(S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide | 1238365-88-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• 英文别名: (S)-N-((S)-1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide；(S)-N-[(S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide；(3S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• CAS: 1238365-88-2
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: ZJIUNFXZNFHXCE-GUYCJALGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到(S)-1-phenyl-N-(((S)-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl)ethanamine
  参考文献：
  名称：

  Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation

  摘要：

  The use of the tetrahydroisoquinoline scaffold is well documented in biologically active compounds. However, reports of the utilisation of tetrahydroisoquinoline compounds in asymmetric catalysis are limited. The synthesis of novel diamine ligands possessing the tetrahydroisoquinoline (tetrahydroisoquinoline) backbone and evaluation of their activity in the asymmetric transfer hydrogenation of acetophenone are presented. The diamine ligands in conjunction with i-PrOH as the hydrogen source and [RhCl2(Cp*)](2) as the metal precursor proved to be the most effective of the tetrahydroisoquinoline derivatives for this catalytic system. Water was found to have a profound influence on the enantioselectivity of the reaction. Optimisation of the amount water, i-PrOH and catalytic loading content rendered the best result of 70% enantioselectivity for the (S)-1-phenylethanol isomer product. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.017
• 作为产物：
  描述：

  S-1,2,3,4-四氢异喹啉-3-羧酸苄酯盐酸盐 在 5%-palladium/activated carbon 、 氢气 、 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、5.0 kPa 条件下， 反应 44.17h， 生成 (S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and Characterization of N-Substituted (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxamides and Thioamides as Organocatalysts for Asymmetric Aldol Reaction

  摘要：

  DOI：

  10.3987/com-14-13029

文献信息

• Tetrahydroisoquinoline-Based N-Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes
  作者：Tricia Naicker、Per I. Arvidsson、Hendrik G. Kruger、Glenn E. M. Maguire、Thavendran Govender

  DOI：10.1002/ejoc.201100923

  日期：2011.12

  The short synthesis of a series of novel chiral N-oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α-β-unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are the first of their kind based on the tetrahydroisoquinoline framework. The chiral homoallyl products were obtained with good chemical efficiency

  报道了一系列新型手性 N-氧化物有机催化剂的短合成及其在芳烃和 α-β-不饱和醛与烯丙基三氯硅烷的不对称烯丙基化反应中的评价。这些易于改性的有机催化剂是基于四氢异喹啉骨架的同类有机催化剂中的第一个。在温和的反应条件 (23 °C) 下，以良好的化学效率（高达 93% 的产率）和高对映选择性（高达 91% ee）获得了手性高烯丙基产物。
• [3,3]‐Sigmatropic Rearrangements of Naphthyl 1‐Propargyl Ethers: <i>para</i> ‐Propargylation and Catalytic Asymmetric Dearomatization
  作者：Lifeng Wang、Yuqiao Zhou、Zhishan Su、Fengcai Zhang、Weidi Cao、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/anie.202211785

  日期：2022.12.23

  naphthyl 1-propargyl ethers through para-Claisen rearrangement was described, and chirality transfer was observed. Moreover, the enantioselective dearomatization of C4-substituted substrates was realized by using a chiral N,N′-dioxide/CoII complex catalyst. The DFT calculations and experimental results support the ortho-Claisen rearrangement/Cope rearrangement sequence process.

  描述了 C4-未取代的萘基 1-炔丙基醚通过对位克莱森重排进行的形式热对位 -C(sp 2 )-H 炔丙基化，并观察到手性转移。此外，C4 取代底物的对映选择性脱芳构化是通过使用手性N,N'-二氧化物/Co II络合物催化剂实现的。DFT 计算和实验结果支持邻-Claisen 重排/Cope 重排序列过程。
• Synthesis and Characterization of N-Substituted (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxamides and Thioamides as Organocatalysts for Asymmetric Aldol Reaction
  作者：Pavel Drabina、Ladislav Androvič、Illia Panov、Lydie Harmand、Zdeňka Padělková、Miloš Sedlák

  DOI：10.3987/com-14-13029

  日期：——
• Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation
  作者：Byron K. Peters、Sai Kumar Chakka、Tricia Naicker、Glenn E.M. Maguire、Hendrik G. Kruger、Pher G. Andersson、Thavendran Govender

  DOI：10.1016/j.tetasy.2010.04.017

  日期：2010.4

  The use of the tetrahydroisoquinoline scaffold is well documented in biologically active compounds. However, reports of the utilisation of tetrahydroisoquinoline compounds in asymmetric catalysis are limited. The synthesis of novel diamine ligands possessing the tetrahydroisoquinoline (tetrahydroisoquinoline) backbone and evaluation of their activity in the asymmetric transfer hydrogenation of acetophenone are presented. The diamine ligands in conjunction with i-PrOH as the hydrogen source and [RhCl2(Cp*)](2) as the metal precursor proved to be the most effective of the tetrahydroisoquinoline derivatives for this catalytic system. Water was found to have a profound influence on the enantioselectivity of the reaction. Optimisation of the amount water, i-PrOH and catalytic loading content rendered the best result of 70% enantioselectivity for the (S)-1-phenylethanol isomer product. (C) 2010 Elsevier Ltd. All rights reserved.