(1S,3S,5S,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]nonan-4-one | 1416404-28-8

• 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: (1S,3S,5S,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]nonan-4-one
• 英文别名: (1S,3S,5S,6R)-1-ethenyl-3-[(4-methoxyphenyl)methyl]-6-phenylmethoxy-2-prop-2-enyl-2-azabicyclo[3.3.1]nonan-4-one
• CAS: 1416404-28-8
• 化学式: C₂₈H₃₃NO₃
• 分子量: 431.575
• InChiKey: CNSNEHMQPKWIEM-NAVOWQOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3S,5S,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]nonan-4-one 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以94%的产率得到(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene
  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：

  (1S,5S,6R)-2-allyl-1-vinyl-2-azaspiro[bicyclo[3.3.1]nonane-4,2'-[1,3]dioxolan]-6-ol 在 盐酸 、 四甲基乙二胺 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 42.5h， 生成 (1S,3S,5S,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]nonan-4-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.