(S)-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline | 608525-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-(3',4'-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline；(S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline；(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline
• CAS: 608525-32-2
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: FYJFAAHVQJERQQ-INIZCTEOSA-N

物化性质

• 沸点：
  450.0±30.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline 、 碘甲烷 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (-)-cuspareine
  参考文献：
  名称：

  A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (−)-cuspareine

  摘要：

  A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (-)-cuspareine via enantiospecific construction of the (R)-benzyl 2-formyl-3,4-dihydroquinoline-1(2H)-carboxylate. We have achieved an efficient enantiospecific synthesis of (-)-cuspareine starting from known key starting materials. The reactions employed for individual transformations are simple and high yielding, and the strategy could potentially be easily extended. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.023
• 作为产物：
  描述：

  4-羟基喹啉 在 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 mineral oil 为溶剂， 反应 38.33h， 生成 (S)-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Cu(I)-Catalyzed Alkynylation of Quinolones

  摘要：

  DOI：

  10.1021/acs.orglett.2c00020

文献信息

• Enantioselective Syntheses of Tetrahydroquinolines Based on Iridium-Catalyzed Allylic Substitutions: Total Syntheses of (+)-Angustureine and (-)-Cuspareine
  作者：Gedu Satyanarayana、Daniel Pflästerer、Günter Helmchen

  DOI：10.1002/ejoc.201100981

  日期：2011.12

  preparation of tetrahydroquinolines has been developed. The procedure involves a highly regio-and enantioselective intermolecular iridium-catalyzed allylic amination followed by one-pot hydroboration and intramolecular Suzuki-Miyaura cross-coupling. This method was applied in total syntheses of the alkaloids (+)-angustureine and (-)-cuspareine.

  已开发出一种用于制备四氢喹啉的无保护基团的两步法。该过程涉及高度区域和对映选择性的分子间铱催化烯丙基胺化，然后是一锅硼氢化和分子内 Suzuki-Miyaura 交叉偶联。该方法应用于生物碱(+)-茴香碱和(-)-cuspareine的全合成。
• Synthesis of Electronically Deficient Atropisomeric Bisphosphine Ligands and Their Application in Asymmetric Hydrogenation of Quinolines
  作者：Min-Can Wang、Yong-Gui Zhou、De-Yang Zhang、Duo-Sheng Wang、Chang-Bin Yu、Kai Gao

  DOI：10.1055/s-0030-1260129

  日期：2011.9

  atropisomeric bisphos­phine ligands have been synthesized from (S)-MeO-BiPhep. The introduction­ of electron-withdrawing groups in the ligands had a dramatic influence on both the enantioselectivity and the activity of catalyst. The iridium complex of the MeO-BiPhep-based ligand bearing a trifluoromethanesulfonyl group was successfully applied in the asymmetric hydrogenation of quinolines with ee values of up

  从（S）-MeO-BiPhep合成了一系列电子缺陷的阻转异构双膦配体。配体中吸电子基团的引入对催化剂的对映选择性和活性均具有显着影响。具有三氟甲磺酰基的MeO-BiPhep基配体的铱配合物已成功应用于ee值高达95％和周转数（TON）高达14,600的喹啉的不对称氢化中。 铱-不对称氢化-缺电子配体-喹啉
• Manganese‐Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π–π Interaction**
  作者：Chenguang Liu、Mingyang Wang、Shihan Liu、Yujie Wang、Yong Peng、Yu Lan、Qiang Liu

  DOI：10.1002/anie.202013540

  日期：2021.3

  The non‐noble metal‐catalyzed asymmetric hydrogenation of N‐heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asymmetric hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97 % ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which is competitive with the activity

  报道了非贵金属催化的N-杂芳族化合物喹啉的不对称氢化。一种新型手性钳式锰催化剂在喹啉的不对称氢化中表现出出色的催化活性，提供了高收率和对映选择性（高达97％ee）。在低催化剂负载量（S / C = 4000）下，达到了3840的周转率，与该反应中最有效的贵金属催化剂的活性相竞争。对映选择性的精确调节通过π-π相互作用来保证。
• Asymmetric Hydrogenation with Water/Silane as the Hydrogen Source
  作者：Da-Wei Wang、Duo-Sheng Wang、Qing-An Chen、Yong-Gui Zhou

  DOI：10.1002/chem.200902790

  日期：2010.1.25

  Water as a hydride source: A new pathway to form metal–hydride bonds has been developed through the reaction of easily available metal–silyl compounds with water. This method has been successfully applied to asymmetric hydrogenation of heteroaromatic compounds with up to 93 % ee under mild autoclave‐free conditions (see scheme).

  水作为氢化物来源：通过容易获得的金属-甲硅烷基化合物与水反应，已开发出形成金属-氢化物键的新途径。该方法已成功应用于温和的无高压灭菌条件下，ee高达93％ee的杂芳族化合物的不对称加氢 反应（参见方案）。
• Asymmetric hydrogenation of quinolines activated by Brønsted acids
  作者：Duo-Sheng Wang、Yong-Gui Zhou

  DOI：10.1016/j.tetlet.2010.04.004

  日期：2010.6

  Enantioselective hydrogenation of quinolines and quinoxalines catalyzed by iridium/diphosphine complex with catalytic amount of Brønsted acid as activator was developed. In the presence of piperidine·TfOH as the activator, full conversions and up to 92% ee were obtained.

  开发了铱/二膦配合物催化量的布朗斯台德酸作为活化剂催化的喹啉和喹喔啉的对映选择性加氢反应。在哌啶·TfOH作为活化剂的存在下，获得了全部转化率和高达92％的ee。