methyl 2-(5-ethoxy-5-oxopentyl)-1H-indole-5-carboxylate | 1318759-47-5

• 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: methyl 2-(5-ethoxy-5-oxopentyl)-1H-indole-5-carboxylate
• CAS: 1318759-47-5
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: KIRIYVWXZQFTAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴戊酸乙酯 、 吲哚-5-甲酸甲酯 在 双(乙腈)氯化钯(II) 、 norbornene 、 水 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 14.0h， 以87%的产率得到methyl 2-(5-ethoxy-5-oxopentyl)-1H-indole-5-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation

  摘要：

  A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C-H activation process at the indole ring, which features high regioselectivity and excellent functional group, tolerance. The reaction represents the first example for a generally applicable, direct C-H alkylation of indole at the 2-position.

  DOI：

  10.1021/ja2055066

文献信息

• Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation
  作者：Lei Jiao、Thorsten Bach

  DOI：10.1021/ja2055066

  日期：2011.8.24

  A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C-H activation process at the indole ring, which features high regioselectivity and excellent functional group, tolerance. The reaction represents the first example for a generally applicable, direct C-H alkylation of indole at the 2-position.
• Regioselective Direct C–H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process
  作者：Thorsten Bach、Lei Jiao

  DOI：10.1055/s-0033-1338523

  日期：——

  Nitrogen-containing heterocycles, including 1H-indoles and electron-deficient 1H-pyrroles, undergo a palladium/norbornene-cocatalyzed regioselective alkylation at the C-H bond adjacent to the NH group. A primary alkyl halide is used as the electrophile and the reaction proceeds smoothly under mild conditions to give 2-alkyl-1H-indoles and 2-substituted or 2,3-disubstituted 5-alkyl-1H-pyrroles in good yields.