(S)-benzyl 3-(2,6-dimethylphenylcarbamoyl)-3,4-dihydro-isoquinoline-2(1H)-carboxylate | 1383448-90-5

• 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: (S)-benzyl 3-(2,6-dimethylphenylcarbamoyl)-3,4-dihydro-isoquinoline-2(1H)-carboxylate
• 英文别名: benzyl (3S)-3-[(2,6-dimethylphenyl)carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1383448-90-5
• 化学式: C₂₆H₂₆N₂O₃
• 分子量: 414.504
• InChiKey: HDGDHSJHQAEVMI-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 3-(2,6-dimethylphenylcarbamoyl)-3,4-dihydro-isoquinoline-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 3.0h， 以91%的产率得到(S)-N-(2,6-dimethylphenyl)-1,2,3,4-tetrahydroisoquinoline-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
• 作为产物：
  描述：

  3,4-二氢一异喹啉-2,3-二甲酸-2-苄酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (S)-benzyl 3-(2,6-dimethylphenylcarbamoyl)-3,4-dihydro-isoquinoline-2(1H)-carboxylate
  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

文献信息

• Asymmetric conjugate addition of thioglycolate to a range of chalcones using tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands
  作者：Sai Kumar Chakka、Zamani E.D. Cele、Sphelele C. Sosibo、Vivian Francis、Per I. Arvidsson、Hendrik G. Kruger、Glenn E.M. Maguire、Thavendran Govender

  DOI：10.1016/j.tetasy.2012.04.010

  日期：2012.4

  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.