1-benzoyl-2-(4-methylphenyl)-3,3-dicyanocyclopropane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzoyl-2-(4-methylphenyl)-3,3-dicyanocyclopropane
• 英文别名: (2R,3R)-2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1-dicarbonitrile
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: YSAZGRVLCNAWCY-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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-benzoyl-2-(4-methylphenyl)-3,3-dicyanocyclopropane 在 一水合肼 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以69%的产率得到5-phenyl-3-(p-tolyl)-1H-pyrazole
  参考文献：
  名称：

  由2-芳基-3-苯甲酰基-1,1-环丙烷二腈和肼合成5-芳基-3-苯基吡唑的新方法

  摘要：

  实现了合成5-芳基-3-苯基吡唑的新方法。2-芳基-3-苯甲酰基-1，1-环丙烷二腈与肼的区域选择性开环反应在所述方法中起关键作用。

  DOI：

  10.1002/jhet.5570430237
• 作为产物：
  描述：

  2-(4-甲基亚苄基)-丙二腈 、 (2-oxo-2-phenylethyl)triphenylarsonium bromide 在 potassium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 4.0h， 以93%的产率得到1-benzoyl-2-(4-methylphenyl)-3,3-dicyanocyclopropane
  参考文献：
  名称：

  KF·2H2O存在下顺式-1-芳基-2-苯甲酰基-3,3-二氰基环丙烷的立体选择性合成

  摘要：

  摘要 KF·2H2O 是合成顺-1,2-环丙烷与砷盐和烯烃的高效碱。该工艺的优点是反应条件温和、后处理容易、收率高、立体选择性高。

  DOI：

  10.1081/scc-200032500

文献信息

• One-Pot Method for Stereoselective Cyclopropanation of Electron-Deficient Olefins with Methyl Bromoacetate and Phenacyl Bromide in the Presence of Triphenylarsine
  作者：Zhongjiao Ren、Weiguo Cao、Weiyu Ding、Yu Wang

  DOI：10.1055/s-2005-916035

  日期：——

  triphenylarsine-catalyzed one-pot procedure for the preparation of cis-cyclopropanes with acyclic electron-deficient olefins with carbonyl-stabilized arsonium ylides formed from methyl bromoacetate or phenacyl bromide in the presence of NaHCO 3 has been achieved. This method is simple, high-yielding and cis-selective. The success of this method depends on the choice of base solvent and temperature.

  已经实现了一种三苯胂​​催化的一锅法，用于在 NaHCO 3 存在下与由溴乙酸甲酯或苯酰溴形成的羰基稳定的砷叶立德制备具有无环缺电子烯烃的顺式环丙烷。该方法简单、高产且具有顺式选择性。这种方法的成功取决于基础溶剂和温度的选择。
• Stereoselective Synthesis of <i>cis</i>‐1‐Aryl‐2‐benzoyl‐3,3‐dicyanocyclopropanes in the Presence of KF·2H₂O
  作者：Zhongjiao Ren、Weiguo Cao、Weiyu Ding、Yu Wang、Lilin Wang

  DOI：10.1081/scc-200032500

  日期：2004.1.1

  Abstract KF · 2H2O was found to be a highly efficient base for synthesis of cis‐1,2‐cyclopropanes with arsonium salt and olefins. The advantages of the process are mild reaction condition, easy workup, excellent yields, and high stereoselectivity.

  摘要 KF·2H2O 是合成顺-1,2-环丙烷与砷盐和烯烃的高效碱。该工艺的优点是反应条件温和、后处理容易、收率高、立体选择性高。
• A novel synthesis of cyclopropyl lactam and amide from<i>cis</i>-2-aryl-3-benzoyl-1,1-dicynocyclopropane with H₂O₂in the presence of NaHCO₃
  作者：Zhongjiao Ren、Jie Chen、Yeying Lu、Danyi Wu、Weiguo Cao

  DOI：10.1002/jhet.5570440503

  日期：2007.9

  The process for preparation of cyclopropyl lactam and amide from cis-2-aryl-3-benzoyl-1,1-dicynocyclopropane with H2O2 in the Presence of NaHCO3 is described. The highly stereoselective conversion of monocyano group to amide has been carried out in the present method.

  描述了在NaHCO 3存在下由顺式-2-芳基-3-苯甲酰基-1，1-二壬基环丙烷与H 2 O 2制备环丙基内酰胺和酰胺的方法。在本方法中已经进行了单氰基向酰胺的高度立体选择性的转化。
• A new stereoselective approach for the synthesis of substituted 3-cyclopropylmethylene-1,3-dihydro-indol-2-one via the condensation reaction of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes with oxindole in water
  作者：Dong Zhou、Haigang Yu、Ying Liu、Jie Chen、Hongmei Deng、Min Shao、Zhongjiao Ren、Weiguo Cao

  DOI：10.1016/j.tetlet.2010.08.025

  日期：2010.10

  A new stereoselective approach for the synthesis of substituted 3-cyclopropylmethylene-1,3-dihydroindol-2-one via the condensation reaction of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes with oxindole in water was achieved. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Cyclopropanation of Olefins Catalyzed by a Novel<i>C</i>₃-Symmetric Arsine
  作者：Changqing Wang、Yanping Yi、Daoan Xiao、Rong Zhou、Hui Liang、Guangquan Mei

  DOI：10.1080/00397911.2013.817018

  日期：2014.2.16

  A novel C-3-symmetric arsine was employed in the one-pot cyclopropanation of olefins with carbonyl-stabilized arsonium ylides formed in situ from phenacyl bromide in the presence of NaHCO3. This new arsine demonstrates good stereoselectivity and activity in the one-pot cyclopropanation of arylidenemalononitrile. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]