N-(2-(6-methoxy-1H-indol-3-yl)ethyl)prop-2-en-1-amine | 189681-63-8

• 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: N-(2-(6-methoxy-1H-indol-3-yl)ethyl)prop-2-en-1-amine
• 英文别名: N-[2-(6-methoxy-1H-indol-3-yl)ethyl]prop-2-en-1-amine
• CAS: 189681-63-8
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: LNDXIRMHUPRAOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(6-methoxy-1H-indol-3-yl)ethyl)prop-2-en-1-amine 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 (4aR,13bS,14aS)-11-Methoxy-3,4,4a,5,7,8,13,13b,14,14a-decahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
  参考文献：
  名称：

  A One-Pot Tandem Pictet-Spengler-Diels-Alder Synthesis of Apoyohimbines from 3-Carbomethoxy-2-(formylmethyl)-3-sulfolene

  摘要：

  Pictet-Spengler reactions were carried out between 3-carbomethoxy-2-(formylmethyl)-3-sulfolene and tryptamines. Without isolation, the products were converted with complete stereoselectivity into apoyohimbine derivatives, via sulfur dioxide extrusion followed by intramolecular Diels-Alder cyclisation. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00547-9
• 作为产物：
  描述：

  (6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 N-(2-(6-methoxy-1H-indol-3-yl)ethyl)prop-2-en-1-amine
  参考文献：
  名称：

  A One-Pot Tandem Pictet-Spengler-Diels-Alder Synthesis of Apoyohimbines from 3-Carbomethoxy-2-(formylmethyl)-3-sulfolene

  摘要：

  Pictet-Spengler reactions were carried out between 3-carbomethoxy-2-(formylmethyl)-3-sulfolene and tryptamines. Without isolation, the products were converted with complete stereoselectivity into apoyohimbine derivatives, via sulfur dioxide extrusion followed by intramolecular Diels-Alder cyclisation. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00547-9

文献信息

• Self-Relay Gold(I)-Catalyzed Pictet-Spengler/Cyclization Cascade Reaction for the Rapid Elaboration of Pentacyclic Indole Derivatives
  作者：Valérian Gobé、Pascal Retailleau、Xavier Guinchard

  DOI：10.1002/chem.201503941

  日期：2015.12.1

  Gold‐catalyzed cascade reactions allow the rapid elaboration of pentacyclic indolo[2,3‐a]quinolizidines from N‐allyl tryptamines and ortho‐alkynylarylaldehydes. The tandem process combines a gold‐catalyzed Pictet‐Spengler reaction and a cyclization occurring concomitantly with an allyl transfer from the nitrogen atom to the stilbene function. Various substituted allyls were successfully transferred

  金催化的级联反应可快速合成N-烯丙基色胺和邻炔基芳基醛中的五环吲哚[2,3- a ]喹唑烷。串联过程结合了金催化的Pictet-Spengler反应和伴随从氮原子到二苯乙烯官能团的烯丙基转移而发生的环化反应。成功地转移了各种取代的烯丙基，从而提供了高非对映选择性的典型产物，产率为60-98％。带有丁烯醇链的色胺在高非对映选择性下会进一步环化成手性半胱氨酸。
• Gold(I)-Catalyzed Carboaminations of Allenes by <i>N</i> -Allyltetrahydro-β-carbolines: An Experimental and Theoretical Study
  作者：Valérian Gobé、Maxime Dousset、Pascal Retailleau、Vincent Gandon、Xavier Guinchard

  DOI：10.1002/adsc.201601075

  日期：2016.12.22

  N‐Allyltetrahydro‐β‐carbolines bearing a pendant allene undergo unprecedented gold(I)‐catalyzed cyclizations proceeding with an allyl migration from the nitrogen to the allene moiety. The initial product of the gold‐catalyzed cyclization evolves either via isomerization or Cope rearrangement, leading to different scaffolds. Density function theory (DFT) calculations established that the allyl migration

  具有烯丙基侧基的N-烯丙基四氢-β-咔啉经历了空前的金（I）催化环化反应，烯丙基从氮迁移到烯丙基部分。金催化环化的初始产物通过异构化或Cope重排进化而来，从而形成不同的支架。密度泛函理论（DFT）计算确定烯丙基迁移以异步表面方式发生。
• A One-Pot Tandem Pictet-Spengler-Diels-Alder Synthesis of Apoyohimbines from 3-Carbomethoxy-2-(formylmethyl)-3-sulfolene
  作者：John Leonard、Andrew B Hague、Martin F Jones

  DOI：10.1016/s0040-4039(97)00547-9

  日期：1997.4

  Pictet-Spengler reactions were carried out between 3-carbomethoxy-2-(formylmethyl)-3-sulfolene and tryptamines. Without isolation, the products were converted with complete stereoselectivity into apoyohimbine derivatives, via sulfur dioxide extrusion followed by intramolecular Diels-Alder cyclisation. (C) 1997 Published by Elsevier Science Ltd.