2-Phenyl-3-(hydroxymethyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-Phenyl-3-(hydroxymethyl)piperidine
• 英文别名: Tert-butyl 3-(hydroxymethyl)-2-phenylpiperidine-1-carboxylate
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: VDBHRFYQZSNDQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl benzyl(pent-4-en-1-yl)carbamate 在 四甲基乙二胺 、 仲丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 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

文献信息

• 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
  作者：Peter Beak、Shengde Wu、Eul Kyun Yum、Young Moo Jun

  DOI：10.1021/jo00081a002

  日期：1994.1

  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.