cis-2-<(4-methoxyphenyl)imino>-3-methyl-4-n-propyloxyetane | 116748-89-1

• 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-n-propyloxyetane
• 英文别名: cis-2-<(4-Methoxyphenyl)imino>-3-methyl-4-propyloxethane；cis-2-[(4-methoxyphenyl)imino]-3-methyl-4-n-propyloxyetane；(3R,4S)-N-(4-methoxyphenyl)-3-methyl-4-propyloxetan-2-imine
• CAS: 116748-89-1
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: DCHWWDPTWYNJTK-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 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-n-propyloxyetane 在 potassium tert-butylate 、 氢碘酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 1-(4-methoxyphenyl)-3-methyl-4-(1-propyl)azetidin-2-one
  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
• 作为产物：
  描述：

  正丁醛 、 Methylketene N-p-methoxyphenylimine 在 Yb(hfc)3(+) 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以50%的产率得到trans-2-<(4-methoxyphenyl)imino>-3-methyl-4-n-propyloxyetane
  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

• 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.
• 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. 2. General synthesis from ketene imine-aldehyde cycloadditions
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00258a019

  日期：1988.11
• 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.