2-(1-(2-methoxyphenyl)-3-oxo-3-phenylpropyl)malononitrile | 1352995-83-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-(1-(2-methoxyphenyl)-3-oxo-3-phenylpropyl)malononitrile
• 英文别名: (S)-2-[1-(2-methoxyphenyl)-3-oxo-3-phenylpropyl]malononitrile
• CAS: 1352995-83-5
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: SXKJEKWNGIPLEF-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.88
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-methoxychalcone 、 丙二腈 在 萘酚 、 奎宁 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以82%的产率得到
  参考文献：
  名称：

  Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect

  摘要：

  2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with alpha-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when a-naphthol was employed as additive. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.08.013

文献信息

• Squaramide-catalyzed enantioselective Michael addition of malononitrile to chalcones
  作者：Wen Yang、Yang Jia、Da-Ming Du

  DOI：10.1039/c1ob06302b

  日期：——

  A highly enantioselective Michael addition of malononitrile to chalcones catalyzed by a chiral quinine-derived squaramide catalyst has been developed. This organocatalytic reaction at a very low catalyst loading (0.5 mol%) led to chiral γ-cyano carbonyl compounds in good yields with high enantioselectivities (up to 96% ee) under mild reaction conditions.

  对映体的高对映选择性迈克尔加成 丙二腈已经开发了由手性奎宁衍生的方酰胺催化剂催化的查耳酮。在非常低的催化剂负载量（0.5摩尔％）下，这种有机催化反应在温和的反应条件下以高收率和高对映选择性（最高96％ee）产生了手性的γ-氰基羰基化合物。