tert-butyl (E)-(4-dimethylaminobenzylidene)cyanoacetate

• 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: tert-butyl (E)-(4-dimethylaminobenzylidene)cyanoacetate
• 英文别名: 2-Propenoic acid, 2-cyano-3-[4-(dimethylamino)phenyl]-, 1,1-dimethylethyl ester；tert-butyl (E)-2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enoate
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: ATYKGOWJOOUMDX-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-(4-dimethylaminobenzylidene)cyanoacetate 在 三氟乙酸 作用下， 生成 (E)-2-cyano-3-(4-(dimethylamino)phenyl)acrylic acid
  参考文献：
  名称：

  Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

  摘要：

  A novel class of low molecular weight protein tyrosine kinase inhibitors is described. These compounds constitute a systematic series of molecules with a progressive increase in affinity toward the substrate site of the EGF receptor kinase domain. These competitive inhibitors also effectively block the EGF-dependent autophosphorylation of the receptor. The potent EGF receptor kinase blockers examined were found to competitively inhibit the homologous insulin receptor kinase at 10(2)-10(3) higher inhibitor concentrations in spite of the significant homology between these protein tyrosine kinases. These results demonstrate the ability to synthesize selective tyrosine kinase inhibitors. The most potent EGF receptor kinase inhibitors also inhibit the EGF-dependent proliferation of A431/clone 15 cells with little or no effect on EGF independent cell growth. These results demonstrate the potential use of protein tyrosine kinase inhibitors as selective antiproliferative agents for proliferative diseases caused by the hyperactivity of protein tyrosine kinases. We have suggested the name "tyrphostins" for this class of antiproliferative compounds which act as protein tyrosine kinase blockers.

  DOI：

  10.1021/jm00130a020
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 氰乙酸叔丁酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以90%的产率得到tert-butyl (E)-(4-dimethylaminobenzylidene)cyanoacetate
  参考文献：
  名称：

  由醇盐-氢硅烷系统实现的全氟芳烃与 α,β-不饱和羰基的共轭加成：自由基途径的意义

  摘要：

  有机金属试剂与α,β-不饱和羰基化合物的共轭加成是有机合成中碳-碳键构建的关键策略。尽管近年来探索了通过过渡金属催化将 CH 直接加成到不饱和键，但不带有导向基团的缺电子芳烃仍然具有挑战性。在本文中，我们公开了由醇盐-氢硅烷系统实现的全氟芳烃与 α,β-不饱和羰基的共轭加成的第一个例子。该反应可方便地在室温下在广泛的底物和反应物上进行，以提供高产率到极好的合成多功能产品。结合计算研究的机械实验表明，在这种转变中最有可能是一个激进的途径。

  DOI：

  10.1021/jacs.8b05744

文献信息

• GAZIT, AVIV;YAISH, PNINA;GILON, CHAIM;LEVITZKI, ALEXANDER, J. MED. CHEM., 32,(1989) N0, C. 2344-2352
  作者：GAZIT, AVIV、YAISH, PNINA、GILON, CHAIM、LEVITZKI, ALEXANDER

  DOI：——

  日期：——
• Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors
  作者：Aviv Gazit、Pnina Yaish、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm00130a020

  日期：1989.10

  A novel class of low molecular weight protein tyrosine kinase inhibitors is described. These compounds constitute a systematic series of molecules with a progressive increase in affinity toward the substrate site of the EGF receptor kinase domain. These competitive inhibitors also effectively block the EGF-dependent autophosphorylation of the receptor. The potent EGF receptor kinase blockers examined were found to competitively inhibit the homologous insulin receptor kinase at 10(2)-10(3) higher inhibitor concentrations in spite of the significant homology between these protein tyrosine kinases. These results demonstrate the ability to synthesize selective tyrosine kinase inhibitors. The most potent EGF receptor kinase inhibitors also inhibit the EGF-dependent proliferation of A431/clone 15 cells with little or no effect on EGF independent cell growth. These results demonstrate the potential use of protein tyrosine kinase inhibitors as selective antiproliferative agents for proliferative diseases caused by the hyperactivity of protein tyrosine kinases. We have suggested the name "tyrphostins" for this class of antiproliferative compounds which act as protein tyrosine kinase blockers.
• Conjugate Addition of Perfluoroarenes to α,β-Unsaturated Carbonyls Enabled by an Alkoxide-Hydrosilane System: Implication of a Radical Pathway
  作者：Weilong Xie、Sung-Woo Park、Hoimin Jung、Dongwook Kim、Mu-Hyun Baik、Sukbok Chang

  DOI：10.1021/jacs.8b05744

  日期：2018.8.1

  reagents to α,β-unsaturated carbonyls is a key strategy for the construction of carbon-carbon bond in organic synthesis. Although direct C-H addition to unsaturated bonds via transition metal catalysis is explored in recent years, electron-deficient arenes that do not bear directing groups continue to be challenging. Herein we disclose the first example of a conjugate addition of perfluoroarenes to α,β-unsaturated

  有机金属试剂与α,β-不饱和羰基化合物的共轭加成是有机合成中碳-碳键构建的关键策略。尽管近年来探索了通过过渡金属催化将 CH 直接加成到不饱和键，但不带有导向基团的缺电子芳烃仍然具有挑战性。在本文中，我们公开了由醇盐-氢硅烷系统实现的全氟芳烃与 α,β-不饱和羰基的共轭加成的第一个例子。该反应可方便地在室温下在广泛的底物和反应物上进行，以提供高产率到极好的合成多功能产品。结合计算研究的机械实验表明，在这种转变中最有可能是一个激进的途径。