((S)-1-[(R)-1-phenylethyl]-1,2,3,4-tetrahydrobenzo[h]quinolin-2-yl)methanol | 1252060-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ((S)-1-[(R)-1-phenylethyl]-1,2,3,4-tetrahydrobenzo[h]quinolin-2-yl)methanol
• CAS: 1252060-03-9
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: AKHJCJGOOXNFRC-UZLBHIALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((S)-1-[(R)-1-phenylethyl]-1,2,3,4-tetrahydrobenzo[h]quinolin-2-yl)methanol 在 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 以98%的产率得到(S)-(1,2,3,4-tetrahydrobenzo[h]quinolin-2-yl)methanol
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines

  摘要：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles was successfully achieved via Pd-catalyzed intramolecular C-N bond formation between the nitrogen originated from the aziridine and the halogen containing aromatic carbon. This reaction has a broad substrate scope to provide various enantiomerically pure (3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)methanols, 2-hydroxymethyl-1,2,3,4-tetrahydroquinolines and (1,2,3,4-tetrahydroquinoxalin-2-yl)methanols from common chiral aziridines in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.027
• 作为产物：
  描述：

  (S)-4-(1-bromonaphthalen-2-yl)-2-[(R)-1-phenylethylamino]butan-1-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 以59%的产率得到((S)-1-[(R)-1-phenylethyl]-1,2,3,4-tetrahydrobenzo[h]quinolin-2-yl)methanol
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines

  摘要：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles was successfully achieved via Pd-catalyzed intramolecular C-N bond formation between the nitrogen originated from the aziridine and the halogen containing aromatic carbon. This reaction has a broad substrate scope to provide various enantiomerically pure (3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)methanols, 2-hydroxymethyl-1,2,3,4-tetrahydroquinolines and (1,2,3,4-tetrahydroquinoxalin-2-yl)methanols from common chiral aziridines in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.027