N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine | 220926-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine
• 英文别名: tert-butyl N-(4-chlorobutyl)-N-[(E)-3-phenylprop-2-enyl]carbamate
• CAS: 220926-88-5
• 化学式: C₁₈H₂₆ClNO₂
• 分子量: 323.863
• InChiKey: KDQUKKGEANXIHR-FMIVXFBMSA-N

物化性质

• 沸点：
  436.7±44.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine 在 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 鹰爪豆碱 作用下， 以 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 反应 11.5h， 生成 N-Boc-L-哌啶-2-羧酸
  参考文献：
  名称：

  Asymmetric Syntheses of N-Boc 2-Substituted Pyrrolidines and Piperidines by Intramolecular Cyclization

  摘要：

  Asymmetric lithiation-substitutions by n-BuLi/(-)-sparteine with the N-Boc-N-(3-halopropyl)allylamines 1-4 provide the N-Boc-2-alkenylpyrrolidines (S)-5, (S)-6, and (S)-7 in yields of 31-93% with enantiomeric ratios (ers) from 65:35 to 90:10. These reactions are shown to involve an initial asymmetric deprotonation, but the enantiodetermining step is a subsequent asymmetric cyclization under the influence of the chiral ligand. Extension to formation of a piperidine is illustrated by reaction of N-Boc-(4-chlorobutyl)cinnamylamine (9) to afford (S)-N-Boc-2-(trans-beta-styryl)piperidine ((S)-10) in 68% yield with an enantiomeric ratio (er) of 84:16. Analogous reactions with epoxide ring openings of N-Boc-N-(oxaalkenyl)benzylamines 11 and 12 afford the corresponding N-Boc-2-phenyl-3-(hydroxymethyl)pyrrolidine (13) in 67% yield with a diastereomeric ratio (dr) of 50:50 and ers of 97:3 and 95:5 and the corresponding N-Boc-2-phenyl-3-(hydroxymethyl)piperidine (14) in 29% yield with a dr of 86:14 and ers of 81:19 and 86:14.

  DOI：

  10.1021/jo981553j
• 作为产物：
  描述：

  2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 29.75h， 生成 N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine
  参考文献：
  名称：

  Asymmetric Syntheses of N-Boc 2-Substituted Pyrrolidines and Piperidines by Intramolecular Cyclization

  摘要：

  Asymmetric lithiation-substitutions by n-BuLi/(-)-sparteine with the N-Boc-N-(3-halopropyl)allylamines 1-4 provide the N-Boc-2-alkenylpyrrolidines (S)-5, (S)-6, and (S)-7 in yields of 31-93% with enantiomeric ratios (ers) from 65:35 to 90:10. These reactions are shown to involve an initial asymmetric deprotonation, but the enantiodetermining step is a subsequent asymmetric cyclization under the influence of the chiral ligand. Extension to formation of a piperidine is illustrated by reaction of N-Boc-(4-chlorobutyl)cinnamylamine (9) to afford (S)-N-Boc-2-(trans-beta-styryl)piperidine ((S)-10) in 68% yield with an enantiomeric ratio (er) of 84:16. Analogous reactions with epoxide ring openings of N-Boc-N-(oxaalkenyl)benzylamines 11 and 12 afford the corresponding N-Boc-2-phenyl-3-(hydroxymethyl)pyrrolidine (13) in 67% yield with a diastereomeric ratio (dr) of 50:50 and ers of 97:3 and 95:5 and the corresponding N-Boc-2-phenyl-3-(hydroxymethyl)piperidine (14) in 29% yield with a dr of 86:14 and ers of 81:19 and 86:14.

  DOI：

  10.1021/jo981553j