(4S,4'R)-1-(4-methoxyphenyl)-3-[4-(phenylmethoxy)phenylmethylidene]-4-(1,4-dioxaspiro[4.5]dec-2-yl)azetidin-2-one | 441786-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,4'R)-1-(4-methoxyphenyl)-3-[4-(phenylmethoxy)phenylmethylidene]-4-(1,4-dioxaspiro[4.5]dec-2-yl)azetidin-2-one
• CAS: 441786-64-7
• 化学式: C₃₂H₃₃NO₅
• 分子量: 511.618
• InChiKey: ZZHZGXBEUVMYRC-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,4'R)-1-(4-methoxyphenyl)-3-[4-(phenylmethoxy)phenylmethylidene]-4-(1,4-dioxaspiro[4.5]dec-2-yl)azetidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以98%的产率得到(3S,4S,4'R)-1-(4-methoxyphenyl)-3-(4-hydroxyphenylmethyl)-4-(1,4-dioxaspiro[4.5]dec-2-yl)azetidin-2-one
  参考文献：
  名称：

  Efficient and highly stereoselective synthesis of a β-Lactam inhibitor of the serine protease prostate-specific antigen

  摘要：

  An efficient synthesis of a beta-lactam precursor of the serine protease, prostate-specific antigen inhibitor 1 has been accomplished. The synthesis relies on two completely stercoselective reactions that allow the introduction of the stereocenters at C-3 and C-4 of the azetidinone ring in a predictable manner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00017-2
• 作为产物：
  描述：

  (3S,4R,4'R)-1-(4-methoxyphenyl)-3-hydroxy-4-(1,4-dioxaspiro[4.5]dec-2-yl)azetidin-2-one 在 正丁基锂 、 phosphorus pentoxide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 22.67h， 生成 (4S,4'R)-1-(4-methoxyphenyl)-3-[4-(phenylmethoxy)phenylmethylidene]-4-(1,4-dioxaspiro[4.5]dec-2-yl)azetidin-2-one
  参考文献：
  名称：

  Efficient and highly stereoselective synthesis of a β-Lactam inhibitor of the serine protease prostate-specific antigen

  摘要：

  An efficient synthesis of a beta-lactam precursor of the serine protease, prostate-specific antigen inhibitor 1 has been accomplished. The synthesis relies on two completely stercoselective reactions that allow the introduction of the stereocenters at C-3 and C-4 of the azetidinone ring in a predictable manner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00017-2