2-<(4-Methylphenyl)imino>-3,3-dimethyl-4-phenyloxethane | 113200-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<(4-Methylphenyl)imino>-3,3-dimethyl-4-phenyloxethane
• 英文别名: Benzenamine, N-(3,3-dimethyl-4-phenyl-2-oxetanylidene)-4-methyl-；3,3-dimethyl-N-(4-methylphenyl)-4-phenyloxetan-2-imine
• CAS: 113200-68-3
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: XZDFDHJXNCSYCH-UHFFFAOYSA-N

物化性质

• 沸点：
  381.7±52.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  苯甲醛 、 dimethylketene-N-p-tolylimine 在 (tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato))ytterbium(III) 作用下， 以 四氯化碳 为溶剂， 反应 36.0h， 以80%的产率得到2-<(4-Methylphenyl)imino>-3,3-dimethyl-4-phenyloxethane
  参考文献：
  名称：

  2-Iminooxetane chemistry. 2. General synthesis from ketene imine-aldehyde cycloadditions

  摘要：

  DOI：

  10.1021/jo00258a019

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）。
• 2-Iminooxetane chemistry. 3. Synthesis of .beta.-hydroxy amides
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00045a024

  日期：1992.9

  Beta-Hydroxy amides were synthesized by hydrolysis of the corresponding 2-iminooxetanes, which were prepared in a very simple step by lanthanide-catalyzed cycloaddition of aldehydes to ketene imines. The stereochemical outcome of the hydrolysis, performed under neutral (DMSO/H2O) or acidic (H2SO4/H2O) conditions, depends on the steric and electronic nature of the substituents, which play a crucial role in the ring-opening mechanism. Experiments done with O-18-labeled water showed that two alternatives are possible: one involving ring opening of the oxetane at the C4-O bond, the other involving ring opening at the C2-O bond.
• 2-Iminooxetane Chemistry. 4. Synthesis of .beta.-Substituted Propionamides
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00083a036

  日期：1994.2

  beta-substituted propionamides (RCHXCR(1)R(2)CONHAr) were synthesized in high yields by addition of protic and aprotic Lewis acids (C6H5SO3H, CF3COOH, CH3COOH, HI, MgBr2, ZnI2, CH3OH, H2O,2,4,6-(NO2)(3)C6H2OH) to 2-iminooxetanes. Studies on the stereochemistry of the acid addition to unsymmetrically C3,C4-monosubstituted 2-iminooxetanes indicate that product distribution depends on the steric and electronic nature of the substitutents of the oxetane moiety as well as on the nucleophilicity of the conjugate base derived from the acid.