trans-3-(4-bromothiophen-2-yl)-acryloyl chloride | 104082-32-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: trans-3-(4-bromothiophen-2-yl)-acryloyl chloride
• 英文别名: (E)-3-(4-bromo-2-thienyl)acrylic acid chloride；(E)-3-(4-bromothiophen-2-yl)prop-2-enoyl chloride
• CAS: 104082-32-8
• 化学式: C₇H₄BrClOS
• 分子量: 251.531
• InChiKey: DBLWHBKGSUYQEM-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-3-(4-bromothiophen-2-yl)-acryloyl chloride 在 palladium diacetate 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 [(1R,2R)-2-(4-bromothiophen-2-yl)cyclopropyl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone
  参考文献：
  名称：

  Vallaerda, Jerk; Appelberg, Ulf; Csoeregh, Ingeborg, Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 461 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-3-(4-溴-2-噻吩基)丙烯酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 trans-3-(4-bromothiophen-2-yl)-acryloyl chloride
  参考文献：
  名称：

  非硫醇法呢基转移酶抑制剂：芳基噻吩基丙烯酰氨基二苯甲酮对远芳基结合位点的利用

  摘要：

  我们最近描述了法呢基转移酶的两个新的芳基结合位点。结果证明，4- 和 5- 芳基取代的噻吩基丙烯酰基部分是我们基于二苯甲酮的 AAX（能够占据远芳基结合位点的肽模拟物）的合适替代品。

  DOI：

  10.1002/ardp.200400886

文献信息

• Thienopyridine and furopyridine kinase inhibitors
  申请人：Betschmann Patrick

  公开号：US20050043347A1

  公开（公告）日：2005-02-24

  Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有以下化学式的化合物对抑制蛋白酪氨酸激酶具有用处。本发明还公开了制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• MORPHINAN DERIVATIVE AND MEDICINAL USE
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0663401A1

  公开（公告）日：1995-07-19

  A morphinan derivative represented by formula (1) or a pharmacologically acceptable acid-addition salt thereof, and analgesic, diuretic, antitussive and brain cell protective agents each containing the derivative or the salt as the active ingredient. These compounds have potent analgesic, diuretic and antitussive effects as a highly selective κ-opioid agonist, and are useful as analgesic, diuretic and antitussive agents. In addition, they have a significant brain cell protective effect and are useful as a brain cell protective agent.

  由式（1）代表的吗啡南衍生物或其药理学上可接受的酸加成盐，以及含有该衍生物或盐作为活性成分的镇痛剂、利尿剂、镇咳剂和脑细胞保护剂。这些化合物作为一种高选择性κ-类阿片激动剂，具有强效的镇痛、利尿和镇咳作用，可用作镇痛、利尿和镇咳制剂。此外，它们还具有明显的脑细胞保护作用，可用作脑细胞保护剂。
• Thienopyridine urea inhibitors of KDR kinase
  作者：H. Robin Heyman、Robin R. Frey、Peter F. Bousquet、George A. Cunha、Maria D. Moskey、Asma A. Ahmed、Niru B. Soni、Patrick A. Marcotte、Lori J. Pease、Keith B. Glaser、Melinda Yates、Jennifer J. Bouska、Daniel H. Albert、Candace L. Black-Schaefer、Peter J. Dandliker、Kent D. Stewart、Paul Rafferty、Steven K. Davidsen、Michael R. Michaelides、Michael L. Curtin

  DOI：10.1016/j.bmcl.2006.12.015

  日期：2007.3

  A series of substituted thienopyridine ureas was prepared and evaluated for enzymatic and cellular inhibition of KDR kinase activity. Several of these analogs, such as 2, are potent inhibitors of KDR (<10 nM) in both enzymatic and cellular assays. Further characterization of inhibitor 2 indicated that this analog possessed excellent in vivo potency (ED50 2.1 mg/kg) as measured in an estradiol-induced mouse uterine edema model.
• Discovery of thienopyridines as Src-family selective Lck inhibitors
  作者：Lily Abbott、Patrick Betschmann、Andrew Burchat、David J. Calderwood、Heather Davis、Peter Hrnciar、Gavin C. Hirst、Biqin Li、Michael Morytko、Kelly Mullen、Bryant Yang

  DOI：10.1016/j.bmcl.2006.12.035

  日期：2007.3

  We describe the identification, SAR, and in vivo pharmacology of a new series of Src-family selective Lck inhibitors. These thienopyridines were designed based on a desire to access the unique residues in the extended hinge region of Lck. (c) 2006 Elsevier Ltd. All rights reserved.
• Improved Synthesis of 3-Substituted-4-amino-[3,2-<i>c</i>]-thienopyridines
  作者：Kenneth M. Engstrom、Amanda L. Baize、Thaddeus S. Franczyk、Jeffrey M. Kallemeyn、Mathew M. Mulhern、Robert C. Rickert、Seble Wagaw

  DOI：10.1021/jo9003772

  日期：2009.5.15

  Two syntheses of 3-substituted-4-amino-[3,2-c]thienopyridines have been developed to replace the standard literature route to these compounds, which uses unattractive conditions involving azide and high temperatures. The first synthesis utilizes a Friedel-Crafts reaction as its key ring-forming step, whereas the second route relies on an unprecedented intramolecular reductive cyclization between a nitroolefin and a nitrile as its key ring-forming step. The development and optimization of each 3-substituted-4amino-[3,2-c]thienopyridine synthesis is discussed and a comparison of the routes is presented.