3-bromo-3-((ethoxycarbonyl)methyl)-1-methylindol-2-one | 158589-22-1

• 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: 3-bromo-3-((ethoxycarbonyl)methyl)-1-methylindol-2-one
• CAS: 158589-22-1
• 化学式: C₁₃H₁₄BrNO₃
• 分子量: 312.163
• InChiKey: OSIRBZSSVBMJJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-bromo-3-((ethoxycarbonyl)methyl)-1-methylindol-2-one 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 9.0h， 以84%的产率得到ethyl (E)-2-(1-methyl-2-oxoindolin-3-ylidene)acetate
  参考文献：
  名称：

  Dimerization of a 3-Substituted Oxindole at C-3 and Its Application to the Synthesis of (.+-.)-Folicanthine

  摘要：

  The dimerization of an oxindole in good yield at C-3 to form a benzylic quaternary carbon-carbon bond is described. A radical anion chain mechanism is proposed for the reaction. The dimeric product is transformed into (+/-)-folicanthine by a series of reductions. A crystalline bis-borane complex of (+/-)-folicanthine was obtained, and its molecular structure was determined by X-ray crystallography.

  DOI：

  10.1021/ja00100a010
• 作为产物：
  描述：

  ethyl 2-(1-methyl-2-oxoindolin-3-yl)acetate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 7.0h， 以90%的产率得到3-bromo-3-((ethoxycarbonyl)methyl)-1-methylindol-2-one
  参考文献：
  名称：

  Dimerization of a 3-Substituted Oxindole at C-3 and Its Application to the Synthesis of (.+-.)-Folicanthine

  摘要：

  The dimerization of an oxindole in good yield at C-3 to form a benzylic quaternary carbon-carbon bond is described. A radical anion chain mechanism is proposed for the reaction. The dimeric product is transformed into (+/-)-folicanthine by a series of reductions. A crystalline bis-borane complex of (+/-)-folicanthine was obtained, and its molecular structure was determined by X-ray crystallography.

  DOI：

  10.1021/ja00100a010

文献信息

• Dimerization of a 3-Substituted Oxindole at C-3 and Its Application to the Synthesis of (.+-.)-Folicanthine
  作者：Cheng-Lin Fang、Stephen Horne、Nicholas Taylor、Russell Rodrigo

  DOI：10.1021/ja00100a010

  日期：1994.10

  The dimerization of an oxindole in good yield at C-3 to form a benzylic quaternary carbon-carbon bond is described. A radical anion chain mechanism is proposed for the reaction. The dimeric product is transformed into (+/-)-folicanthine by a series of reductions. A crystalline bis-borane complex of (+/-)-folicanthine was obtained, and its molecular structure was determined by X-ray crystallography.