2-[1-(2,4-Dichloro-phenyl)-3-oxo-3-phenyl-propyl]-malononitrile | 94360-04-0

• 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-(2,4-Dichloro-phenyl)-3-oxo-3-phenyl-propyl]-malononitrile
• 英文别名: 2-[1-(2,4-Dichlorophenyl)-3-oxo-3-phenylpropyl]malononitrile；2-[1-(2,4-dichlorophenyl)-3-oxo-3-phenylpropyl]propanedinitrile
• CAS: 94360-04-0
• 化学式: C₁₈H₁₂Cl₂N₂O
• 分子量: 343.212
• InChiKey: LKOYBKGXZNMEHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-[1-(2,4-Dichloro-phenyl)-3-oxo-3-phenyl-propyl]-malononitrile 在 溴 、 potassium acetate 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以96%的产率得到2-bromo-2-[1-(2,4-dichlorophenyl)-3-oxo-3-phenylpropyl]propanedinitrile
  参考文献：
  名称：

  Shestopalov, A. M.; Promonenkov, V. K.; Sharanin, Yu. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1382 - 1401

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-[1-(2,4-Dichloro-phenyl)-3-oxo-3-phenyl-propyl]-malononitrile
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00116-x

文献信息

• Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes
  作者：Xiang-Yu Chen、Sun Li、Qiang Liu、Mukesh Kumar、Anssi Peuronen、Kari Rissanen、Dieter Enders

  DOI：10.1002/chem.201802420

  日期：2018.7.11

  A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N‐heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with high enantiomeric excesses (up to 99 % ee with a selectivity factor of up to 458). This “two flies with one swat” concept allows the

  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。
• One-Pot Cascade Heterocyclization of γ- and β-Ketomalononitriles to 2,4-Dichloro-Substituted Pyrano[2,3-<i>d</i>]pyrimidines and Furo[2,3-<i>d</i>]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide
  作者：Zhen-Hua Li、Zhi-Jiang Jiang、Qiao-Ling Shao、Jin-Jing Qin、Qiang-Feng Shu、Wen-Hao Lu、Wei-Ke Su

  DOI：10.1021/acs.joc.8b00669

  日期：2018.6.15

  A one-pot cascade heterocyclization strategy has been developed for the synthesis of 2,4-dichloro-substituted pyrano[2,3-d]pyrimidines and furo[2,3-d]pyrimidines from linear γ- and β-ketomalononitriles using triphosgene and triphenylphosphine oxide. The reaction afforded synthetic useful products with moderate to good yields, bypassing the conventional harsh conditions of chlorination. The mechanistic

  已开发出一锅级联杂环化策略，使用三光气从线性γ-和β-酮基乙腈合成2,4-二氯取代的吡喃并[2,3- d ]嘧啶和呋喃并[2,3- d ]嘧啶和三苯基氧化膦。该反应绕开了常规的苛刻氯化条件，提供了具有中等至良好收率的合成有用产物。机理研究表明反应是通过非异氰酸酯途径进行的，第二步可能以三苯膦氧化物催化的方式进行。