(1R,3S)-benzyl 3-((R)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1240163-18-1

• 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: (1R,3S)-benzyl 3-((R)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• 英文别名: (1R,3S)-benzyl 3-((S)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate；benzyl (1R,3S)-3-[[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamoyl]-6,7-dimethoxy-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1240163-18-1
• 化学式: C₃₁H₃₆N₂O₆
• 分子量: 532.637
• InChiKey: VYGDVZQAFNSFSW-UWPQIUOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3S)-benzyl 3-((R)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(1R,3S)-benzyl 3-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
  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
• 作为产物：
  描述：

  L-缬氨醇 、 (1R,3S)-2-(benzyloxycarbonyl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到(1R,3S)-benzyl 3-((R)-1-hydroxy-3-methylbutan-2-ylcarbamoyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
  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.