5-溴噻吩-2-甲酸丙-2-酯 | 1174013-07-0

• 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: 5-溴噻吩-2-甲酸丙-2-酯
• 英文名称: isopropyl 5-bromo-2-thiophenecarboxylate
• 英文别名: Propan-2-yl 5-bromothiophene-2-carboxylate
• CAS: 1174013-07-0
• 化学式: C₈H₉BrO₂S
• mdl: MFCD21101334
• 分子量: 249.128
• InChiKey: LVELELOTXWYCDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-溴噻吩-2-甲酸丙-2-酯 、 2-丙炔-1-醇 在 copper(l) iodide 、 四(三苯基膦)钯 、 二乙胺 作用下， 生成 isopropyl 5-(3-hydroxyprop-1-yn-1-yl)thiophene-2-carboxylate
  参考文献：
  名称：

  Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

  摘要：

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.092
• 作为产物：
  描述：

  5-溴-2-羧基噻吩 、 异丙醇 在 盐酸 作用下， 生成 5-溴噻吩-2-甲酸丙-2-酯
  参考文献：
  名称：

  Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

  摘要：

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.092

文献信息

• Successive Pd‐Catalyzed Decarboxylative Cross‐Couplings for the Modular Synthesis of Non‐Symmetric Di‐Aryl‐Substituted Thiophenes
  作者：Cynthia Messina、Liam Z. Douglas、Jiang Tian Liu、Pat Forgione

  DOI：10.1002/ejoc.202000780

  日期：2020.8.31

  ester‐protected acid moieties, is utilized as a starting material for the efficient synthesis of an array of non‐symmetric, di‐aryl‐substituted thiophene through successive decarboxylative palladium‐catalyzed couplings, with an intermediate saponification step.

  通过连续的脱羧钯催化偶合反应，将具有相对的溴化物和酯保护的酸部分的噻吩结构单元用作有效合成一系列非对称，二芳基取代的噻吩的原料。皂化步骤。
• Synthesis of 2-thiophenecarboxylic and 2,5-thiophenedicarboxylic acid esters via the reaction of thiophenes with the CCl4-ROH reagent in the presence of vanadium, iron, and molybdenum catalysts
  作者：R. I. Khusnutdinov、N. A. Shchadneva、A. R. Baiguzina、R. R. Mukminov、Yu. Yu. Mayakova、A. A. Smirnov、U. M. Dzhemilev

  DOI：10.1134/s0965544108060121

  日期：2008.11

  2-Thiophenecarboxylic and 2,5-thiohenedicarboxylic acid esters were synthesized via the reaction of thiophene with the CCl(4)-ROH-catalyst system, with a total yield of 44-85%. A possible reaction scheme includes the successive steps of alkylation of thiophene with carbon tetrachloride, leading to 2-trichloromethylthiophene, and alcoholysis of the product giving the corresponding 2-thiophenecarboxylate. The best catalysts for this reaction are VO(acac)(2), Fe(acac)(3), and Mo(CO)(6).
• Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation
  作者：Sajiv K. Nair、Jean J. Matthews、Stephan J. Cripps、Chunrong Ma、Elena Z. Dovalsantos、Alan W. Grubbs、Neal W. Sach、Wolter ten Hoeve、Han Koster、Erik J. Flahive、Steven P. Tanis、Matt Renner、Jim van Wiltenburg

  DOI：10.1016/j.tetlet.2009.12.092

  日期：2010.3

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.