cis-3-Phenoxy-4-phenyl-1-(1'-propenyl)-2-azetidinone | 118673-19-1

• 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: cis-3-Phenoxy-4-phenyl-1-(1'-propenyl)-2-azetidinone
• CAS: 118673-19-1；118758-72-8
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: IMHYEVFVVYYTGJ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-3-Phenoxy-4-phenyl-1-(1'-propenyl)-2-azetidinone 在 potassium permanganate 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 3-phenoxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  Stereocontrolled synthesis of N-vinyl-, N-(1'-propenyl)-, and N-unsubstituted-.beta.-lactams from 2-aza-1,3-butadienes via the Staudinger reaction

  摘要：

  2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale. Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-beta-lactams. Excellent cis-stereoselectivity was observed in the reaction of 2-aza-1,3-butadienes 2 and 5 with Bose-Evans ketenes and Sheehan ketenes, whereas reaction with a Moore ketene gave, as expected, a trans beta-lactam. N-Formyl, N-vinyl, and N-(1'-propenyl) groups at the beta-lactam nitrogen could be cleaved oxidatively in one step and in good yields by treatment with potassium permanganate. It was also found that the N-vinyl group can be removed successfully under hydrolytic, conditions to yield N-unsubstituted-beta-lactams.

  DOI：

  10.1021/jo00073a042
• 作为产物：
  描述：

  (1E,3E/Z)-2-Aza-1-phenyl-1,3-pentadiene 、 苯氧乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以66%的产率得到cis-3-Phenoxy-4-phenyl-1-(1'-propenyl)-2-azetidinone
  参考文献：
  名称：

  Stereocontrolled synthesis of N-vinyl-, N-(1'-propenyl)-, and N-unsubstituted-.beta.-lactams from 2-aza-1,3-butadienes via the Staudinger reaction

  摘要：

  2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale. Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-beta-lactams. Excellent cis-stereoselectivity was observed in the reaction of 2-aza-1,3-butadienes 2 and 5 with Bose-Evans ketenes and Sheehan ketenes, whereas reaction with a Moore ketene gave, as expected, a trans beta-lactam. N-Formyl, N-vinyl, and N-(1'-propenyl) groups at the beta-lactam nitrogen could be cleaved oxidatively in one step and in good yields by treatment with potassium permanganate. It was also found that the N-vinyl group can be removed successfully under hydrolytic, conditions to yield N-unsubstituted-beta-lactams.

  DOI：

  10.1021/jo00073a042

文献信息

• 2-aza-1,3-dienes as novel precursors for the synthesis of -unsubstituted β-lactams. A three step synthesis of 4-acetoxy-3-phenoxy-2-azeridinone
  作者：Gunda I Georg、Joydeep Kant、Ping He、Ana Maria Ly、Lynn Lampe

  DOI：10.1016/s0040-4039(00)87894-6

  日期：1988.1