cis-2-<(4-Methoxyphenyl)imino>-3-methyl-4-isopropyloxethane | 142980-43-6

• 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: cis-2-<(4-Methoxyphenyl)imino>-3-methyl-4-isopropyloxethane
• 英文别名: (3R,4S)-N-(4-methoxyphenyl)-3-methyl-4-propan-2-yloxetan-2-imine
• CAS: 142980-43-6；142980-44-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: AMIOEQIQEDNCNA-MFKMUULPSA-N

物化性质

• 沸点：
  324.1±44.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-2-<(4-Methoxyphenyl)imino>-3-methyl-4-isopropyloxethane 在 氢碘酸 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以84%的产率得到(2R,3S)-3-Iodo-2,4-dimethyl-pentanoic acid (4-methoxy-phenyl)-amide
  参考文献：
  名称：

  2-Iminooxetane Chemistry. 4. Synthesis of .beta.-Substituted Propionamides

  摘要：

  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.

  DOI：

  10.1021/jo00083a036

文献信息

• 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.