N-[(1S)-1-(2-iodophenyl)ethyl]-N-isopropyl-2-chloroquinoline-3-carboxamide | 832096-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[(1S)-1-(2-iodophenyl)ethyl]-N-isopropyl-2-chloroquinoline-3-carboxamide
• 英文别名: 2-chloro-N-[(1S)-1-(2-iodophenyl)ethyl]-N-propan-2-ylquinoline-3-carboxamide
• CAS: 832096-89-6
• 化学式: C₂₁H₂₀ClIN₂O
• 分子量: 478.76
• InChiKey: AVCXRQZAJOTZCW-AWEZNQCLSA-N

物化性质

• 熔点：
  94 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  579.8±50.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(1S)-1-(2-iodophenyl)ethyl]-N-isopropyl-2-chloroquinoline-3-carboxamide 在 dibromobis(triphenylphosphine)nickel(II) 四乙基碘化铵 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以64%的产率得到(5S)-5-methyl-6-propan-2-yl-5H-quinolino[3,2-d][2]benzazepin-7-one
  参考文献：
  名称：

  Preparation of axially chiral quinolinium salts related to NAD+ models: new investigations of these biomimetic models as ‘chiral amide-transferring agents’

  摘要：

  The general purpose of this work is to investigate the potential of biomimetic NAD(+) models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD(+) analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlander approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.004
• 作为产物：
  描述：

  2-氯喹啉 在 草酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 N-[(1S)-1-(2-iodophenyl)ethyl]-N-isopropyl-2-chloroquinoline-3-carboxamide
  参考文献：
  名称：

  Preparation of axially chiral quinolinium salts related to NAD+ models: new investigations of these biomimetic models as ‘chiral amide-transferring agents’

  摘要：

  The general purpose of this work is to investigate the potential of biomimetic NAD(+) models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD(+) analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlander approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.004