2,2-dichloro-N,N-bis(prop-2-enyl)propanamide | 39089-48-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-dichloro-N,N-bis(prop-2-enyl)propanamide
• CAS: 39089-48-0
• 化学式: C₉H₁₃Cl₂NO
• 分子量: 222.114
• InChiKey: KLWDSTNQLXVMHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  2,2-dichloro-N,N-bis(prop-2-enyl)propanamide 在 五甲基二乙烯三胺 、 sodium carbonate 、 copper(l) chloride 、 维生素 C 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-Chloro-4-(chloromethyl)-3-methyl-1-prop-2-enylpyrrolidin-2-one 、 3-Chloro-4-(chloromethyl)-3-methyl-1-prop-2-enylpyrrolidin-2-one
  参考文献：
  名称：

  A green way to γ-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid

  摘要：

  A 'green' ARGET-ATRC, for the CuCl[PMDETA] catalysed cyclo-isomerization of N-allyl-alpha-polychloroamides to gamma-lactams is described. The process works efficiently (yields 78-96%), uses a bio-solvent, as ethanol, and exploits the reducing feature of ascorbic acid to limit, at a low level (2-4%), the amount of catalyst. To preserve the efficacy of the catalytic cycle, addition of Na2CO3 is essential, which quenches the HCl released during the CuCl[PMDETA] regeneration step. Profitable features of the process are: mild reaction temperatures (25-37 degrees C), relatively short reaction times (usually 5 h) and low solvent volumes (2 mmol of substrate/mL of ethanol). The method, upon stoichiometric adjustment, was also used for the synthesis of alpha,beta-unsaturated-gamma-lactams from N-(2-chloroallyl)-alpha-polychloroamides, via a tandem process involving an ATRC and a reductive [1,2]-elimination. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.025

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。