methyl (E)-3-(4-chloro-2-fluorophenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-(4-chloro-2-fluorophenyl)acrylate
• 英文别名: methyl(2E)-3-(4-chloro-2-fluorophenyl)prop-2-enoate；methyl (E)-3-(4-chloro-2-fluorophenyl)prop-2-enoate
• 化学式: C₁₀H₈ClFO₂
• 分子量: 214.624
• InChiKey: OCGRVPULGVALNH-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(4-chloro-2-fluorophenyl)acrylate 在 potassium cyanide 、 羟胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以15%的产率得到(2E)-3-(4-chloro-2-fluorophenyl)-N-hydroxyprop-2-enamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors

  摘要：

  Botulinum neurotoxins are the most toxic proteins currently known. Based on a recently identified potent lead structure, 2,4-dichlorocinnamic acid hydroxamate, herein we report on the structure- activity relationship of a series of hydroxamate BoNT/A inhibitors. Among them, 2-bromo-4-chlorocinnamic acid hydroxamate, 2-methyl-4-chlorocinnamic acid hydroxamate, and 2-trifluoromethyl-4-chlorocinnamic acid hydroxamate displayed comparable inhibitory activity to that of the lead structure. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.103
• 作为产物：
  描述：

  膦酰基乙酸甲酯二乙酯 、 4-氯-2-氟苯甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以78%的产率得到methyl (E)-3-(4-chloro-2-fluorophenyl)acrylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors

  摘要：

  Botulinum neurotoxins are the most toxic proteins currently known. Based on a recently identified potent lead structure, 2,4-dichlorocinnamic acid hydroxamate, herein we report on the structure- activity relationship of a series of hydroxamate BoNT/A inhibitors. Among them, 2-bromo-4-chlorocinnamic acid hydroxamate, 2-methyl-4-chlorocinnamic acid hydroxamate, and 2-trifluoromethyl-4-chlorocinnamic acid hydroxamate displayed comparable inhibitory activity to that of the lead structure. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.103

文献信息

• Iron-Catalyzed Carboamination of Olefins: Synthesis of Amines and Disubstituted β-Amino Acids
  作者：Bo Qian、Shaowei Chen、Ting Wang、Xinhao Zhang、Hongli Bao

  DOI：10.1021/jacs.7b06590

  日期：2017.9.20

  Intermolecular carboamination of olefins with general alkyl groups is an unsolved problem. Diastereoselective carboamination of acyclic olefins represents an additional challenge in intermolecular carboaminations. We have developed a general alkylamination of vinylarenes and the unprecedented diastereoselective anti-carboamination of unsaturated esters, generating amines and unnatural β-amino acids

  具有一般烷基的烯烃的分子间碳氨基化是一个未解决的问题。无环烯烃的非对映选择性碳胺化代表了分子间碳胺化的额外挑战。我们开发了乙烯基芳烃的一般烷基胺化和前所未有的不饱和酯的非对映选择性抗碳胺化，生成胺和非天然 β-氨基酸。这种烷基胺化是通过双官能烷基化试剂和铁催化剂实现的。很容易从脂肪酸合成的烷基二酰基过氧化物既可用作烷基化试剂，也可用作内部氧化剂。一项计算研究表明，将腈添加到碳正离子中是决定非对映选择性的步骤，并且提出了超共轭来解释高度非对映选择性的抗碳化。
• Synthesis and SAR of potent and orally bioavailable tert-butylpyrrolidine archetype derived melanocortin subtype-4 receptor modulators
  作者：Liangqin Guo、Zhixiong Ye、Feroze Ujjainwalla、Heather L. Sings、Iyassu K. Sebhat、John Huber、David H. Weinberg、Rui Tang、Tanya MacNeil、Constantin Tamvakopoulos、Qianping Peng、Euan MacIntyre、Lex H.T. van der Ploeg、Mark T. Goulet、Matthew J. Wyvratt、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2008.04.049

  日期：2008.6

  Discovery of a series of tert-butyl pyrrolidine derived, potent and orally bioavailable melanocortin receptor subtype-4 (MC4R) selective modulators is disclosed. (C) 2008 Elsevier Ltd. All rights reserved.
• CN115477606
  申请人：——

  公开号：——

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