N-allyl-N-benzyl-2,2-dichloro-2-phenylacetamide | 197857-86-6

• 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-allyl-N-benzyl-2,2-dichloro-2-phenylacetamide
• 英文别名: N-benzyl-2,2-dichloro-2-phenyl-N-prop-2-enylacetamide
• CAS: 197857-86-6
• 化学式: C₁₈H₁₇Cl₂NO
• 分子量: 334.245
• InChiKey: MSBIYAMFRNSCDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-allyl-N-benzyl-2,2-dichloro-2-phenylacetamide 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 以80%的产率得到1-benzyl-3-chloro-4-(chloromethyl)-3-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe0-FeCl3 or CuCl-TMEDA

  摘要：

  The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe-0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00908-3
• 作为产物：
  描述：

  alpha,alpha-二氯苯乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-allyl-N-benzyl-2,2-dichloro-2-phenylacetamide
  参考文献：
  名称：

  Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe0-FeCl3 or CuCl-TMEDA

  摘要：

  The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe-0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00908-3

文献信息

• Efficient and Green Route to γ-Lactams by Copper-Catalysed Reversed Atom Transfer Radical Cyclisation of α-Polychloro-<i>N</i>-allylamides, using a Low Load of Metal (0.5 mol%)
  作者：Franco Bellesia、Andrew J. Clark、Fulvia Felluga、Armando Gennaro、Abdirisak A. Isse、Fabrizio Roncaglia、Franco Ghelfi

  DOI：10.1002/adsc.201300132

  日期：2013.5.17

  The cyclisation of N‐allyl‐N‐substituted‐α‐polychloroamides is efficiently obtained through a copper‐catalysed activators regenerated by electron transfer–atom transfer radical cyclisation process, with a metal load of only 0.5 mol%. The redox catalyst is introduced in its inactive form as copper(II) chloride/[nitrogen ligand] complex, and continuously regenerated to the active copper(I) chloride/[nitrogen

  通过电子转移-原子转移自由基环化过程再生的铜催化活化剂，可以有效地实现N-烯丙基-N-取代-α-聚氯酰胺的环化，金属负载量仅为0.5 mol％。氧化还原催化剂以其惰性形式作为氯化铜（II）/ [氮配体]配合物引入，并通过抗坏血酸连续再生为活性氯化铜（I）/ [氮配体]物种。为了保持催化剂的完整性，在每个再生循环后释放的盐酸已被碳酸盐淬灭。溶剂的选择至关重要，在乙酸乙酯-乙醇（3：1）中观察到最佳性能。
• Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe0-FeCl3 or CuCl-TMEDA
  作者：Miriam Benedetti、Luca Forti、Franco Ghelfi、Ugo Maria Pagnoni、Roberto Ronzoni

  DOI：10.1016/s0040-4020(97)00908-3

  日期：1997.10

  The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe-0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively. (C) 1997 Elsevier Science Ltd.