2-(1-Benzo[1,3]dioxol-5-yl-3-oxo-3-phenyl-propyl)-malononitrile | 199390-81-3

• 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-Benzo[1,3]dioxol-5-yl-3-oxo-3-phenyl-propyl)-malononitrile
• 英文别名: Propanedinitrile, [1-(1,3-benzodioxol-5-yl)-3-oxo-3-phenylpropyl]-；2-[1-(1,3-benzodioxol-5-yl)-3-oxo-3-phenylpropyl]propanedinitrile
• CAS: 199390-81-3
• 化学式: C₁₉H₁₄N₂O₃
• 分子量: 318.332
• InChiKey: ZEAADEUPLNSMLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-溴代肉桂醛 、 2-(1-Benzo[1,3]dioxol-5-yl-3-oxo-3-phenyl-propyl)-malononitrile 在 2-均三甲苯基-2,5,6,7-四氢吡咯并[2,1-C][1,2,4]三唑-4-鎓氯化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 rac-(3'R,5'S)-5'-(benzo[d][1,3]dioxol-5-yl)-5',6'-dihydro-[1,1':3',1''-terphenyl]-4',4'(3'H)-dicarbonitrile
  参考文献：
  名称：

  通过N-杂环碳烯催化的迈克尔加合物的高对映选择性动力学拆分：环己烯的高效不对称路线

  摘要：

  使用手性N-杂环卡宾催化剂实现了迈克尔加合物动力学拆分的高效策略。动力学拆分提供了一条新的便捷途径，可以以高收率和高对映异构体过量（高达99％ee，选择性因子高达458）获得环己烯和迈克尔加合物的单一非对映异构体。这种“两只苍蝇一拍打”的概念允许通过一次转换同时合成这两种具有合成价值的化合物类别。

  DOI：

  10.1002/chem.201802420
• 作为产物：
  描述：

  (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylprop-2-en-1-one 、 丙二腈 在 potassium fluoride on basic alumina 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以57%的产率得到2-(1-Benzo[1,3]dioxol-5-yl-3-oxo-3-phenyl-propyl)-malononitrile
  参考文献：
  名称：

  A Convenient Synthesis of (3-Oxo-1,3-diaryl) Propylpropanedinitrile Catalyzed by Kf-Alumina

  摘要：

  A series of (3-oxo-1,3-diaryl) propylpropanedinitriles were synthesized by Michael addition reaction of chalcones and malononitriles in the presence of potassium fluoride on alumina.

  DOI：

  10.1080/00397919808004960

文献信息

• Samarium(II) iodide promoted novel reductive coupling reactions of ketones and nitriles
  作者：Longhu Zhou、Yongmin Zhang、Daqing Shi

  DOI：10.1016/s0040-4039(98)01984-4

  日期：1998.11

  The intramolecular and intermolecular reductive coupling reaction of ketones-nitriles promoted by SmI2 were studied.

  研究了SmI 2促进的酮腈的分子内和分子间还原偶联反应。
• Samarium(II) Iodide-Promoted Intermolecular and Intramolecular Ketone-Nitrile Reductive Coupling Reactions
  作者：Longhu Zhou、Yongmin Zhang、Daqing Shi

  DOI：10.1055/s-2000-6220

  日期：——

  Samarium(II) iodide, a strong one-electron transfer reducing reagent, has been successfully utilized for the intermolecular and intramolecular reductive coupling reactions of ketones with nitriles. α-Hydroxy ketones, monocyclic, fused bicyclic α-hydroxy ketones and monocyclic α-amino alcohols composed of a number of substitution patterns have been prepared in good yields at room temperature or reflux under neutral conditions. The procedure can avoid overreduction of the resulting of α-hydroxy ketones or α-amino alcohols. The crystal structures of monocyclic α-amino alcohols are reported.

  钐（II）碘化物是一种强的一电子转移还原试剂，已成功用于酮类与腈类的分子间和分子内还原偶联反应。在室温或回流的中性条件下，已经制备了多种取代模式的α-羟基酮、单环和融合双环的α-羟基酮以及单环的α-氨基醇，产率良好。该方法能够避免生成的α-羟基酮或α-氨基醇的过度还原。还报告了单环α-氨基醇的晶体结构。
• 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。
• Ma, Yongmin; Zhang, Yongmin, Journal of Chemical Research - Part S, 2002, # 6, p. 288 - 290
  作者：Ma, Yongmin、Zhang, Yongmin

  DOI：——

  日期：——
• Intermolecular and Intramolecular Ketone–Nitrile Reductive Coupling Reactions Promoted by TiCl4–Sm System
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1016/s0040-4020(00)00077-6

  日期：2000.5

  The intermolecular and intramolecular reductive coupling reactions of ketones with nitriles have been successfully promoted by low-valent titanium prepared by the TiCl4-Sm system. Substituted ketones, monocyclic alpha-amino alcohols and monocyclic amines composed of a number of substitution patterns have been prepared in good yields at room or THF reflux temperature under neutral conditions. The procedure can avoid over reduction of the resulting of ketones, alpha-amino alcohols or amines. The crystal structures of two monocyclic alpha-amino alcohols are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.