Dimethyl 2-[3-[3-(cyanomethyl)indol-1-yl]-3-oxopropyl]propanedioate | 913534-10-8

• 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: Dimethyl 2-[3-[3-(cyanomethyl)indol-1-yl]-3-oxopropyl]propanedioate
• CAS: 913534-10-8
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: MJUKPMQURCKIJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-[3-[3-(cyanomethyl)indol-1-yl]-3-oxopropyl]propanedioate 在 manganese triacetate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以72%的产率得到Dimethyl 10-(cyanomethyl)-6-oxo-7,8-dihydropyrido[1,2-a]indole-9,9-dicarboxylate
  参考文献：
  名称：

  Expanding the Scope of Mn(OAc)₃-Mediated Cyclizations:  Synthesis of the Tetracyclic Core of Tronocarpine

  摘要：

  Pyrroles, indoles, and surprisingly, indolines, when equipped with a pendant malonyl group on the nitrogen atom, were effective substrates in a Mn(III)-mediated oxidative cyclization reaction, yielding the 1,2-annulated products in good to excellent yields. When indole acetonitrile was used as a substrate this method provided a rapid synthesis of a tetracyclic tronocarpine subunit.

  DOI：

  10.1021/ol061698+
• 作为产物：
  描述：

  2-(methoxycarbonyl)pentanedioic acid 1-methyl ester 在 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 Dimethyl 2-[3-[3-(cyanomethyl)indol-1-yl]-3-oxopropyl]propanedioate
  参考文献：
  名称：

  Expanding the Scope of Mn(OAc)₃-Mediated Cyclizations:  Synthesis of the Tetracyclic Core of Tronocarpine

  摘要：

  Pyrroles, indoles, and surprisingly, indolines, when equipped with a pendant malonyl group on the nitrogen atom, were effective substrates in a Mn(III)-mediated oxidative cyclization reaction, yielding the 1,2-annulated products in good to excellent yields. When indole acetonitrile was used as a substrate this method provided a rapid synthesis of a tetracyclic tronocarpine subunit.

  DOI：

  10.1021/ol061698+

文献信息

• Expanding the Scope of Mn(OAc)₃-Mediated Cyclizations:  Synthesis of the Tetracyclic Core of Tronocarpine
  作者：Jakob Magolan、Michael A. Kerr

  DOI：10.1021/ol061698+

  日期：2006.9.1

  Pyrroles, indoles, and surprisingly, indolines, when equipped with a pendant malonyl group on the nitrogen atom, were effective substrates in a Mn(III)-mediated oxidative cyclization reaction, yielding the 1,2-annulated products in good to excellent yields. When indole acetonitrile was used as a substrate this method provided a rapid synthesis of a tetracyclic tronocarpine subunit.