(1’R,3S,6S)-1-(2’-hydroxy-1’-phenylethyl)-6-propylpiperidin-3-ol | 1451214-40-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (1’R,3S,6S)-1-(2’-hydroxy-1’-phenylethyl)-6-propylpiperidin-3-ol
• 英文别名: (3S,6S)-1-[(1R)-2-hydroxy-1-phenylethyl]-6-propylpiperidin-3-ol
• CAS: 1451214-40-6
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: JYBGARMYIMCOGR-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1’R,3S,6S)-1-(2’-hydroxy-1’-phenylethyl)-6-propylpiperidin-3-ol 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 15.0h， 以76.8%的产率得到(3S,6S)-6-丙基哌啶-3-醇
  参考文献：
  名称：

  Asymmetric Syntheses of Pyrrolidine and Piperidine Derivatives via Regio- and Stereo-Selective Ring-Opening Reactions of Chiral Aziridine

  摘要：

  Asymmetric synthesis of cyclic beta-amino alcohols (pyrrolidine and piperidine derivatives) has been achieved using a chiral aziridine as the starting material. The key step of this synthetic methodology is regio- and stereo-controlled ring-opening of the chiral aziridine with acetic acid or acetyl chloride.

  DOI：

  10.3987/com-12-s(n)26
• 作为产物：
  描述：

  (1’R,2S)-1-(2’-benzyloxy-1’-phenylethyl)-2-(2-[1,3]dioxolan-2-ylethyl)aziridine 在 碘代三甲硅烷 、 丙基溴化镁 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.33h， 生成 (1’R,3S,6S)-1-(2’-hydroxy-1’-phenylethyl)-6-propylpiperidin-3-ol
  参考文献：
  名称：

  Asymmetric Syntheses of Pyrrolidine and Piperidine Derivatives via Regio- and Stereo-Selective Ring-Opening Reactions of Chiral Aziridine

  摘要：

  Asymmetric synthesis of cyclic beta-amino alcohols (pyrrolidine and piperidine derivatives) has been achieved using a chiral aziridine as the starting material. The key step of this synthetic methodology is regio- and stereo-controlled ring-opening of the chiral aziridine with acetic acid or acetyl chloride.

  DOI：

  10.3987/com-12-s(n)26

文献信息

• Asymmetric Syntheses of Pyrrolidine and Piperidine Derivatives via Regio- and Stereo-Selective Ring-Opening Reactions of Chiral Aziridine
  作者：Kimio Higashiyama、Masataka Matsumura、Emiko Kurita、Takayasu Yamauchi

  DOI：10.3987/com-12-s(n)26

  日期：——

  Asymmetric synthesis of cyclic beta-amino alcohols (pyrrolidine and piperidine derivatives) has been achieved using a chiral aziridine as the starting material. The key step of this synthetic methodology is regio- and stereo-controlled ring-opening of the chiral aziridine with acetic acid or acetyl chloride.