1-((1'S,2'S)-1'-phenyl-1'-hydroxy-3'-acetoxy-2'-propyl)-3(R)-phthalimido-4(S)-styryl-azetidin-2-one | 191418-21-0

• 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: 1-((1'S,2'S)-1'-phenyl-1'-hydroxy-3'-acetoxy-2'-propyl)-3(R)-phthalimido-4(S)-styryl-azetidin-2-one
• CAS: 191418-21-0
• 化学式: C₃₀H₂₆N₂O₆
• 分子量: 510.546
• InChiKey: UPAPAOACUZQLLJ-HKPUHCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-((1'S,2'S)-1'-phenyl-1'-hydroxy-3'-acetoxy-2'-propyl)-3(R)-phthalimido-4(S)-styryl-azetidin-2-one 在 chromium(VI) oxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 1-(3'-phenyl-propen-3'-on-2'-yl)-3(R)-phthalimido-4(S)-styryl-azetidin-2-one
  参考文献：
  名称：

  2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones

  摘要：

  3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-alpha/beta-ratio could be influenced by: the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00483-3
• 作为产物：
  描述：

  (1S,2S)-(+)-2-氨基-1-苯基-1,3-丙二醇 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 75.0h， 生成 1-((1'S,2'S)-1'-phenyl-1'-hydroxy-3'-acetoxy-2'-propyl)-3(R)-phthalimido-4(S)-styryl-azetidin-2-one
  参考文献：
  名称：

  2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones

  摘要：

  3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-alpha/beta-ratio could be influenced by: the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00483-3