2-[3-(5-Bromo-indol-1-yl)-3-oxo-propyl]-malonic acid dimethyl ester | 913534-09-5

• 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-[3-(5-Bromo-indol-1-yl)-3-oxo-propyl]-malonic acid dimethyl ester
• CAS: 913534-09-5
• 化学式: C₁₆H₁₆BrNO₅
• 分子量: 382.211
• InChiKey: YYUNCRJXXXPRDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[3-(5-Bromo-indol-1-yl)-3-oxo-propyl]-malonic acid dimethyl ester 在 manganese triacetate 作用下， 以 甲醇 为溶剂， 以68%的产率得到2-Bromo-6-oxo-7,8-dihydro-6H-pyrido[1,2-a]indole-9,9-dicarboxylic acid dimethyl ester
  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 2-[3-(5-Bromo-indol-1-yl)-3-oxo-propyl]-malonic acid dimethyl ester
  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

• An Aluminum Triflate-Catalyzed Intramolecular Reaction Sequence Toward Concise Construction of the Tetrahydropyrido[1,2-<i>a</i>]indol-6-one Skeleton
  作者：Jun-Jiao Wang、An-Xi Zhou、Gang-Wei Wang、Shang-Dong Yang

  DOI：10.1002/adsc.201400391

  日期：2014.11.3

  AbstractAn aluminum triflate‐catalyzed intramolecular reaction sequence involving protonation and Mannich‐like nucleophilic addition of indoles toward the concise construction of the tetrahydropyrido[1,2‐a]indol‐6‐one skeleton is reported. This new reaction pattern employs a carbon atom as nucleophile to form a CC bond which bears one or even two quaternary carbons and leads to the dearomatization of indoles with high atom economy.magnified image