N-(tert-butoxycarbonyl)-N-(4-oxa-4-pentenyl)benzylamine | 154874-92-7

• 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-oxa-4-pentenyl)benzylamine
• 英文别名: Carbamic acid, (3-oxiranylpropyl)(phenylmethyl)-, 1,1-dimethylethyl ester；tert-butyl N-benzyl-N-[3-(oxiran-2-yl)propyl]carbamate
• CAS: 154874-92-7
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: JFXNVLRJCXEWEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N-(4-oxa-4-pentenyl)benzylamine 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到2-Phenyl-3-(hydroxymethyl)piperidine
  参考文献：
  名称：

  Intramolecular Cyclizations of .alpha.-Lithioamine Synthetic Equivalents: Convenient Syntheses of 3-, 5-, and 6-Membered-Ring Heterocyclic Nitrogen Compounds and Elaborations of 3-Membered Ring Systems

  摘要：

  A lithiation-intramolecular cyclization reaction of N-Boc chloroalkyl secondary amines is reported to provide the 2-aryl-substituted pyrrolidine and piperidines 6, 7, 9, and 11 and a series of 2-azabicyclo[3.1.0] derivatives 14-25, including cyclopropane derivatives of proline and of the indolizidine-pyrrolizidine alkaloid ring system. Lithiation-substitutions of N-Boc-N-ethylcyclopropylamine to give 27-29 and lithiation-silylations of N-Boc aziridines to give 31-33 also are reported.

  DOI：

  10.1021/jo00081a002
• 作为产物：
  描述：

  tert-butyl benzyl(pent-4-en-1-yl)carbamate 在 间氯过氧苯甲酸 作用下， 生成 N-(tert-butoxycarbonyl)-N-(4-oxa-4-pentenyl)benzylamine
  参考文献：
  名称：

  Intramolecular Cyclizations of .alpha.-Lithioamine Synthetic Equivalents: Convenient Syntheses of 3-, 5-, and 6-Membered-Ring Heterocyclic Nitrogen Compounds and Elaborations of 3-Membered Ring Systems

  摘要：

  A lithiation-intramolecular cyclization reaction of N-Boc chloroalkyl secondary amines is reported to provide the 2-aryl-substituted pyrrolidine and piperidines 6, 7, 9, and 11 and a series of 2-azabicyclo[3.1.0] derivatives 14-25, including cyclopropane derivatives of proline and of the indolizidine-pyrrolizidine alkaloid ring system. Lithiation-substitutions of N-Boc-N-ethylcyclopropylamine to give 27-29 and lithiation-silylations of N-Boc aziridines to give 31-33 also are reported.

  DOI：

  10.1021/jo00081a002

文献信息

• Asymmetric Syntheses of N-Boc 2-Substituted Pyrrolidines and Piperidines by Intramolecular Cyclization
  作者：Caterina Serino、Nathan Stehle、Yong Sun Park、Saverio Florio、Peter Beak

  DOI：10.1021/jo981553j

  日期：1999.2.1

  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.