(+)-(3R,4S)-4-methyl-3-(benzyloxy)-2-azetidinone | 614733-18-5

• 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)-4-methyl-3-(benzyloxy)-2-azetidinone
• 英文别名: (3R,4S)-4-methyl-3-phenylmethoxyazetidin-2-one
• CAS: 614733-18-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: YCVBMZYNOKGAFE-WCBMZHEXSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  365.9±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(3R,4S)-4-methyl-3-(benzyloxy)-2-azetidinone 在 palladium on activated charcoal 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 、 四丁基碘化铵 、 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 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 24.34h， 生成 (-)-(5S,6S)-1-benzyl-5-(benzyloxy)6-methyl-hexahydro-2-pyridinone
  参考文献：
  名称：

  Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids

  摘要：

  Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having pre-installed substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-alpha,beta-unsaturated ester and lactam formation. For the synthetic application to the naturally occurring piperidine alkaloids, such as Prosopis and Cassia alkaloids, 5-hydroxy-2-piperidones (+)-13 and (-)-24 were prepared from 2-azetidinones (-)-6b and (+)-18 via two-carbon ring homologation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01063-9
• 作为产物：
  描述：

  (+)-(3R,4S)-1-(4-methoxyphenyl)-3-benzyloxy-4-hydroxymethyl-2-azetidinone 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 氢气 、 碳酸氢钠 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 70.0 ℃ 、344.74 kPa 条件下， 反应 14.5h， 生成 (+)-(3R,4S)-4-methyl-3-(benzyloxy)-2-azetidinone
  参考文献：
  名称：

  Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids

  摘要：

  Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having pre-installed substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-alpha,beta-unsaturated ester and lactam formation. For the synthetic application to the naturally occurring piperidine alkaloids, such as Prosopis and Cassia alkaloids, 5-hydroxy-2-piperidones (+)-13 and (-)-24 were prepared from 2-azetidinones (-)-6b and (+)-18 via two-carbon ring homologation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01063-9

文献信息

• Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids
  作者：Hyeon Kyu Lee、Jong Soo Chun、Chwang Siek Pak

  DOI：10.1016/s0040-4020(03)01063-9

  日期：2003.8

  Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having pre-installed substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-alpha,beta-unsaturated ester and lactam formation. For the synthetic application to the naturally occurring piperidine alkaloids, such as Prosopis and Cassia alkaloids, 5-hydroxy-2-piperidones (+)-13 and (-)-24 were prepared from 2-azetidinones (-)-6b and (+)-18 via two-carbon ring homologation. (C) 2003 Elsevier Ltd. All rights reserved.