2-[1-(Methoxymethyl)-5,7-dimethyl-2-oxoindol-3-ylidene]propanedinitrile | 1454790-60-3

• 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-[1-(Methoxymethyl)-5,7-dimethyl-2-oxoindol-3-ylidene]propanedinitrile
• 英文别名: 2-[1-(methoxymethyl)-5,7-dimethyl-2-oxoindol-3-ylidene]propanedinitrile
• CAS: 1454790-60-3
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: IGKZSTVLBGPLEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(Methoxymethyl)-5,7-dimethyl-2-oxoindol-3-ylidene]propanedinitrile 、 4-苯基-3-丁炔-2-酮 在 三(4-氟苯基)磷化氢 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以80%的产率得到(E)-3-benzylidene-1'-(methoxymethyl)-5',7'-dimethyl-2',4-dioxospiro[cyclopentane-1,3'-indoline]-2,2-dicarbonitrile
  参考文献：
  名称：

  Stereoselective Synthesis of Five-Membered Spirooxindoles through Tomita Zipper Cyclization

  摘要：

  Functionalized five-membered spirooxindoles were furnished in good yields and excellent stereoselectivities by using an effective Tomita zipper cyclization (TZC) reaction through organophosphine catalysis.

  DOI：

  10.1021/ol4020305

文献信息

• Divergent Cyclization Reactions of Morita–Baylis–Hillman Carbonates of 2-Cyclohexenone and Isatylidene Malononitriles
  作者：Jing Peng、Guang-Yao Ran、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.5b02157

  日期：2015.9.18

  Zwitterionic dienolates generated from Morita-Baylis-Hillman carbonates of cyclohexen-2-one and a phenolic tertiary amine catalyst underwent divergent cyclization reactions with isatylidene malononitriles. A new [4 + 2] stepwise cyclization process was disclosed to deliver complex bridged spirooxindoles after the initial delta'-regioselective Rauhut-Currier-type reaction with N-methyl electrophiles by the catalysis of beta-isocupreidine, while spirooxindoles incorporating an aromatic chromene motif were generated with N-MOM acceptors in the presence of alpha-isocupreine through different domino transformations.
• Stereoselective Synthesis of Five-Membered Spirooxindoles through Tomita Zipper Cyclization
  作者：D. B. Ramachary、Chintalapudi Venkaiah、Patoju M. Krishna

  DOI：10.1021/ol4020305

  日期：2013.9.20

  Functionalized five-membered spirooxindoles were furnished in good yields and excellent stereoselectivities by using an effective Tomita zipper cyclization (TZC) reaction through organophosphine catalysis.