1H-吲哚-3-甲腈,2,3-二氢-2-羰基-3-(2-丙烯基)- | 105600-16-6

• 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
• 中文名称: 1H-吲哚-3-甲腈,2,3-二氢-2-羰基-3-(2-丙烯基)-
• 英文名称: 3-allyl-2-oxoindoline-3-carbonitrile
• 英文别名: 2-oxo-3-prop-2-enyl-1H-indole-3-carbonitrile
• CAS: 105600-16-6
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: CRRATBWSFCKSQU-UHFFFAOYSA-N

物化性质

• 沸点：
  418.2±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氰基吲哚 在 1,4-二甲基哌嗪 、 N-氯代丁二酰亚胺 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1H-吲哚-3-甲腈,2,3-二氢-2-羰基-3-(2-丙烯基)-
  参考文献：
  名称：

  Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones

  摘要：

  In this Article, a strategy to obtain highly enantio-selective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.

  DOI：

  10.1021/jo302039n

文献信息

• KONISHI KEN-ICHI; NISHIGUCHI IKUZO; HIRASHIMA TSUNEAKI, CHEM. EXPRESS, 1,(1986) N 5, 287-290
  作者：KONISHI KEN-ICHI、 NISHIGUCHI IKUZO、 HIRASHIMA TSUNEAKI

  DOI：——

  日期：——
• Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones
  作者：Trung Cao、Elizabeth C. Linton、Joshua Deitch、Simon Berritt、Marisa C. Kozlowski

  DOI：10.1021/jo302039n

  日期：2012.12.21

  In this Article, a strategy to obtain highly enantio-selective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.