(-)-(S)-2-(3'-benzyloxy-4'-methoxyphenethyl)-1,2,3,4-tetrahydroquinoline | 696664-23-0

• 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'-benzyloxy-4'-methoxyphenethyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: (S)-2-(3'-benzyloxy-4'-methoxyphenethyl)-1,2,3,4-tetrahydroquinoline；(2S)-2-[2-(4-methoxy-3-phenylmethoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline
• CAS: 696664-23-0
• 化学式: C₂₅H₂₇NO₂
• 分子量: 373.495
• InChiKey: YJFICLISOQIBIA-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 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'-benzyloxy-4'-methoxyphenethyl)-1,2,3,4-tetrahydroquinoline 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 11.0h， 生成 (S)-N(1)-methyl-2-[2′-(3″-hydroxy-4″-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  The enantioselective total synthesis of alkaloid (−)-galipeine

  摘要：

  The first total synthesis of (-)-galipeine was accomplished in seven steps with 54% overall yield from isovanillin based on Ir-catalyzed asymmetric hydrogenation of a quinoline derivative as a key step, with its absolute stereochemistry being established. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.012
• 作为产物：
  描述：

  3-苄氧基-4-甲氧苄醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 吡啶 、 正丁基锂 、 氢气 、 碘 、 三溴化磷 、 (R)-(+)-(6,6′-二甲氧联苯-2,2′-二基)双(二苯基膦) 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 2.0h， 生成 (-)-(S)-2-(3'-benzyloxy-4'-methoxyphenethyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  The enantioselective total synthesis of alkaloid (−)-galipeine

  摘要：

  The first total synthesis of (-)-galipeine was accomplished in seven steps with 54% overall yield from isovanillin based on Ir-catalyzed asymmetric hydrogenation of a quinoline derivative as a key step, with its absolute stereochemistry being established. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.012

文献信息

• 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
• The enantioselective total synthesis of alkaloid (−)-galipeine
  作者：Peng-Yu Yang、Yong-Gui Zhou

  DOI：10.1016/j.tetasy.2004.02.012

  日期：2004.4

  The first total synthesis of (-)-galipeine was accomplished in seven steps with 54% overall yield from isovanillin based on Ir-catalyzed asymmetric hydrogenation of a quinoline derivative as a key step, with its absolute stereochemistry being established. (C) 2004 Elsevier Ltd. All rights reserved.