[1-(2-naphthalenyl)-3-oxo-3-phenyl-1-propyl]propanedinitrile | 368447-50-1

• 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: [1-(2-naphthalenyl)-3-oxo-3-phenyl-1-propyl]propanedinitrile
• 英文别名: 2-(1-(naphthalen-2-yl)-3-oxo-3-phenylpropyl)malononitrile；2-[1-(2-Naphthyl)-3-oxo-3-phenyl-propyl]propanedinitrile；2-(1-naphthalen-2-yl-3-oxo-3-phenylpropyl)propanedinitrile
• CAS: 368447-50-1
• 化学式: C₂₂H₁₆N₂O
• 分子量: 324.382
• InChiKey: MEFWHUSARDJKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-(2-naphthalenyl)-3-oxo-3-phenyl-1-propyl]propanedinitrile 在 溴 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 2-(4-morpholinyl)-4-(2-naphthalenyl)-6-phenyl-3-pyridinecarbonitrile
  参考文献：
  名称：

  Barsoum, Flora F.; Hussein, Manal M.M., Bollettino Chimico Farmaceutico, 2002, vol. 141, # 3, p. 181 - 187

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-naphthalenyl)-1-phenylprop-2-en-1-one 、 丙二腈 在 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 [1-(2-naphthalenyl)-3-oxo-3-phenyl-1-propyl]propanedinitrile
  参考文献：
  名称：

  光催化多功能共价有机框架的构建

  摘要：

  报道了一种光活性TAPA−BPy−COF及其金属化Pd@TAPA−BPy−COF ，它们都可以作为光催化应用中高效的可重复使用的光催化剂。

  DOI：

  10.1002/chem.202303497

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。
• 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。
• Stereoselective reductive radical cyclization of ketonitriles catalyzed by Cp2TiCl2 in the presence of chlorosilane and zinc
  作者：Longhu Zhou、Toshikazu Hirao

  DOI：10.1016/s0040-4020(01)00645-7

  日期：2001.8

  Reductive radical cyclization of ketonitriles was catalyzed by Cp2TiCl2 in the presence of Me3SiCl, zinc powder and imidazole, giving the 2-amino-3-cyano-2-cyclopenten-1-ols in moderate to good yields with high trans selectivity (up to 94% trans). The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereoselectivity of the cyclized products was

  酮腈的还原性自由基环化物通过的Cp催化2的TiCl 2在我的存在3的SiCl，锌粉和咪唑，在温和给予2-氨基-3-氰基-2-环戊烯-1-醇，以良好的产率具有高反式选择性（最高94％反式）。详细研究了催化剂，氯硅烷，助还原剂，溶剂和温度对环化产物收率和非对映选择性的影响。
• In vitro antifungal evaluation and structure–activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall
  作者：Silvia N López、Marı́a V Castelli、Susana A Zacchino、José N Domı́nguez、Gricela Lobo、Jaime Charris-Charris、Juan C.G Cortés、Juan C Ribas、Cristina Devia、Ana M Rodrı́guez、Ricardo D Enriz

  DOI：10.1016/s0968-0896(01)00116-x

  日期：2001.8

  Here we report the synthesis, in vitro antifungal evaluation and SAR study of 41 chalcones and analogues. In addition, all active structures were tested for their capacity of inhibiting Saccharomyces cerevisiae beta (1,3)-glucan synthase and chitin synthase, enzymes that catalyze the synthesis of the major polymers of the fungal cell wall. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.