3-(1-methylheptyl)-1H-indole | 19224-95-4

• 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: 3-(1-methylheptyl)-1H-indole
• 英文别名: 3-(1-Methylheptyl)indole；3-octan-2-yl-1H-indole
• CAS: 19224-95-4
• 化学式: C₁₆H₂₃N
• 分子量: 229.365
• InChiKey: FWZDVJCOZDSYOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(1-methylheptyl)-1H-indole 以72%的产率得到
  参考文献：
  名称：

  KOST A. N.; BUDYLIN V. A.; MOCHALOVA O. A., BECTH. MOSK. YH-TA. XIMIYA , 1975, 16, HO 4, 467-471

  摘要：

  DOI：
• 作为产物：
  描述：

  2-octan-2-yl-1H-indole;(2S)-2-[(2,4,5,7-tetranitrofluoren-9-ylidene)amino]oxypropanoic acid 以67%的产率得到
  参考文献：
  名称：

  KOST A. N.; BUDYLIN V. A.; MOCHALOVA O. A., BECTH. MOSK. YH-TA. XIMIYA , 1975, 16, HO 4, 467-471

  摘要：

  DOI：

文献信息

• Ruthenium Pincer Complex Catalyzed Selective Synthesis of C‐3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols
  作者：Nandita Biswas、Rahul Sharma、Dipankar Srimani

  DOI：10.1002/adsc.202000326

  日期：2020.7.29

  catalyst for C‐3 alkylation of 1H‐indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C‐3 alkylated indoles directly from 2‐(2‐nitrophenyl)ethan‐1‐ol

  在此，我们介绍了Ru-SNS配合物，该配合物可作为1H-吲哚与各种脂族伯醇和仲醇（包括环状醇以及苄醇）的C-3烷基化的有用催化剂。仅通过改变反应参数，就可以从同一组吲哚和醇中选择性地合成双吲哚基甲烷衍生物。此外，据报道，直接由2-（2-硝基苯基）乙-1-醇和Ru-络合物通过“借用氢”策略催化的醇可持续合成C-3烷基化的吲哚。该协议提供了一种原子经济的可持续途径，可用于访问结构上重要的化合物，如金刚烷，颤敏A和色胺基衍生物。
• Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols
  作者：Anggi Eka Putra、Kei Takigawa、Hatsuki Tanaka、Yoshihiko Ito、Yohei Oe、Tetsuo Ohta

  DOI：10.1002/ejoc.201300744

  日期：2013.10

  Pd/C and RuCl2(PPh3)3/DPEphos effectively catalyzed the alkylation of indole with alcohols to give 3‐substituted indoles selectively. Various types of substrates were examined and were found to give the corresponding 3‐substituted indoles in up to 99 % yield. Under different reaction conditions, RuCl2(PPh3)3/DPEphos catalyzed the selective formation of bis(3‐indolyl)phenylmethane derivatives.

  Pd / C和RuCl 2（PPh 3）3 / DPEphos有效地催化了吲哚与醇的烷基化反应，从而选择性地生成了3个取代的吲哚。检查了各种类型的底物，发现它们以高达99％的产率提供了相应的3-取代的吲哚。在不同的反应条件下，RuCl 2（PPh 3）3 / DPEphos催化了双（3-吲哚基）苯基甲烷衍生物的选择性形成。
• 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。
• Nickel-catalyzed C3-alkylation of indoles with alcohols <i>via</i> a borrowing hydrogen strategy
  作者：Miao Hu、Yong Jiang、Nan Sun、Baoxiang Hu、Zhenlu Shen、Xinquan Hu、Liqun Jin

  DOI：10.1039/d1nj01581h

  日期：——

  An efficient Ni-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen pathway was achieved utilizing an N,O-donor coordinated nickel complex as the precatalyst.

  通过借氢途径利用N,O-供体配位的镍配合物作为预催化剂，实现了一种高效的Ni催化的醇与吲哚的C3烷基化。
• Reductive Alkylation of Indoles with Alkynes and Hydrosilanes under Indium Catalysis
  作者：Teruhisa Tsuchimoto、Mitsutaka Kanbara

  DOI：10.1021/ol1029673

  日期：2011.3.4

  Under Indium catalysis, diverse alkylindoles were successfully prepared with a flexible combination of indoles and alkynes in the presence of hydrosilanes. In addition to the hydrosilane, carbon nucleophiles are also available. This new method generates alkylindoles in yields over 70% with a broad scope of functional group compatibility.

  在铟催化下，在氢化硅烷存在下，吲哚和炔烃的灵活组合成功制备了各种烷基吲哚。除了氢硅烷以外，还可以使用碳亲核试剂。这种新方法可产生烷基吲哚，收率超过70％，并具有广泛的官能团相容性。