N-Benzyl-2,2,2-trichloro-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide | 730961-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Benzyl-2,2,2-trichloro-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide
• 英文别名: N-benzyl-2,2,2-trichloro-N-[(4-oxocyclohex-2-en-1-yl)methyl]acetamide
• CAS: 730961-16-7
• 化学式: C₁₆H₁₆Cl₃NO₂
• 分子量: 360.668
• InChiKey: DFSOUEWMKADQIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzyl-2,2,2-trichloro-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以70%的产率得到(4aR,8aR)-2-Benzyl-hexahydro-isoquinoline-3,6-dione
  参考文献：
  名称：

  Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis -perhydroisoquinoline-3,6-diones

  摘要：

  Intramolecular reactions between 1-(carbamoyl)dichloromethyl radicals and enones acting as radical acceptors are reported for the first time. The Bu3SnH promoted 6-exo reaction of trichloroacetamides with enones, avoiding the 1,5-hydrogen transfer, constitutes a new synthetic entry to cis-perhydoisoquinoline-3,6-diones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.104
• 作为产物：
  描述：

  N-benzyl-2,2,2-trichloro-N-[(4-oxocyclohexyl)methyl]acetamide 在 2-碘酰基苯甲酸 作用下， 以80%的产率得到N-Benzyl-2,2,2-trichloro-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide
  参考文献：
  名称：

  Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis -perhydroisoquinoline-3,6-diones

  摘要：

  Intramolecular reactions between 1-(carbamoyl)dichloromethyl radicals and enones acting as radical acceptors are reported for the first time. The Bu3SnH promoted 6-exo reaction of trichloroacetamides with enones, avoiding the 1,5-hydrogen transfer, constitutes a new synthetic entry to cis-perhydoisoquinoline-3,6-diones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.104

文献信息

• Catalyst-free photo-induced aerobic radical synthesis of lactams from <i>N</i>-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light
  作者：Faïza Diaba、Gisela Trenchs

  DOI：10.1039/d3ob01804k

  日期：——

  The first violet light-mediated synthesis of γ- and δ-lactams from N-alkenyl trichloroacetamides is reported in tetrahydrofuran or 2-methyltetrahydrofuran alone. These catalyst and additive-free reactions are achieved with non-anhydrous solvents and under an air atmosphere where the solvent serves as the radical initiator.

  据报道，仅在四氢呋喃或 2-甲基四氢呋喃中，首次通过紫光介导从N-烯基三氯乙酰胺合成 γ-和 δ-内酰胺。这些无催化剂和无添加剂的反应是使用非无水溶剂在空气气氛下实现的，其中溶剂充当自由基引发剂。