1-benzyl-3,4-dichloro-3-ethylhexahydro-1H-indol-2(3H)-one | 1264739-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-3,4-dichloro-3-ethylhexahydro-1H-indol-2(3H)-one
• 英文别名: 1-Benzyl-3,4-dichloro-3-ethyl-3a,4,5,6,7,7a-hexahydroindol-2-one
• CAS: 1264739-88-9
• 化学式: C₁₇H₂₁Cl₂NO
• 分子量: 326.266
• InChiKey: OOLAKIYBPJFPBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  1-benzyl-3,4-dichloro-3-ethylhexahydro-1H-indol-2(3H)-one 、 sodium methylate 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 以46%的产率得到rac-(4R,7aR)-1-benzyl-3-ethyl-4-methoxy-5,6,7,7a-tetrahydro-1H-indol-2(4H)-one
  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
• 作为产物：
  描述：

  N-benzyl-2,2-dichloro-N-cyclohex-2-en-1-ylbutanamide 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， 以92%的产率得到1-benzyl-3,4-dichloro-3-ethylhexahydro-1H-indol-2(3H)-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