(3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-o-tolyl-1,2,3,4-tetra-hydroisoquinoline-3-carboxamide) | 1383448-95-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-o-tolyl-1,2,3,4-tetra-hydroisoquinoline-3-carboxamide)
• CAS: 1383448-95-0
• 化学式: C₃₇H₄₀N₄O₂
• 分子量: 572.75
• InChiKey: SDQNNLFFSLDVIA-PXLJZGITSA-N

物化性质

• 沸点：
  793.4±60.0 °C(Predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.68
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-o-tolyl-1,2,3,4-tetra-hydroisoquinoline-3-carboxamide) 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以66%的产率得到(3S,3'S)-2,2'-(propane-1,3-diyl)bis(3-(o-tolylcarbamoyl)-1,2,3,4-tetrahydroisoquinoline 2-oxide)
  参考文献：
  名称：

  Asymmetric conjugate addition of thioglycolate to a range of chalcones using tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands

  摘要：

  A series of novel TIQ based N,N'-oxide ligands were synthesised and screened for their catalytic activity in the enantioselective conjugate addition of thioglycolate to chalcones. Bulky groups on the side chain of the TIQ backbone provided the highest enantioselectivity of up to 88% with 10 mol % catalyst loading. It was also observed that these reactions proceeded optimally in the presence of dichloromethane as a solvent. Screening of various metals emphasized La(OTf)(3) as the ideal pre-catalyst for this particular reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.010
• 作为产物：
  描述：

  3,4-二氢一异喹啉-2,3-二甲酸-2-苄酯 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 (3S,3'S)-2,2'-(propane-1,3-diyl)bis(N-o-tolyl-1,2,3,4-tetra-hydroisoquinoline-3-carboxamide)
  参考文献：
  名称：

  Asymmetric conjugate addition of thioglycolate to a range of chalcones using tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands

  摘要：

  A series of novel TIQ based N,N'-oxide ligands were synthesised and screened for their catalytic activity in the enantioselective conjugate addition of thioglycolate to chalcones. Bulky groups on the side chain of the TIQ backbone provided the highest enantioselectivity of up to 88% with 10 mol % catalyst loading. It was also observed that these reactions proceeded optimally in the presence of dichloromethane as a solvent. Screening of various metals emphasized La(OTf)(3) as the ideal pre-catalyst for this particular reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.010