N-methyl-N-(2-phenyl-2-cyclohex-1-yl)trichloroacetamide | 256506-05-5

• 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-methyl-N-(2-phenyl-2-cyclohex-1-yl)trichloroacetamide
• 英文别名: 2,2,2-trichloro-N-methyl-N-(2-phenylcyclohex-2-en-1-yl)acetamide
• CAS: 256506-05-5
• 化学式: C₁₅H₁₆Cl₃NO
• 分子量: 332.657
• InChiKey: AAIOFOZJQIPPGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(2-phenyl-2-cyclohex-1-yl)trichloroacetamide 在 copper(l) chloride 三正丁基氢锡 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 cis-octahydro-1-methyl-3a-phenylindol-2-one
  参考文献：
  名称：

  通过铜或钌催化的N-烯丙基三氯乙酰胺的环化立体选择性地制备双环内酰胺：吡咯烷生物碱骨架的新进入

  摘要：

  某些N-烯丙基三氯乙酰胺的环化为几种双环内酰胺提供了立体选择方法。

  DOI：

  10.1039/c39850000518
• 作为产物：
  描述：

  N-methyl-N-(2-phenyl-2-cyclohexen-1-yl)amine 、 三氯乙酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以1.09 g的产率得到N-methyl-N-(2-phenyl-2-cyclohex-1-yl)trichloroacetamide
  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

文献信息

• Stereoselective preparation of bicyclic lactams by copper- or ruthenium-catalysed cyclization of N-allyltrichloroacetamides: a novel entry to pyrrolidine alkaloid skeletons
  作者：Hideo Nagashima、Ken-ichi Ara、Hidetoshi Wakamatsu、Kenji Itoh

  DOI：10.1039/c39850000518

  日期：——

  Cyclization of certain N-allyltrichloroacetamides provides a stereoselective method for several bicyclic lactams.

  某些N-烯丙基三氯乙酰胺的环化为几种双环内酰胺提供了立体选择方法。
• Synthetic Studies of <i>cis</i>-3a-Aryloctahydroindole Derivatives by Copper-Catalyzed Cyclization of <i>N</i>-Allyltrichloroacetamides:  Facile Construction of Benzylic Quaternary Carbons by Carbon−Carbon Bond-Forming Reactions
  作者：Sho-ichi Iwamatsu、Kouki Matsubara、Hideo Nagashima

  DOI：10.1021/jo9912146

  日期：1999.12.1

  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.