(3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one | 1333388-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one
• 英文别名: (3S,8R,8aS)-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-8-phenylmethoxy-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 1333388-41-2
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: KZGYRBSTXNCZGB-FUJDEKNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 以90%的产率得到(3S,8R,8aS)-8-hydroxy-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Concise Asymmetric Total Synthesis of 9-epi-Sessilifoliamide J

  摘要：

  A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI2-mediated coupling lactoniation. The absolute configuration of the natural sessilifoliamide J was established.

  DOI：

  10.1021/ol202140y
• 作为产物：
  描述：

  (8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以60%的产率得到(3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Concise Asymmetric Total Synthesis of 9-epi-Sessilifoliamide J

  摘要：

  A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI2-mediated coupling lactoniation. The absolute configuration of the natural sessilifoliamide J was established.

  DOI：

  10.1021/ol202140y

文献信息

• Concise Asymmetric Total Synthesis of 9-<i>epi</i>-Sessilifoliamide J
  作者：Shi-Chuan Tuo、Jian-Liang Ye、Ai-E Wang、Su-Yu Huang、Pei-Qiang Huang

  DOI：10.1021/ol202140y

  日期：2011.10.7

  A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI2-mediated coupling lactoniation. The absolute configuration of the natural sessilifoliamide J was established.