2-cyano-2-(2-oxoindolin-3-ylidene)acetamide | 601487-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-cyano-2-(2-oxoindolin-3-ylidene)acetamide
• 英文别名: 2-cyano-2-(2-oxo-1H-indol-3-ylidene)acetamide
• CAS: 601487-94-9
• 化学式: C₁₁H₇N₃O₂
• 分子量: 213.195
• InChiKey: SNPYAXJHMCQQFO-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C
• 沸点：
  536.2±50.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-2-(2-oxoindolin-3-ylidene)acetamide 、 乙酰丙酮 在 acylase ‘Amano’ from Aspergillus oryzae 、 乙二醇 作用下， 以 水 为溶剂， 反应 4.0h， 以96%的产率得到5'-acetyl-6'-methyl-2,2'-dioxo-1,2,2',3'-tetrahydro-1'H-spiro[indole-3,4'-pyridine]-3'-carbonitrile
  参考文献：
  名称：

  Diastereoselective synthesis of spirooxindole derivatives via biocatalytic domino reaction

  摘要：

  A facile promiscuous reaction catalyzed by Acylase 'Amano' was developed for the preparation of spirooxindole derivatives. At the optimized reaction condition, the acylase-catalyzed domino reactions could provide a series of different spirooxindole products in moderate yields and good diastereoselectivity. A chemo-enzymatic two-step process was also designed successfully, and several representative spirooxindole derivatives could be obtained in nearly quantitative yields. Additionally, one tentative mechanism for this enzyme-catalyzed process was proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.027
• 作为产物：
  描述：

  2-(2-氧杂环丁-3-亚基)丙二腈 在 甲酸 、 palladium diacetate 作用下， 反应 2.0h， 以45%的产率得到2-cyano-2-(2-oxoindolin-3-ylidene)acetamide
  参考文献：
  名称：

  Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles

  摘要：

  A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions with good to excellent yield.[GRAPHICS].

  DOI：

  10.1080/00397911.2018.1542496

文献信息

• Reaction of Isatins with Active Methylene Compounds on Neutral Alumina: Formation of Knoevenagel Condensates and Other Interesting Products
  作者：Manas Chakrabarty、Ratna Mukherjee、Shiho Arima、Yoshihiro Harigaya

  DOI：10.3987/com-08-11504

  日期：——

  and 5-nitro derivatives underwent smooth reaction with a variety of acyclic and cyclic active methylene compounds on neutral alumina at rt to efficiently furnish Knoevenagel condensates in the majority of the cases and tandem Knoevenagel condensation-Michael addition products including spiro compounds in two cases.

  在大多数情况下，靛红及其 N-甲基和 5-硝基衍生物在中性氧化铝上与多种无环和环状活性亚甲基化合物顺利反应，在大多数情况下有效地提供 Knoevenagel 缩合物和串联的 Knoevenagel 缩合-迈克尔加成产物，包括螺环两种情况下的复合。
• Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
  作者：Yingtian Liu、Xinxin Dang、Yu He、Hudong Bai、Xuehong Chen、Jun-Long Li、Junting Fan、Hezhong Jiang、Jiahong Li

  DOI：10.1080/00397911.2018.1542496

  日期：2019.3.4

  A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions with good to excellent yield.[GRAPHICS].
• Diastereoselective synthesis of spirooxindole derivatives via biocatalytic domino reaction
  作者：Yi-Ru Liang、Xiao-Yang Chen、Qi Wu、Xian-Fu Lin

  DOI：10.1016/j.tet.2014.12.027

  日期：2015.1

  A facile promiscuous reaction catalyzed by Acylase 'Amano' was developed for the preparation of spirooxindole derivatives. At the optimized reaction condition, the acylase-catalyzed domino reactions could provide a series of different spirooxindole products in moderate yields and good diastereoselectivity. A chemo-enzymatic two-step process was also designed successfully, and several representative spirooxindole derivatives could be obtained in nearly quantitative yields. Additionally, one tentative mechanism for this enzyme-catalyzed process was proposed. (C) 2014 Elsevier Ltd. All rights reserved.