3-methyl-1-phenethyl-1H-indole | 1570062-18-8

• 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-methyl-1-phenethyl-1H-indole
• CAS: 1570062-18-8
• 化学式: C₁₇H₁₇N
• 分子量: 235.329
• InChiKey: COFIQVYSBCPUQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  3-methyl-1-phenethylindoline 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 tert-butylperoxy 2-ethylhexyl carbonate 作用下， 以 乙腈 为溶剂， 以44 %的产率得到3-methyl-1-phenethyl-1H-indole
  参考文献：
  名称：

  具有替代断开的 N-芳基吲哚的催化合成。望远镜反应序列的氢氨基烷基化

  摘要：

  报道了对 C3-甲基-N-芳基二氢吲哚和吲哚产物的三催化伸缩合成。原位生成的脲酸钽(V)催化剂用于邻氯苯乙烯与N-甲基苯胺的氢氨基烷基化反应，首先形成C sp 3 ─C sp 3键。随后的镍催化 C-N 偶联形成N-芳基二氢吲哚，如果需要，随后可以使用催化 [Cu(MeCN) 4 ]BF 4和叔氧化成N-芳基吲哚-丁基过氧-2-乙基己基碳酸酯作为末端氧化剂。该策略突出了用于合成吲哚的替代 C-C 键断开，这是通过原子经济的氢化氨基烷基化反应实现的。使用三步两锅法简化该方法，以提供高达 73% 的各种取代的 C3-甲基-N-芳基吲哚的总分离产率。

  DOI：

  10.1021/acs.orglett.2c02510

文献信息

• Olefin-Oriented Selective Synthesis of Linear and Branched N-Alkylated Heterocycles by Hydroamination
  作者：Sushmita、Trapti Aggarwal、Kapil Mohan Saini、Akhilesh K. Verma

  DOI：10.1002/ejoc.202000373

  日期：2020.6.16

  Selective base‐Mediated hydroamination of N‐heterocycles with olefins for the construction of Linear and branched N‐alkylated heterocycles is described. This protocol provided the synthesis of exclusive N‐alkylated product instead of the C‐3 Michael addition product.

  描述了N-杂环与烯烃的选择性碱介导加氢胺化反应，用于构建直链和支链N-烷基化杂环。该协议提供了专有的N-烷基化产物而不是C-3 Michael加成产物的合成。
• Palladium-Catalysed Dehydrogenative Generation of Imines from Amines. A Nature-Inspired Route to Indoles<i>via</i>Cross-Couplings of Amines with Arylhydrazines
  作者：Maurizio Taddei、Manuel G. Mura、Suvi Rajamäki、Lidia De Luca、Andrea Porcheddu

  DOI：10.1002/adsc.201300559

  日期：2013.10.11

  AbstractH‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.magnified image