2-acetyl-3-(3-chlorophenyl)-acrylic acid (2-cyanoethyl) ester | 314775-78-5

• 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: 2-acetyl-3-(3-chlorophenyl)-acrylic acid (2-cyanoethyl) ester
• 英文别名: 2-(3-chlorobenzylidene)acetoacetic acid 2-cyanoethyl ester；2-cyanoethyl 2-acetyl-3-(3-chlorophenyl)acrylate；2-cyanoethyl 2-[(3-chlorophenyl)methylidene]-3-oxobutanoate
• CAS: 314775-78-5
• 化学式: C₁₄H₁₂ClNO₃
• 分子量: 277.707
• InChiKey: LIXPJUPATXZKPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-(3-chlorophenyl)-acrylic acid (2-cyanoethyl) ester 在 ammonium acetate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 11.0h， 生成 (+)-4-(3-chlorophenyl)-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid cinnamyl ester 5-(2-cyanoethyl) ester
  参考文献：
  名称：

  Asymmetric synthesis and biological evaluations of (+)- and (−)-6-dimethoxymethyl-1,4-dihydropyridine-3-carboxylic acid derivatives blocking N-type calcium channels

  摘要：

  An efficient asymmetric synthesis of 1,4-dihydropyridine derivatives is described. The key step is the stereoselective Michael addition using t-butyl ester of L-valine as a chiral auxiliary to achieve good ee (>95% for all the tested experiments) and moderate yield. With this method, (+)-4-(3-chlorophenyl)-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid cinnamyl ester was obtained and was characterized as a promising N-type calcium channel blocker with improved selectivity over L-type compared to its (-)- and racemic isomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.007
• 作为产物：
  描述：

  3-氯苯乙烯 、 2-氰基乙酰乙酸乙酯 在 哌啶 、 溶剂黄146 作用下， 以 propanol, 2 为溶剂， 以100%的产率得到2-acetyl-3-(3-chlorophenyl)-acrylic acid (2-cyanoethyl) ester
  参考文献：
  名称：

  EP1191021

  摘要：

  公开号：

文献信息

• Pyrimidine derivatives and new pyridine derivatives
  申请人：AJINOMOTO CO., INC.

  公开号：US20040009991A1

  公开（公告）日：2004-01-15

  Achirai pyrimidine derivatives and pyridine derivatives of the following formulae or analogs thereof have selective N-type calcium channel antagonistic activity and showed analgesic action when they were taken orally. They are useful as therapeutic agents for pains and various diseases associated with the N-type calcium channels. 1

  Achirai嘧啶衍生物和以下结构式或其类似物的吡啶衍生物具有选择性N型钙通道拮抗活性，并在口服时显示镇痛作用。它们可用作与N型钙通道相关的疼痛和各种疾病的治疗药物。
• Dihydropyridine derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US07247645B2

  公开（公告）日：2007-07-24

  Compounds having a selective N-type calcium channel antagonistic activity are provided. Dihydropyridine derivatives represented by the following formula: analogs thereof and pharmaceutically acceptable salts thereof have an activity of selectively inhibiting the action of N-type calcium channel, and they are used as therapeutic agents for various diseases relating to N-type calcium channel.

  提供了具有选择性N型钙通道拮抗活性的化合物。以下式表示的二氢吡啶衍生物：其类似物和药学上可接受的盐具有选择性抑制N型钙通道作用的活性，并且它们被用作与N型钙通道相关的各种疾病的治疗剂。