N-benzyl-2,2-dichloro-N-cyclohex-2-en-1-ylbutanamide | 1215092-43-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-benzyl-2,2-dichloro-N-cyclohex-2-en-1-ylbutanamide
• CAS: 1215092-43-5
• 化学式: C₁₇H₂₁Cl₂NO
• 分子量: 326.266
• InChiKey: HWDUBMIUHNZFEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-benzyl-2,2-dichloro-N-cyclohex-2-en-1-ylbutanamide 在 三[2-(二甲氨基)乙基]胺 、 sodium carbonate 、 copper dichloride 、 维生素 C 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 8.0h， 以96%的产率得到
  参考文献：
  名称：

  铜催化的α-多氯-N-烯丙酰胺的反向原子转移自由基环化反应的高效和绿色路线，使用低负荷的金属（0.5摩尔％）

  摘要：

  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。

  DOI：

  10.1002/adsc.201300132
• 作为产物：
  描述：

  2,2-dichlorobutanoyl chloride 、 N-benzyl-N-(2-cyclohexenyl)amine 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以98%的产率得到N-benzyl-2,2-dichloro-N-cyclohex-2-en-1-ylbutanamide
  参考文献：
  名称：

  Functional rearrangement of 3-Cl or 3,3-diCl-γ-lactams bearing a secondary 1-chloroalkyl substituent at C-4

  摘要：

  The study of the reaction with MeONa/MeOH of chlorinated gamma-lactams. prepared from the atom transfer radical cyclization of N-allyl-alpha-perchloroamides, has been extended to the case of substiates carrying an exo halogen atom on a branched carbon Only with secondary exo C-Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, Which With trichloro-lactams can proceed further to give 4-alkylidene derivatives From a practical point of view, the outcome of the reaction with di- or trichloio N-cinnamylamides is synthetically valuable, affording the 5-methoxy-IH-pyrrol-2(5H)-one or 3-benzylidenepyrrlidine-2.5-dione. respectively. in good to excellent yield (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.11.111

文献信息

• A green way to γ-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid
  作者：Roberto Casolari、Fulvia Felluga、Vincenzo Frenna、Franco Ghelfi、Ugo M. Pagnoni、Andrew F. Parsons、Domenico Spinelli

  DOI：10.1016/j.tet.2010.11.025

  日期：2011.1

  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.