(+)-(3R,4S)-3-benzyloxy-4-[(E)-3-(t-butyldiphenylsilyloxy)-1-propenyl]-2-azetidinone | 512171-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (+)-(3R,4S)-3-benzyloxy-4-[(E)-3-(t-butyldiphenylsilyloxy)-1-propenyl]-2-azetidinone
• 英文别名: (3R,4S)-4-[(E)-3-[tert-butyl(diphenyl)silyl]oxyprop-1-enyl]-3-phenylmethoxyazetidin-2-one
• CAS: 512171-64-1
• 化学式: C₂₉H₃₃NO₃Si
• 分子量: 471.671
• InChiKey: HXMNDKMQJKLSQM-XCKXHGCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(3R,4S)-3-benzyloxy-4-[(E)-3-(t-butyldiphenylsilyloxy)-1-propenyl]-2-azetidinone 在 palladium dihydroxide 、 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 、 氢气 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 、 苯 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 99.83h， 生成 (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,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 50.5h， 生成 (+)-(3R,4S)-3-benzyloxy-4-[(E)-3-(t-butyldiphenylsilyloxy)-1-propenyl]-2-azetidinone
  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.