(5R,6S)-1-allyl-5-(benzyloxy)-6-(4-methoxybenzyl)piperidin-2-one | 1416404-16-4

• 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: (5R,6S)-1-allyl-5-(benzyloxy)-6-(4-methoxybenzyl)piperidin-2-one
• 英文别名: (5R,6S)-6-[(4-methoxyphenyl)methyl]-5-phenylmethoxy-1-prop-2-enylpiperidin-2-one
• CAS: 1416404-16-4
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: KQISXVBXRWJWKF-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S)-1-allyl-5-(benzyloxy)-6-(4-methoxybenzyl)piperidin-2-one 、 3-(tert-butyldimethylsilyloxy)-1-propyllithium 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 6.0h， 以35%的产率得到(5R,6S)-1-allyl-5-(benzyloxy)-2,2-bis[3-(tert-butyldimethylsilyloxy)propyl]-6-(4-methoxybenzyl)piperidine
  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：

  (R)-1-allyl-3-benzyloxy-2,6-piperidinedione 、 4-methoxybenzylmagnesium chloride 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 以7.3 g的产率得到(5R,6S)-1-allyl-5-(benzyloxy)-6-(4-methoxybenzyl)piperidin-2-one
  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.