6S-(4,4-ethylenedioxybutyl)-4R-methyl-2R-(2-oxo-propyl)piperidine | 1436412-08-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 6S-(4,4-ethylenedioxybutyl)-4R-methyl-2R-(2-oxo-propyl)piperidine
• 英文别名: 1-[(2R,4R,6S)-6-[3-(1,3-dioxolan-2-yl)propyl]-4-methylpiperidin-2-yl]propan-2-one
• CAS: 1436412-08-6
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: ZBACJOKYJZWFMY-KWCYVHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6S-(4,4-ethylenedioxybutyl)-4R-methyl-2R-(2-oxo-propyl)piperidine 在 三氟化硼乙醚 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 6.0h， 生成 hippodamine
  参考文献：
  名称：

  Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization

  摘要：

  The first asymmetric total synthesis of (-)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which Is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.

  DOI：

  10.1021/ol4010917
• 作为产物：
  描述：

  6S-(4,4-ethylenedioxybutyl)-4R-methyl-2R-vinyl-piperidine 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 6S-(4,4-ethylenedioxybutyl)-4R-methyl-2R-(2-oxo-propyl)piperidine
  参考文献：
  名称：

  Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization

  摘要：

  The first asymmetric total synthesis of (-)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which Is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.

  DOI：

  10.1021/ol4010917

文献信息

• Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization
  作者：Shintaro Fujita、Taku Sakaguchi、Toyoharu Kobayashi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1021/ol4010917

  日期：2013.6.7

  The first asymmetric total synthesis of (-)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which Is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.