1-methyl-3-n-decylindole

• 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: 1-methyl-3-n-decylindole
• 英文别名: 3-decyl-1-methyl-1H-indole；3-Decyl-1-methylindole
• 化学式: C₁₉H₂₉N
• 分子量: 271.446
• InChiKey: RDVOPXQYYSCJIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-碘癸烷 在 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 生成 1-methyl-3-n-decylindole
  参考文献：
  名称：

  Formation of Stable Vesicles from N- or 3-Alkylindoles:  Possible Evidence for Tryptophan as a Membrane Anchor in Proteins

  摘要：

  Twelve indole derivatives have been prepared and studied. Five were 1-substituted: 1, methyl; 2, n-hexyl; 3, n-octyl; 4, n-octadecyl; and 5, cholestanyloxycarbonylmethyl. Four were 3-substituted: 6, methyl; 7, n-hexyl; 8, n-octyl; and 9, n-octadecyl. Three were disubstituted as follows: 10, 1-n-decyl-3-n-decyl; ii, 1-methyl-3-n-decyl; and 12, 1,3-bis(n-octadecyl)indole. Sonication of aqueous suspensions afforded stable aggregates from 3-5 and 8-12. Laser light scattering, dye entrapment, and electron microscopy were used to characterize the aggregates. Aggregates formed from N-substituted indoles proved to be more robust than those formed from 3-alkylindoles. A stable monolayer formed from 3-n-octadecylindole but not from N- or 1,3-disubstituted analogues by using a Langmuir-Blodgett trough. The formation of aggregates was explained in terms of stacking by the relatively polar indole headgroup. In the monolayer experiment, this force was apparently overwhelmed by II-bonding interactions with the aqueous phase.

  DOI：

  10.1021/jo000040l

文献信息

• Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis
  作者：Shota Nomiyama、Takehiro Hondo、Teruhisa Tsuchimoto

  DOI：10.1002/adsc.201500502

  日期：2016.3.31

  By applying carbonyl compounds as sources of alkyl groups to the indium‐catalyzed reductive alkylation of indoles, a reliable and practical method capable of offering a wide range of alkylindoles with structural diversity has been developed. An important feature of this method is that the loading of the indium catalyst can be reduced by more than that of the original alkyne‐based system.

  通过将羰基化合物作为烷基源用于铟催化的吲哚还原烷基化反应，已开发出一种可靠实用的方法，能够提供具有结构多样性的多种烷基吲哚。该方法的一个重要特征是铟催化剂的负载量可以比原始的基于炔烃的系统减少更多。