(+)-[(1R,3S)-2,2-dimethyl-3-(2-methyl-1H-indol-3-yl)cyclopropyl]acetic acid | 530100-19-7

• 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: (+)-[(1R,3S)-2,2-dimethyl-3-(2-methyl-1H-indol-3-yl)cyclopropyl]acetic acid
• 英文别名: [(1R,3s)-2,2-dimethyl-3-(2-methyl-1h-indol-3-yl)cyclopropyl]acetic acid；2-[(1R,3S)-2,2-dimethyl-3-(2-methyl-1H-indol-3-yl)cyclopropyl]acetic acid
• CAS: 530100-19-7
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: RMGJBKRIVXPOAA-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 (+)-[(1R,3S)-2,2-dimethyl-3-(2-methyl-1H-indol-3-yl)cyclopropyl]acetic acid 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以88%的产率得到ethyl (+)-[(1R,3S)-2,2-dimethyl-3-(2-methyl-1H-indol-3-yl)cyclopropyl]acetate
  参考文献：
  名称：

  摘要：

  2,2-Dimethyl-3-(2-methyl-3-indolyl)cyclopropylacetic acid, its amide and esters, and the corresponding alcohol, viz., the product of ester reduction by LiAlH4, were synthesized. The chemoselectivity of N- and O-alkylation of these compounds was studied. Selective mono-alkylation at the nitrogen atom of the heterocycle,O-alkylation to the side chain, or dialkylation at both nucleophilic sites can be carried out under conditions of phase-transfer catalysis. The N-acylation at the indole fragment of nitrile of this acid occurs only under the Vilsmeier-Haak formylation conditions.

  DOI：

  10.1023/a:1021392216350
• 作为产物：
  描述：

  (1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 17.0h， 生成 (+)-[(1R,3S)-2,2-dimethyl-3-(2-methyl-1H-indol-3-yl)cyclopropyl]acetic acid
  参考文献：
  名称：

  摘要：

  2,2-Dimethyl-3-(2-methyl-3-indolyl)cyclopropylacetic acid, its amide and esters, and the corresponding alcohol, viz., the product of ester reduction by LiAlH4, were synthesized. The chemoselectivity of N- and O-alkylation of these compounds was studied. Selective mono-alkylation at the nitrogen atom of the heterocycle,O-alkylation to the side chain, or dialkylation at both nucleophilic sites can be carried out under conditions of phase-transfer catalysis. The N-acylation at the indole fragment of nitrile of this acid occurs only under the Vilsmeier-Haak formylation conditions.

  DOI：

  10.1023/a:1021392216350

文献信息

• ——
  作者：E. A. Burakova、O. N. Burchak、A. M. Chibiryaev

  DOI：10.1023/a:1021392216350

  日期：——

  2,2-Dimethyl-3-(2-methyl-3-indolyl)cyclopropylacetic acid, its amide and esters, and the corresponding alcohol, viz., the product of ester reduction by LiAlH4, were synthesized. The chemoselectivity of N- and O-alkylation of these compounds was studied. Selective mono-alkylation at the nitrogen atom of the heterocycle,O-alkylation to the side chain, or dialkylation at both nucleophilic sites can be carried out under conditions of phase-transfer catalysis. The N-acylation at the indole fragment of nitrile of this acid occurs only under the Vilsmeier-Haak formylation conditions.