(+)-(8S,8aS)-8-(benzyloxy)-3,5,8,8a-tetrahydro-5-indolizidinone | 512171-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(8S,8aS)-8-(benzyloxy)-3,5,8,8a-tetrahydro-5-indolizidinone
• 英文别名: (8S,8aS)-8-phenylmethoxy-8,8a-dihydro-3H-indolizin-5-one
• CAS: 512171-60-7
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: IIJBZOWAPSBWAX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(8S,8aS)-8-(benzyloxy)-3,5,8,8a-tetrahydro-5-indolizidinone 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以98%的产率得到(8S,8aS)-8-hydroxyhexahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Facile Transformation of 2-Azetidinones to 2-Piperidones:  Application to the Synthesis of the Indolizidine Skeleton and (8S,8aS)-Perhydro-8-indolizinol

  摘要：

  The highly functionalized bicyclic lactam 7 was prepared from diolefinic-2-piperidone 18 by the use of ruthenium-catalyzed RCM, and in turn, 18 was derived via a two-carbon addition process from readily accessible 4-olefinic-2-azetidinone 13. Bicyclic lactams 7 and 20 could serve as potentially valuable intermediates for the chiral synthesis of various hydroxylated indolizidine alkaloids as exemplified by the synthesis of (8S,8aS)-perhydro-8-indolizinol 19.

  DOI：

  10.1021/jo026817n
• 作为产物：
  描述：

  (+)-(3R,4S)-3-benzyloxy-4-[(E)-3-(t-butyldiphenylsilyloxy)-1-propenyl]-2-azetidinone 在 Grubbs catalyst first generation 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 、 苯 为溶剂， 反应 27.83h， 生成 (+)-(8S,8aS)-8-(benzyloxy)-3,5,8,8a-tetrahydro-5-indolizidinone
  参考文献：
  名称：

  Facile Transformation of 2-Azetidinones to 2-Piperidones:  Application to the Synthesis of the Indolizidine Skeleton and (8S,8aS)-Perhydro-8-indolizinol

  摘要：

  The highly functionalized bicyclic lactam 7 was prepared from diolefinic-2-piperidone 18 by the use of ruthenium-catalyzed RCM, and in turn, 18 was derived via a two-carbon addition process from readily accessible 4-olefinic-2-azetidinone 13. Bicyclic lactams 7 and 20 could serve as potentially valuable intermediates for the chiral synthesis of various hydroxylated indolizidine alkaloids as exemplified by the synthesis of (8S,8aS)-perhydro-8-indolizinol 19.

  DOI：

  10.1021/jo026817n

文献信息

• Facile Transformation of 2-Azetidinones to 2-Piperidones:  Application to the Synthesis of the Indolizidine Skeleton and (8<i>S</i>,8a<i>S</i>)-Perhydro-8-indolizinol
  作者：Hyeon Kyu Lee、Jong Soo Chun、Chwang Siek Pak

  DOI：10.1021/jo026817n

  日期：2003.3.1

  The highly functionalized bicyclic lactam 7 was prepared from diolefinic-2-piperidone 18 by the use of ruthenium-catalyzed RCM, and in turn, 18 was derived via a two-carbon addition process from readily accessible 4-olefinic-2-azetidinone 13. Bicyclic lactams 7 and 20 could serve as potentially valuable intermediates for the chiral synthesis of various hydroxylated indolizidine alkaloids as exemplified by the synthesis of (8S,8aS)-perhydro-8-indolizinol 19.