2-(1-(4-cyanophenyl)-3-oxo-3-phenylpropyl)malononitrile | 1376529-17-7

• 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-(4-cyanophenyl)-3-oxo-3-phenylpropyl)malononitrile
• 英文别名: 2-[1-(4-Cyanophenyl)-3-oxo-3-phenylpropyl]propanedinitrile；2-[1-(4-cyanophenyl)-3-oxo-3-phenylpropyl]propanedinitrile
• CAS: 1376529-17-7
• 化学式: C₁₉H₁₃N₃O
• 分子量: 299.332
• InChiKey: OOCWKCPTKVCPOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  88.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-(4-cyanophenyl)-3-oxo-3-phenylpropyl)malononitrile 在 magnesium bis(monoperoxyphthalate)hexahydrate 、 lithium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  一锅奎宁催化的α-手性γ-酮酯的合成：富含对映体的顺式α，γ取代的γ-丁内酯

  摘要：

  通过结合奎宁催化的丙二醛向反式烯酮的迈克尔加成反应以及随后的单过氧邻苯二甲酸镁（MMPP）氧化反应，已经开发出了对映体选择性很强的重要组成部分，α-手性γ-酮酯。这些合成子被证明是有用的试剂，用于以良好的非对映选择性和高对映体控制容易地获得具有挑战性的顺式， α，γ-二取代的γ-丁内酯。

  DOI：

  10.1002/adsc.201600427
• 作为产物：
  描述：

  4-cyanochalcone 、 丙二腈 在 potassium fluoride on clinoptilolite 作用下， 以 甲醇 为溶剂， 反应 0.3h， 以93%的产率得到2-(1-(4-cyanophenyl)-3-oxo-3-phenylpropyl)malononitrile
  参考文献：
  名称：

  An active and selective heterogeneous catalytic system for Michael addition

  摘要：

  Potassium fluoride doped natural zeolite was found to be an efficient and selective solid base catalyst for 1,4-Michael addition. The catalyst is easily prepared and the workup procedure simplified by simple filtration. All products were obtained in high yields as well as short reaction times. (C) 2012 Mohammad A. Khalilzadeh. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.02.006

文献信息

• Back to Natural Cinchona Alkaloids: Highly Enantioselective Michael Addition of Malononitrile to Enones
  作者：Alessio Russo、Alessandra Perfetto、Alessandra Lattanzi

  DOI：10.1002/adsc.200900712

  日期：2009.12

  An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy route to difficultly accessible ester derivatives has been also disclosed.

  通过使用奎宁作为有机催化剂，已经开发了将丙二腈向烯酮高效且方便的高对映选择性迈克尔加成反应。以优异的收率和高的不对称诱导率（高达95％ee）分离了加合物。还公开了一种容易获得的酯衍生物的简便方法。
• Visible-Light Driven, Metal-Free Hydroalkylation of Alkenes Mediated by Electron Donor-Acceptor Complex Using Benzothiazolines
  作者：Tatsuhiro Uchikura、Tatsuya Fujii、Kaworuko Moriyama、Takahiko Akiyama

  DOI：10.1246/bcsj.20210322

  日期：2021.12.15

  A visible-light mediated, catalyst-free hydroalkylation of electron-deficient alkenes was achieved using benzothiazoline as a radical transfer reagent. The photoreaction proceeded under household LEDs. Mechanistic studies elucidated the formation of an electron-donor-acceptor complex between benzothiazoline and electron-deficient alkenes.

  以苯并噻唑啉为自由基转移试剂，在可见光介导下实现了缺电子烯烃的无催化剂加氢烷基化反应。光反应在家用 LED 灯下进行。机理研究阐明了苯并噻唑啉和缺电子烯之间形成的电子供体-受体复合物。
• A dynamic kinetic asymmetric transfer hydrogenation–cyclization tandem reaction: an easy access to chiral 3,4-dihydro-2H-pyran-carbonitriles
  作者：Dongsong Zheng、Qiankun Zhao、Xiaoying Hu、Tanyu Cheng、Guohua Liu、Wei Wang

  DOI：10.1039/c7cc02156a

  日期：——

  (mesitylene)RuCl(monosulfonated diamine) catalysed dynamic kinetic resolution (DKR)–asymmetric transfer hydrogenation (ATH) process is developed for highly enantio- (up to 99% ee) and diastereo- (up to 98:2 dr) selective reduction of challenging racemic α-aryl-γ-keto malononitriles. A spontaneous cyclization reaction of the hydrogenation products delivers a cascade process for efficient synthesis of useful enantioenriched

  开发了一种手性（间苯三甲）RuCl（单磺化二胺）催化的动态动力学拆分（DKR）-不对称转移氢化（ATH）工艺，用于高度对映体（高达99％ee）和非对映体（高达98 ：2 dr）的选择性降低具有挑战性的外消旋α-芳基-γ-酮基丙二腈。氢化产物的自发环化反应提供了一种级联过程，用于有效合成有用的对映体富集的3,4-二氢-2 H-吡喃-腈。
• An active and selective heterogeneous catalytic system for Michael addition
  作者：Hoda Keipour、Mohammad A. Khalilzadeh、Abolfazl Hosseini、Afsaneh Pilevar、Daryoush Zareyee

  DOI：10.1016/j.cclet.2012.02.006

  日期：2012.5

  Potassium fluoride doped natural zeolite was found to be an efficient and selective solid base catalyst for 1,4-Michael addition. The catalyst is easily prepared and the workup procedure simplified by simple filtration. All products were obtained in high yields as well as short reaction times. (C) 2012 Mohammad A. Khalilzadeh. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of <i>cis</i> -α,γ-Substituted-γ-Butyrolactones
  作者：Sara Meninno、Chiara Volpe、Alessandra Lattanzi

  DOI：10.1002/adsc.201600427

  日期：2016.9.1

  enantioselective one‐pot synthesis of important building blocks, α‐chiral γ‐keto esters, has been developed by combining a quinine‐catalyzed Michael addition of malononitrile to trans‐enones followed by magnesium monoperoxyphthalate (MMPP) oxidation. These synthons proved to be useful reagents for a simple access to challenging cis‐α,γ‐disubstituted γ‐butyrolactones in good diastereoselectivity and

  通过结合奎宁催化的丙二醛向反式烯酮的迈克尔加成反应以及随后的单过氧邻苯二甲酸镁（MMPP）氧化反应，已经开发出了对映体选择性很强的重要组成部分，α-手性γ-酮酯。这些合成子被证明是有用的试剂，用于以良好的非对映选择性和高对映体控制容易地获得具有挑战性的顺式， α，γ-二取代的γ-丁内酯。