N-methyl-N-(2-phenyl-2-cyclohexen-1-yl)amine | 65078-73-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-(2-phenyl-2-cyclohexen-1-yl)amine
• 英文别名: 2-Phenyl-3-methylamino-cyclohexen；3-Methylamino-2-phenyl-cyclohexen；methyl-(2-phenyl-cyclohex-2-enyl)-amine；N-methyl-2-phenylcyclohex-2-en-1-amine
• CAS: 65078-73-1
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: CAHMZLOIMYILDK-UHFFFAOYSA-N

物化性质

• 沸点：
  292.5±40.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(2-phenyl-2-cyclohexen-1-yl)amine 在 2,2'-联吡啶 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3,3,4-trichloro-1-methyl-3a-phenyl-2,3,3a,4,5,6,7,7a-octahydroindol-2-one
  参考文献：
  名称：

  Synthetic Studies of cis-3a-Aryloctahydroindole Derivatives by Copper-Catalyzed Cyclization of N-Allyltrichloroacetamides:  Facile Construction of Benzylic Quaternary Carbons by Carbon−Carbon Bond-Forming Reactions

  摘要：

  Cyclization of N-(2-aryl-2-cyclohexen-1-yl)trichloroacetamides by a copper catalyst was investigated. It is crucially important for successful cyclization under mild conditions that alkoxycarbonyl groups are introduced to the nitrogen atom of the N-allyltrichloroacetamides as well as that CuCl(bipyridine) is used as the catalyst. Three compounds, N-(2-phenyl-2-cyclohexen-1-yl)-, N-[2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-yl]-, and N-[2-(3,4-methylenedioxyphenyl)-2-cyclohexen-1-yl]-trichloroacetamides, where the Cbz or MeO2C- group was attached to the nitrogen atom, were instantly converted to the corresponding trichlorinated cis-3a-aryloctahydroindol-2-ones in high yields at room temperature. The reactions offer a facile access to alkaloid skeletons such as mesembrines and crinines; as the simplest examples, total synthesis of (+/-)-mesembrane and (+/-)-crinane was accomplished. The effect of alkoxycarbonyl substituents in the amide group was compared with that of the methyl substituent. N-Methyl-N-(2-phenyl-2-cyclohexen-1-yl)trichloro- acetamide quickly reacted in the presence of CuCl(bipyridine) catalyst; however, the products were a mixture of complicated materials including a small amount of the desired lactam. The role of the alkoxycarbonyl group was discussed in terms of rate of rotation of the N-C bond in the N-allyltrichloroacetamides; variable-temperature NMR studies and X-ray structure determination of related compounds were carried out as supporting evidence.

  DOI：

  10.1021/jo9912146
• 作为产物：
  描述：

  在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 以11.2 mg的产率得到N-methyl-N-(2-phenyl-2-cyclohexen-1-yl)amine
  参考文献：
  名称：

  双吖啶/钴催化可见光辅助合成烯丙基三甲酰胺

  摘要：

  通过双可见光光氧化还原/钴肟催化描述了苯乙烯基碳-碳双键与三氟甲酰胺的脱氢功能化。在化学计量的无受体条件下，以中等至良好的产率（高达 88%）分离了一系列烯丙基三甲酰胺（20 个实例）。专用标记以及光谱实验能够揭示串联的光催化和化学催化循环。

  DOI：

  10.1002/adsc.202101329

文献信息

• Berti,G. et al., Gazzetta Chimica Italiana, 1977, vol. 107, p. 175 - 180
  作者：Berti,G. et al.

  DOI：——

  日期：——