N-(2-(1,2-dimethyl-1H-indol-3-yl)ethyl)acetamide | 1353013-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-(1,2-dimethyl-1H-indol-3-yl)ethyl)acetamide
• 英文别名: N-[2-(1,2-dimethyl-1H-indol-3-yl)ethyl]acetamide；N-[2-(1,2-dimethylindol-3-yl)ethyl]acetamide
• CAS: 1353013-73-6
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: ZMPIHDMNPVXEET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-(1,2-dimethyl-1H-indol-3-yl)ethyl)acetamide 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以61%的产率得到N-(2-(2-formyl-1-methyl-1H-indol-3-yl)ethyl)acetamide
  参考文献：
  名称：

  A one-pot three-component reaction for the preparation of highly functionalized tryptamines

  摘要：

  We have developed a general one-pot method to provide highly functionalized tryptamine derivatives, via a Fischer indole type pathway. In this article, we demonstrate optimal conditions for a one-pot indole synthesis, allowing for the synthesis of a broad scope of 2-methyl tryptamine derivatives and a precursor for the synthesis of the core structure of some akuammiline alkaloids. Additionally, further modification of the indole products is described. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.11.032
• 作为产物：
  描述：

  2-甲基吡咯啉 在 4-二甲氨基吡啶 、 水 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 25.25h， 生成 N-(2-(1,2-dimethyl-1H-indol-3-yl)ethyl)acetamide
  参考文献：
  名称：

  A one-pot three-component reaction for the preparation of highly functionalized tryptamines

  摘要：

  We have developed a general one-pot method to provide highly functionalized tryptamine derivatives, via a Fischer indole type pathway. In this article, we demonstrate optimal conditions for a one-pot indole synthesis, allowing for the synthesis of a broad scope of 2-methyl tryptamine derivatives and a precursor for the synthesis of the core structure of some akuammiline alkaloids. Additionally, further modification of the indole products is described. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.11.032

文献信息

• Synthesis of Tryptamine Derivatives via a Direct, One-Pot Reductive Alkylation of Indoles
  作者：Marika Righi、Francesca Topi、Silvia Bartolucci、Annalida Bedini、Giovanni Piersanti、Gilberto Spadoni

  DOI：10.1021/jo3010028

  日期：2012.7.20

  An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several

  报道了在TES / TFA存在下用N-保护的氨基乙基缩醛对吲哚进行有效的一锅还原烷基化反应。它代表了从吲哚和氮官能化的缩醛直接合成色胺的首个通用方法。这种融合和通用的方法使用安全且便宜的试剂，可在温和条件下进行，并可以耐受多个官能团。该新方法可有效地用于Luzindole（一种参考MT2选择性褪黑激素受体拮抗剂）和褪黑素的克级合成。