatic, or (C 1-4 )alkyl wherein (C 1-4 ) alkyl is unsubstituted or substituted with a phenyl; R 4 and R 5 are independently selected from hydrogen, halogen, (C 1-6 ) alkyl, (C 1-6 ) fluoroalkyl, OR 9 , SR 9 , NO 2 , CN, or COR 9 ; R 6 is hydrogen, (C 1-6 ) fluoroalkyl, or (C 1-6 ) alkyl; R 7 and R 8 are independently hydrogen, or (C 1-6 ) alkyl; R 9 is hydrogen, (C 1-6 ) fluoroalkyl, (C 1-6 ) alkyl; Alk is (C 1-4 ) alkylene unsubstituted or substituted with a hydroxy; Y is oxygen, sulfur, SO 2 , or a bond; X is CH 2 , C═O, S, O, or SO 2 ; Z is hydrogen, halogen, (C 1-6 ) alkyl, (C 1-6 )fluoroalkyl, —OH, (C 1-6 ) alkoxy, (C 1-6 ) fluoroalkoxy, (C 1-6 ) alkylthio, (C 1-6 ) acyl, (C 1-4 )alkylsulfonyl, —OCF 3 , —NO 2 , —CN, carboxamido which may be substituted on the nitrogen by one or two (C 1-4 ) alkyl groups, and —NH 2 in which one of the hydrogens may be replaced by a (C 1-4 ) alkyl group and the other hydrogen may be replaced by either a (C 1-4 ) alkyl group, a (C 1-6 ) acyl group, or a (C 1-4 ) alkylsulfonyl group; the phenyl of R 1 , R 2 or R 3 is independently unsubstituted or substituted with one to three substituents independently selected from Z; the monocyclic heteroaromatic of R 3 is unsubstituted or substituted with one to three substituents independently selected from Z; the bicyclic heteroaromatic of R 3 is unsubstituted or substituted with one to three substituents independently selected from Z; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (I) as antagonists of the dopamine D 2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).

  本文描述了式(I)的抗精神病化合物，其中： - 是一个可选的苯并五元或六元芳香环，其具有0-3个杂原子，独立地选自N，O和S； - R1是氢，(C1-6)氟烷基，(C3-6)环烷基或(C1-4)烷基，其中(C1-4)烷基未取代或取代了羟基，甲氧基，乙氧基，OCH2CH2OH，—CN，咪唑啉-2-酮，苯基或四唑，其中四唑未取代或取代了(C1-4)烷基； - R2是H，卤素，(C1-6)氟烷基，(C3-6)环烷基，OR6，SR6，NO2，CN，COR6，C(O)OR6，C(OH)R6，CONR7R8，苯基或(C1-6)烷基，其中(C1-6)烷基未取代或取代了羟基； - R3是氢，(C1-6)氟烷基，(C3-6)环烷基，(C2-6)烯基，苯基，单环杂芳基，双环杂芳基或(C1-4)烷基，其中(C1-4)烷基未取代或取代了苯基； - R4和R5独立地选自氢，卤素，(C1-6)烷基，(C1-6)氟烷基，OR9，SR9，NO2，CN或COR9； - R6是氢，(C1-6)氟烷基或(C1-6)烷基； - R7和R8独立地是氢或(C1-6)烷基； - R9是氢，(C1-6)氟烷基或(C1-6)烷基； - Alk是(C1-4)烷基，未取代或取代了羟基； - Y是氧，硫，SO2或键； - X是CH2，C═O，S，O或SO2； - Z是氢，卤素，(C1-6)烷基，(C1-6)氟烷基，—OH，(C1-6)烷氧基，(C1-6)氟烷氧基，(C1-6)烷硫基，(C1-6)酰基，(C1-4)烷基磺酰基，—OCF3，—NO2，—CN，羧酰胺，其氮上可能通过一个或两个(C1-4)烷基取代，以及—NH2，在其中一个氢可能被(C1-4)烷基取代，另一个氢可能被(C1-4)烷基，(C1-6)酰基或(C1-4)烷基磺酰基取代； - R1，R2或R3的苯基独立地未取代或取代了1-3个Z取代基； - R3的单环杂芳基未取代或取代了1-3个Z取代基； - R3的双环杂芳基未取代或取代了1-3个Z取代基； - 还描述了该化合物的盐，溶剂化合物和晶体形式。 还描述了将式(I)化合物用作多巴胺D2受体拮抗剂和治疗精神病和双相障碍的药物，以及式(I)化合物的制剂。
• Heterocyclic compound
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US08309580B2

  公开（公告）日：2012-11-13

  The present invention provides a heterocyclic compound represented by the following formula (I), which has a glucagon antagonistic action and is useful for the prophylaxis or treatment of diabetes and the like, a compound represented by wherein ring A is an optionally substituted benzene ring and the like; Y is a nitrogen atom and the like; X is —O— and the like; R4 is a hydrogen atom and the like; R5 and R6 are each independently a hydrogen atom and the like; R1 is an optionally substituted hydrocarbon group and the like; R2 is a hydrogen atom and the like; and R3 is —(CH2)3—COOH and the like, or a salt thereof.

  本发明提供了一种杂环化合物，其由以下式子（I）表示，具有葡萄糖升高素拮抗作用，用于预防或治疗糖尿病等疾病，其中化合物由以下表示： 其中环A是可选取代的苯环等；Y是氮原子等；X是—O—等；R4是氢原子等；R5和R6各自独立地是氢原子等；R1是可选取代的烃基等；R2是氢原子等；R3是—（CH2）3—COOH等，或其盐。