(S)-2-((1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-4-phenyl-4,5-dihydrooxazole | 1240163-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (S)-2-((1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-4-phenyl-4,5-dihydrooxazole
• 英文别名: (4S)-2-[(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 1240163-36-3
• 化学式: C₂₆H₂₆N₂O₃
• 分子量: 414.504
• InChiKey: HXDYCTIKQYCNOV-SGIRGMQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,3S)-benzyl 6,7-dimethoxy-1-phenyl-3-((S)-4-phenyl-4,5-dihydrooxazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以53%的产率得到(S)-2-((1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-4-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis of tetrahydroisoquinoline (TIQ)–oxazoline ligands and their application in enantioselective Henry reactions

  摘要：

  A novel family of eleven new tetrahydroisoquinoline (TIQ)-oxazoline intermediates and five corresponding copper(II) catalysts has been developed and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide beta-hydroxy nitroalkanes in high conversion (>99%) This paper describes the synthesis of the TIQ compounds from L-dihydroxyphenylalanine (L-DOPA) as the starting material The chiral ligands were complexed in situ with various transition metals such as Cu, Sc, Co, Zn, Ni and Mn and tested as a chiral catalyst for the Henry reaction The reaction was optimized in terms of the metal, counter ion, solvent, temperature and over a range of substrates The corresponding catalyst with copper(II) acetate and 2-propanol as the solvent provides the best enantioselectivities (up to 77% ee) of the corresponding nitroalcohol for 4-chlorobenzaldehyde (C) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.053

文献信息

• Synthesis of tetrahydroisoquinoline (TIQ)–oxazoline ligands and their application in enantioselective Henry reactions
  作者：Rahul B. Kawthekar、Sai Kumar Chakka、Vivian Francis、Pher G. Andersson、Hendrik G. Kruger、Glenn E.M. Maguire、Thavendran Govender

  DOI：10.1016/j.tetasy.2010.04.053

  日期：2010.4

  A novel family of eleven new tetrahydroisoquinoline (TIQ)-oxazoline intermediates and five corresponding copper(II) catalysts has been developed and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide beta-hydroxy nitroalkanes in high conversion (>99%) This paper describes the synthesis of the TIQ compounds from L-dihydroxyphenylalanine (L-DOPA) as the starting material The chiral ligands were complexed in situ with various transition metals such as Cu, Sc, Co, Zn, Ni and Mn and tested as a chiral catalyst for the Henry reaction The reaction was optimized in terms of the metal, counter ion, solvent, temperature and over a range of substrates The corresponding catalyst with copper(II) acetate and 2-propanol as the solvent provides the best enantioselectivities (up to 77% ee) of the corresponding nitroalcohol for 4-chlorobenzaldehyde (C) 2010 Elsevier Ltd All rights reserved.