2,3-dibromo-4'-chlorocinnamic acid ethyl ester | 35282-97-4

• 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: 2,3-dibromo-4'-chlorocinnamic acid ethyl ester
• 英文别名: 2-(4-Chlorphenyl)-1,2-dibrompropionsaeureethylester；Ethyl 2,3-dibromo-3-(4-chlorophenyl)propanoate
• CAS: 35282-97-4
• 化学式: C₁₁H₁₁Br₂ClO₂
• 分子量: 370.468
• InChiKey: AWXVWHGHUTUGAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dibromo-4'-chlorocinnamic acid ethyl ester 在 potassium tert-butylate 作用下， 生成 (4-氯苯基)-丙酸乙酯
  参考文献：
  名称：

  Transmission of substituent effects through extended systems—III. p-Substituted ethyl trans cinnamates and phenylpropiolates

  摘要：

  DOI：

  10.1016/0584-8539(82)80085-8
• 作为产物：
  描述：

  ethyl-p-chlorocinnamate 在 溴 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2,3-dibromo-4'-chlorocinnamic acid ethyl ester
  参考文献：
  名称：

  14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

  摘要：

  14 beta-4'-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity, which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a's codeinone equivalent 3a, which had potent antinociceptive activity.

  DOI：

  10.1021/jm901074a

文献信息

• New One-Step Synthesis of Functionalized 2-Imidazolines
  作者：Alain Marsura、Cuong Luu-Duc、Gisèle Gellon

  DOI：10.1055/s-1985-31267

  日期：——
• MARSURA, A.;DUC, GUONG, LUU, SYNTHESIS, BRD, 1982, N 7, 545
  作者：MARSURA, A.、DUC, GUONG, LUU

  DOI：——

  日期：——
• MARSURA, A.;LUU-DUC, CUONG;GELLON, G., SYNTHESIS, BRD, 1985, N 5, 537-541
  作者：MARSURA, A.、LUU-DUC, CUONG、GELLON, G.

  DOI：——

  日期：——
• 14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists
  作者：Nick P.R. Nieland、David Rennison、Jillian H. Broadbear、Lauren Purington、James H. Woods、John R. Traynor、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm901074a

  日期：2009.11.12

  14 beta-4'-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity, which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a's codeinone equivalent 3a, which had potent antinociceptive activity.
• Transmission of substituent effects through extended systems—III. p-Substituted ethyl trans cinnamates and phenylpropiolates
  作者：G. Butt、R.D. Topsom

  DOI：10.1016/0584-8539(82)80085-8

  日期：1982.1