(Z)-N-methyl-4-phenyl-3-butenylamine | 145126-65-4

• 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: (Z)-N-methyl-4-phenyl-3-butenylamine
• 英文别名: (Z)-N-methyl-4-phenylbut-3-en-1-amine
• CAS: 145126-65-4
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: BUYFKEVRYFERNS-UITAMQMPSA-N

物化性质

• 沸点：
  270.4±29.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-N-methyl-4-phenyl-3-butenylamine 在 sodium hydroxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 25.0~350.0 ℃ 、2.67 Pa 条件下， 反应 0.5h， 生成 4-butyl-3-(ethoxycarbonyl)-1-methyl-6-phenyl-1,4-diazabicyclo<4.3.0>nonan-2-one
  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：

  3-[bromo(triphenyl)-lambda5-phosphanyl]-N-methylpropan-1-amine 、 苯甲醛 以53%的产率得到
  参考文献：
  名称：

  Henke Brad R., Kouklis Andrew J., Heathcock Clayton H., J. Org. Chem., 57 (1992) N 26, S 7056-7066

  摘要：

  DOI：

文献信息

• Enantioselective Ring-Closing C–H Amination of Urea Derivatives
  作者：Zijun Zhou、Yuqi Tan、Tatsuya Yamahira、Sergei Ivlev、Xiulan Xie、Radostan Riedel、Marcel Hemming、Masanari Kimura、Eric Meggers

  DOI：10.1016/j.chempr.2020.05.017

  日期：2020.8

  An enantioselective intramolecular C(sp3)–H amination of N-benzoyloxyurea by using a chiral-at-metal ruthenium catalyst is reported, providing chiral 2-imidazolidinones in yields of up to 99% and with up to 99% ee. Catalyst loadings down to 0.05 mol % are feasible. Control experiments support a stepwise nitrene insertion mechanism through hydrogen atom transfer of a ruthenium nitrenoid intermediate

  据报道，通过使用手性金属钌催化剂进行N-苯甲酰氧基脲的对映选择性分子内C（sp 3）-H胺化反应，可提供手性2-咪唑烷酮类，产率高达99％，ee高达99％。降低至0.05mol％的催化剂负载是可行的。对照实验通过钌氮烯类中间体的氢原子转移然后进行自由基重组来支持逐步的氮烯插入机理。手性2-咪唑啉酮在生物活性化合物中普遍存在，并且可以一步转化为手性邻位二胺。证明了该新方法的合成价值用于合成药物左旋咪唑和右旋咪唑，双吲哚生物碱托普汀D和海绵蛋白A的中间体，以及手性有机催化剂。
• Henke Brad R., Kouklis Andrew J., Heathcock Clayton H., J. Org. Chem., 57 (1992) N 26, S 7056-7066
  作者：Henke Brad R., Kouklis Andrew J., Heathcock Clayton H.

  DOI：——

  日期：——
• 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.