(E)-1-[2-bromovinyl]-2-trifluoromethylbenzene | 262268-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-[2-bromovinyl]-2-trifluoromethylbenzene
• 英文别名: 1-(2-bromovinyl)-2-(trifluoromethyl)benzene；1-(2-bromoethenyl)-2-(trifluoromethyl)benzene；(e)-1-(2-Bromovinyl)-2-(trifluoromethyl)benzene；1-[(E)-2-bromoethenyl]-2-(trifluoromethyl)benzene
• CAS: 262268-63-3
• 化学式: C₉H₆BrF₃
• 分子量: 251.046
• InChiKey: IHAVDPGJEMQOLT-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-[2-bromovinyl]-2-trifluoromethylbenzene 、 methyl (Z)-methoxyimino-[2-(2-tributylstannanylvinyl)phenyl]acetate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以21%的产率得到methyl (Z)-methoxyimino-{2-[(E,E)-4-(2-trifluoromethylphenyl)buta-1,3-dienyl]phenyl}acetate
  参考文献：
  名称：

  Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore

  摘要：

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.

  DOI：

  10.1021/jm990002y
• 作为产物：
  描述：

  邻三氟甲基苯甲醛 在 二乙基亚磷酸氢酯 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.75h， 生成 (E)-1-[2-bromovinyl]-2-trifluoromethylbenzene
  参考文献：
  名称：

  Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore

  摘要：

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.

  DOI：

  10.1021/jm990002y

文献信息

• Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
  作者：Wataru Kumaki、Hidenori Kinoshita、Katsukiyo Miura

  DOI：10.1016/j.tet.2022.132687

  日期：2022.3

  hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal

  已经研究了用市售的溴化氢在乙酸中的溶液对末端和内部炔烃进行均裂氢溴化反应，以用于溴代烯烃的区域选择性和立体选择性合成。在室温下的有氧气氛下，乙炔基芳烃与少量过量的 HBr 反应有效地产生了具有良好至高E选择性的 (2-溴乙烯基) 芳烃。(Alk-1-ynyl) 芳烃或在 sp-碳上同时带有苯基和烷基的内部炔烃也经历了空气引发的溴化氢反应，在使用半当量 HBr 的动力学条件下表现出高Z选择性。
• .beta.-Alkoxyacrylates against malaria
  申请人：Hoffmann-La Roche Inc.

  公开号：US06084120A1

  公开（公告）日：2000-07-04

  The present invention relates to compounds having the formulae ##STR1## wherein R, R.sup.1, R.sup.6, R.sup.7, Rn.sup.8, X, and Z are defined herein, which are useful in the treatment or prophylaxis of malaria. The compounds of the present invention are especially useful in the treatment or prophylaxis of chloroquine-sensitive and chloroquine-resistant malaria.

  本发明涉及具有以下结构的化合物 ##STR1## 其中R、R.sup.1、R.sup.6、R.sup.7、Rn.sup.8、X和Z在此定义，这些化合物在治疗或预防疟疾方面具有用途。本发明的化合物在治疗或预防对氯喹敏感和氯喹耐药性疟疾方面特别有用。
• [EN] beta -ALKOXYACRYLATES AGAINST MALARIA<br/>[FR] BETA-ALCOXYACRYLATES CONTRE LA MALARIA
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：WO1999002150A1

  公开（公告）日：1999-01-21

  (EN) The invention relates to the use of $g(b)-alkoxyacrylates of formulae (IA) or (IB) wherein R, R1, R6, R7, R8, X and Z are as defined herein, as therapeutically active substances, especially in the treatment or prophylaxis of malaria and to medicaments containing these substances.(FR) L'invention concerne l'utilisation de $g(b)-alcoxyacrylates de formule (IA) ou (IB), dans lesquelles R, R1, R6, R7, R8, X et Z sont conformes au descriptif, en tant que composants thérapeutiques actifs dans le traitement ou la prophylaxie de la malaria, ainsi que des médicaments contenant ces composants.

  本发明涉及使用公式（IA）或（IB）中R，R1，R6，R7，R8，X和Z如本文所定义的$g(b)-烷氧基丙烯酸酯作为治疗活性物质，特别是在治疗或预防疟疾方面的应用，以及包含这些物质的药物。
• ——
  作者：A. V. Shastin、V. G. V. G.、V. N. Korotchenko、E. S. Balenkova

  DOI：10.1023/a:1012780906226

  日期：——

  A new stereoselective method was developed for the synthesis of beta-bromostyrenes (E/Z > 5/1) starting from hydrazones of aromatic aldehydes and bromoform in the presence of CuCl.
• $g(b)-ALKOXYACRYLATES AGAINST MALARIA
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0996439A1

  公开（公告）日：2000-05-03