2-(1-(thiophen-2-yl)-3-oxo-3-phenylpropyl)malononitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-(thiophen-2-yl)-3-oxo-3-phenylpropyl)malononitrile
• 英文别名: (-)-2-(1-(2-thienyl)-3-oxo-3-phenylpropyl)malononitrile；2-[(1R)-3-oxo-3-phenyl-1-thiophen-2-ylpropyl]propanedinitrile
• 化学式: C₁₆H₁₂N₂OS
• 分子量: 280.35
• InChiKey: AODUFQZOKUAUPI-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(2'-thienyl)acrylophenone 、 丙二腈 在 aluminum isopropoxide 、 奎宁 作用下， 以 甲苯 为溶剂， 反应 81.0h， 生成 2-(1-(thiophen-2-yl)-3-oxo-3-phenylpropyl)malononitrile 、 2-(1-(thiophen-2-yl)-3-oxo-3-phenylpropyl)malononitrile
  参考文献：
  名称：

  通过简单的奎宁-Al（O（i）Pr）（3）配合物催化丙二醛向查尔酮的对映选择性迈克尔加成反应：一种合成手性4H-吡喃衍生物的简单方法。

  摘要：

  通过简单的奎宁和Al（O（i）Pr）（3）配合物催化丙二醛向对苯二酚的对映选择性迈克尔加成反应，并获得了良好的ee和高收率的产物，这促进了具有生物活性的4H-的不对称合成吡喃化合物。

  DOI：

  10.1039/b908632c

文献信息

• Chloramphenicol base chemistry. Part 11: 1 chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α , β -unsaturated ketones
  作者：Linjie Yan、Haifeng Wang、Fangjun Xiong、Yuan Tao、Yan Wu、Fener Chen

  DOI：10.1016/j.tetasy.2017.05.015

  日期：2017.7

  The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to alpha,beta-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various alpha,beta-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X(7) receptor antagonists. (C) 2017 Published by Elsevier Ltd.
• The asymmetric addition of malononitrile to α,β-unsaturated ketones catalyzed by RuCl2[(R,R)-DPEN](PPh3)2 as the precatalyst
  作者：Xuefeng Li、Yaping Ma、Zhikui Xing、Ning Tang、Jin Zhu、Jingen Deng

  DOI：10.1016/j.tetlet.2014.04.045

  日期：2014.7

  Non-borohydride ruthenium complex, RuCl2[(R,R)-DPEN](PPh3)(2) (1f), was demonstrated to catalyze asymmetric Michael addition of malononitrile to acyclic enones with weak bases. Michael addition of malononitrile to chalcone and analogues was promoted by combining CsOAc with CsOH in the presence of 1f and gave good yields and up to 82% ee. (C) 2014 Elsevier Ltd. All rights reserved.
• Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine–Al(OiPr)3 complex: a simple method for the synthesis of a chiral 4H-pyran derivative
  作者：Jian Shi、Min Wang、Ling He、Ke Zheng、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1039/b908632c

  日期：——

  Enantioselective Michael addition of malononitrile to chalcones was catalyzed by a simple quinine and Al(O(i)Pr)(3) complex and products were obtained in good ee as well as high yields, which facilitated the asymmetric synthesis of a biologically active 4H-pyran compound.

  通过简单的奎宁和Al（O（i）Pr）（3）配合物催化丙二醛向对苯二酚的对映选择性迈克尔加成反应，并获得了良好的ee和高收率的产物，这促进了具有生物活性的4H-的不对称合成吡喃化合物。