4-Phenyl-3,3-dimethyl-1-p-tolylazetidin-2-one | 74185-91-4

• 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: 4-Phenyl-3,3-dimethyl-1-p-tolylazetidin-2-one
• 英文别名: 3,3-Dimethyl-1-(4-methylphenyl)-4-phenyl-2-azetidinone；3,3-dimethyl-1-(4-methylphenyl)-4-phenylazetidin-2-one
• CAS: 74185-91-4
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: MSOAHGPRVJWXHK-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  465.4±44.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-<(4-Methylphenyl)imino>-3,3-dimethyl-4-phenyloxethane 在 Yb(HFC)3 作用下， 反应 0.5h， 以78%的产率得到4-Phenyl-3,3-dimethyl-1-p-tolylazetidin-2-one
  参考文献：
  名称：

  Lanthanide- and DMSO-Induced Ring Opening of 2-Iminooxetanes: Synthesis of .beta.-Lactams and .beta.-Keto Amides

  摘要：

  2-Iminooxetanes (1), generated by lanthanide-catalyzed heterocycloaddition of aldehydes to ketene imines, are versatile synthons for beta-lactams (2) and for beta-keto amides (3). Conversion of 1 into 2 and 3 can be accomplished by either lanthanide-induced or oxidative (DMSO) ring opening, respectively.

  DOI：

  10.1021/jo00109a038

文献信息

• 2-iminoxetanes from ketenimine-aldehyde cycloadditions. Part 1: Synthesis and controlled ring opening of 2-N-p-tolylimino-3,3-dimethyl-4-phenyloxetane
  作者：Gaetano Barbaro、Arturo Battaglia*、Patrizia Giorgianni

  DOI：10.1016/s0040-4039(00)96266-x

  日期：——

  Regiospecific cycloaddition of benzaldehyde to dimethylketene-N-p-tolylimine, catalyzed by lanthanide shift reagents, afforded the corresponding 2-iminoxetane. Controlled ring opening showed the oxetane to be a versatile building block for the synthesis of the corresponding acyclic -a- minoalcohol, β-keto and β-hydroxyamide. In addition isomerization produced the corresponding 2-azetidinone (β-lactam).

  在镧系元素移位试剂的催化下，苯甲醛与苯二酚的区域特异性环加成反应得到相应的2-亚氨基氧杂环丁烷。受控的开环表明氧杂环丁烷是合成相应的无环-α-氨基醇，β-酮和β-羟酰胺的通用结构单元。另外，异构化产生了相应的2-氮杂环丁酮（β-内酰胺）。
• Preparation of .beta.-lactams by the condensation of lithium ester enolates with aryl aldimines
  作者：Charles Gluchowski、Lynn Cooper、David E. Bergbreiter、Martin Newcomb

  DOI：10.1021/jo01305a008

  日期：1980.8
• GLUCHOWSKI C.; COOPER L.; BERGBREITER D. E.; NEWCOMB M., J. ORG. CHEM., 1980, 45, NO 17, 3413-3416
  作者：GLUCHOWSKI C.、 COOPER L.、 BERGBREITER D. E.、 NEWCOMB M.

  DOI：——

  日期：——
• Lanthanide- and DMSO-Induced Ring Opening of 2-Iminooxetanes: Synthesis of .beta.-Lactams and .beta.-Keto Amides
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00109a038

  日期：1995.2

  2-Iminooxetanes (1), generated by lanthanide-catalyzed heterocycloaddition of aldehydes to ketene imines, are versatile synthons for beta-lactams (2) and for beta-keto amides (3). Conversion of 1 into 2 and 3 can be accomplished by either lanthanide-induced or oxidative (DMSO) ring opening, respectively.