3-methyl-N-(4-methylphenyl)but-2-en-1-imine oxide | 817195-51-0

• 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: 3-methyl-N-(4-methylphenyl)but-2-en-1-imine oxide
• CAS: 817195-51-0；1025058-75-6
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: KTGJRSFAOPNSHB-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-N-(4-methylphenyl)but-2-en-1-imine oxide 、 dimethyl (E)-2-styrylcyclopropane-1,1-dicarboxylate 在 magnesium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (3S,6R)-3-(2-Methyl-propenyl)-6-((E)-styryl)-2-p-tolyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester 、 (3S,6S)-3-(2-Methyl-propenyl)-6-((E)-styryl)-2-p-tolyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Magnesium Iodide Promoted Reactions of Nitrones with Cyclopropanes:  A Synthesis of Tetrahydro-1,2-oxazines

  摘要：

  Anhydrous magnesium iodide (MgI2) is shown to be an effective promoter of the "homo 3+2" dipolar cycloaddition of nitrones with 1,1-cyclopropane diesters. In almost all cases the products tetrahydro-1,2-oxazines are formed in excellent yields. The reactions are highly diastereoselective for a cis relationship between the substitutents at the 3- and 6-positions on the tetrahydrooxazine ring. As an alternative to using a preformed nitrone, the reaction may be performed in a 3-component sense by combining an aldehyde, an hydroxylamine, and the cyclopropane in the presence of catalytic MgI2.

  DOI：

  10.1021/jo048768f
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 4-硝基甲苯 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以50%的产率得到3-methyl-N-(4-methylphenyl)but-2-en-1-imine oxide
  参考文献：
  名称：

  Magnesium Iodide Promoted Reactions of Nitrones with Cyclopropanes:  A Synthesis of Tetrahydro-1,2-oxazines

  摘要：

  Anhydrous magnesium iodide (MgI2) is shown to be an effective promoter of the "homo 3+2" dipolar cycloaddition of nitrones with 1,1-cyclopropane diesters. In almost all cases the products tetrahydro-1,2-oxazines are formed in excellent yields. The reactions are highly diastereoselective for a cis relationship between the substitutents at the 3- and 6-positions on the tetrahydrooxazine ring. As an alternative to using a preformed nitrone, the reaction may be performed in a 3-component sense by combining an aldehyde, an hydroxylamine, and the cyclopropane in the presence of catalytic MgI2.

  DOI：

  10.1021/jo048768f

文献信息

• Magnesium Iodide Promoted Reactions of Nitrones with Cyclopropanes:  A Synthesis of Tetrahydro-1,2-oxazines
  作者：Michael D. Ganton、Michael A. Kerr

  DOI：10.1021/jo048768f

  日期：2004.11.1

  Anhydrous magnesium iodide (MgI2) is shown to be an effective promoter of the "homo 3+2" dipolar cycloaddition of nitrones with 1,1-cyclopropane diesters. In almost all cases the products tetrahydro-1,2-oxazines are formed in excellent yields. The reactions are highly diastereoselective for a cis relationship between the substitutents at the 3- and 6-positions on the tetrahydrooxazine ring. As an alternative to using a preformed nitrone, the reaction may be performed in a 3-component sense by combining an aldehyde, an hydroxylamine, and the cyclopropane in the presence of catalytic MgI2.