N-benzylhex-5-en-1-imine | 176171-61-2

• 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: N-benzylhex-5-en-1-imine
• CAS: 176171-61-2
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: FXWDWFCLFKMQBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzylhex-5-en-1-imine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 N-benzylhex-5-en-1-amine
  参考文献：
  名称：

  Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles

  摘要：

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.

  DOI：

  10.1021/jo00052a015
• 作为产物：
  描述：

  5-己烯-1-醇 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 N-benzylhex-5-en-1-imine
  参考文献：
  名称：

  Ugi Four-Component Reaction of Alcohols: Stoichiometric and Catalytic Oxidation/MCR Sequences

  摘要：

  A new, simple, and efficient procedure for the one-pot Ugi four-component reaction of alcohols instead of aldehydes is described. Using a stoichiometric amount of IBX or only 1-2% of sodium 2-iodobenzenesulfonate in the presence of Oxone, a wide range of primary alcohols were oxidized to the aldehyde that were directly engaged in the Ugi four-component reaction to afford alpha-acetamidoamides in good to excellent yields.

  DOI：

  10.1021/ol401181a

文献信息

• A Diversity-Oriented Synthesis ofα-Amino Acid Derivatives by a Silyltelluride-Mediated Radical Coupling Reaction of Imines and Isonitriles
  作者：Shigeru Yamago、Hiroshi Miyazoe、Takeyoshi Nakayama、Masaki Miyoshi、Junichi Yoshida

  DOI：10.1002/anie.200390039

  日期：2003.1.3
• Ugi Four-Component Reaction of Alcohols: Stoichiometric and Catalytic Oxidation/MCR Sequences
  作者：Fleur Drouet、Géraldine Masson、Jieping Zhu

  DOI：10.1021/ol401181a

  日期：2013.6.7

  A new, simple, and efficient procedure for the one-pot Ugi four-component reaction of alcohols instead of aldehydes is described. Using a stoichiometric amount of IBX or only 1-2% of sodium 2-iodobenzenesulfonate in the presence of Oxone, a wide range of primary alcohols were oxidized to the aldehyde that were directly engaged in the Ugi four-component reaction to afford alpha-acetamidoamides in good to excellent yields.
• Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles
  作者：Brad R. Henke、Andrew J. Kouklis、Clayton H. Heathcock

  DOI：10.1021/jo00052a015

  日期：1992.12

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.