1-dodecyl-1H-indole | 89590-64-7

• 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: 1-dodecyl-1H-indole
• 英文别名: N-(dodecyl)indole；N-dodecylindole；1H-Indole, 1-dodecyl-；1-dodecylindole
• CAS: 89590-64-7
• 化学式: C₂₀H₃₁N
• 分子量: 285.473
• InChiKey: SHOVGCMSECPWIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-dodecyl-1H-indole 在 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 40.0h， 生成 (1-dodecyl-1H-indol-3-yl)-N,N,N-trimethylmethanaminium iodide
  参考文献：
  名称：

  Synthesis and evaluation of N1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands

  摘要：

  In this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine B (1), a metabolite isolated from the marine bryozoan Flustra foliacea L. The syntheses were carried out using standard methodologies and in good yields. The molecules were tested for their affinities for the alpha 4 beta 2*, alpha 3 beta 4*, alpha 7* and (alpha 1)(2)beta 1 gamma delta nicotinic acetylcholine receptor (nAChR) sub-types. Binding assays showed that, among these ligands, compound 7c exhibited the highest affinity with K-i = 136.1, 93.9 and 862.4 nM for the alpha 4 beta 2*, alpha 3 beta 4*, and alpha 7* nAChRs subtypes, respectively. These results indicated that the indole core might be a useful scaffold for the development of new potent and selective nAChR ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.050
• 作为产物：
  描述：

  1-dodecanoyl-indole-2,3-dione 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到1-dodecyl-1H-indole
  参考文献：
  名称：

  用[BH 3 .THF]配合物还原N-酰基赖氨酸

  摘要：

  通过在室温下用新鲜制备的BH 3还原，可以将N-酰基赖氨酸直接高产率地转化为N-烷基吲哚。THF配合物。该还原代表制备具有长链烷基，特别是那些在碳链内具有卤素的N-烷基吲哚的替代方法。

  DOI：

  10.1016/0040-4039(94)88390-4

文献信息

• Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst
  作者：S. M. A. Hakim Siddiki、Kenichi Kon、Ken-ichi Shimizu

  DOI：10.1039/c4gc01419g

  日期：——

  (H+-exchanged BEA zeolite) is found to be an effective and reusable heterogeneous catalyst for regioselective N-alkylation of indoles with primary aliphatic and benzylic alcohols under additive-free conditions driven by the borrowing-hydrogen methodology. Structural and mechanistic studies suggest a cooperative mechanism of the Pt0 site on Pt metal clusters and the Brønsted acid site of the zeolite,

  负载铂的HBEA（H +交换的BEA沸石）被发现是一种有效且可重复使用的非均相催化剂，用于在借用氢方法的驱动下在无添加剂的条件下用脂肪族和苄基伯醇对吲哚进行区域选择性N-烷基化。结构和机理研究表明，Pt金属簇上的Pt 0位点和沸石的Brønsted酸位点是一种协同机制，其中Pt 0位点负责脱氢/氢化步骤，而Brønsted酸位点负责区域选择性缩合将带有醛的吲哚制成烯胺中间体。
• 9,10-Bis(N-alkylindole-3-yl-vinyl-2)anthracenes as a new series of alkyl length-dependent piezofluorochromic aggregation-induced emission homologues
  作者：Q. K. Sun、W. Liu、S. A. Ying、L. L. Wang、S. F. Xue、W. J. Yang

  DOI：10.1039/c5ra12969a

  日期：——

  AIE active 9,10-bis(N-alkylindole-3-yl-vinyl-2)anthracene homologues (IACn) could be facilely prepared and exhibit alkyl length-dependent piezofluorochromic properties whose spectral shifts increase with the decrease of N-alkyl chain lengths.

  AIE活性9,10-双(-烷基吲哚-3-基-乙烯基-2)蒽同类物(IACn)可以容易地制备，并展现出与烷基链长相关的压致发光性质，其光谱位移随着-烷基链长的减少而增加。
• TBHP Mediated Substrate Controlled Oxidative Dearomatization of Indoles to C2/C3-Quaternary Indolinones
  作者：Jagatheeswaran Kothandapani、Singarajanahalli Mundarinti Krishna Reddy、Subbiah Thamotharan、Shankar Madan Kumar、Kullaiah Byrappa、Subramaniapillai Selva Ganesan

  DOI：10.1002/ejoc.201800167

  日期：2018.6.15

  An efficient metal‐free oxidative dearomatization reaction of indoles is reported for the synthesis of diverse C2/C3‐quaternary indolinones. The nature of the substituent on the indole nitrogen atom dictates the type of product formed in the reaction.

  据报道，吲哚能有效地进行无金属氧化脱芳香化反应，从而合成各种C2 / C3季吲哚啉酮。吲哚氮原子上取代基的性质决定了反应中形成的产物的类型。
• The application of ultrasound to the n-alkylation of amines using phase transfer catalysis
  作者：R.Stephen Davidson、Ali M. Patel、Ali Safdar、David Thornthwaite

  DOI：10.1016/s0040-4039(00)94235-7

  日期：1983.1

  The application of ultrasound to the N-alkylation of a variety of amines by alkyl halides under phase transfer conditions (polyethylene glycol methyl ether and alkylammonium compounds as catalysts) leads to a decrease in the time required to effect reaction.

  在相转移条件下（聚乙二醇甲基醚和烷基铵化合物作为催化剂）将超声波应用于烷基卤化物使各种胺的N-烷基化反应可减少反应所需的时间。
• Directly Bridging Indoles to 3,3′-Bisindolylmethanes by Using Carboxylic Acids and Hydrosilanes under Mild Conditions
  作者：Chang Qiao、Xiao-Fang Liu、Hong-Chen Fu、Hao-Peng Yang、Zhi-Bo Zhang、Liang-Nian He

  DOI：10.1002/asia.201800766

  日期：2018.9.17

  (BIMs) synthesis by reductive alkylation of indoles at the C3 position with carboxylic acids in the presence of hydrosilane was developed for the first time. Instead of aldehydes, more readily available, stable, and easy‐to‐handle carboxylic acids have been employed as alternative alkylating agents. As an efficient organocatalyst, B(C6F5)3 enables the reductive alkylation of various substituted indole

  首次开发了一种简单的路易斯酸促进的3,3'-二吲哚基甲烷（BIM）合成方法，该方法是在存在氢硅烷的情况下，通过羧酸在C3位的吲哚还原烷基化来合成3,3'-二吲哚基甲烷（BIM）。代替醛，更容易获得，稳定和易于处理的羧酸已被用作替代烷基化剂。作为有效的有机催化剂，B（C 6 F 5）3使在室温下和在纯净条件下，各种取代的吲哚衍生物与羧酸进行还原性烷基化反应，收率可达98％。这种无金属的策略为将吲哚直接用羧酸直接官能化为BIM提供了另一种方法，该方案允许将羧酸选择性还原为醛，并形成C-C键。