(3R,6R)-1-allyl-6-(3,3-dimethoxypropyl)-6-vinylpiperidin-3-ol | 1416404-21-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (3R,6R)-1-allyl-6-(3,3-dimethoxypropyl)-6-vinylpiperidin-3-ol
• 英文别名: (3R,6R)-6-(3,3-dimethoxypropyl)-6-ethenyl-1-prop-2-enylpiperidin-3-ol
• CAS: 1416404-21-1
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: XKOMTSUCBAGNHF-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,6R)-1-allyl-6-(3,3-dimethoxypropyl)-6-vinylpiperidin-3-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 3-[(2S)-2-ethenyl-5-oxo-1-prop-2-enylpiperidin-2-yl]propanal
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b
• 作为产物：
  描述：

  (2R,5R)-1-allyl-5-(benzyloxy)-2-(3,3-dimethoxypropyl)-2-vinylpiperidine 在 lithium naphthalenide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以73%的产率得到(3R,6R)-1-allyl-6-(3,3-dimethoxypropyl)-6-vinylpiperidin-3-ol
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b

文献信息

• Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-<i>epi</i>-FR901483
  作者：Hao-Hua Huo、Xiao-Er Xia、Hong-Kui Zhang、Pei-Qiang Huang

  DOI：10.1021/jo302362b

  日期：2013.1.18

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.