1-[(1'S,5'S,6'R)-1'-ethenyl-6'-phenylmethoxyspiro[1,3-dioxolane-2,4'-2-azabicyclo[3.3.1]nonane]-2'-yl]prop-2-en-1-one | 1395688-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 1-[(1'S,5'S,6'R)-1'-ethenyl-6'-phenylmethoxyspiro[1,3-dioxolane-2,4'-2-azabicyclo[3.3.1]nonane]-2'-yl]prop-2-en-1-one
• CAS: 1395688-01-3
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: NIUOVVGNADCPRE-ZVDOUQERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(1'S,5'S,6'R)-1'-ethenyl-6'-phenylmethoxyspiro[1,3-dioxolane-2,4'-2-azabicyclo[3.3.1]nonane]-2'-yl]prop-2-en-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 titanium(IV) isopropylate 、 盐酸 、 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 samarium diiodide 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三(4-氯苯基)膦 、 DIAD 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， -78.0~85.0 ℃ 、101.33 kPa 条件下， 反应 50.08h， 生成 Phosphoric acid dibenzyl ester (1S,3S,6S,7S,8R,9S)-7-hydroxy-6-(4-methoxy-benzyl)-3-methylamino-5-aza-tricyclo[6.3.1.01,5]dodec-9-yl ester
  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 四(三苯基膦)钯 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 1-[(1'S,5'S,6'R)-1'-ethenyl-6'-phenylmethoxyspiro[1,3-dioxolane-2,4'-2-azabicyclo[3.3.1]nonane]-2'-yl]prop-2-en-1-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.