N-allyl-2,2-dichloroacetanilide | 39089-61-7

• 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-2,2-dichloroacetanilide
• 英文别名: N-allyl-α,α-dichloroacetanilide；N-allyl-2,2-dichloro-N-phenylacetamide；2,2-dichloro-N-phenyl-N-prop-2-enylacetamide
• CAS: 39089-61-7
• 化学式: C₁₁H₁₁Cl₂NO
• 分子量: 244.12
• InChiKey: LRRGJJCWYDTGAL-UHFFFAOYSA-N

物化性质

• 沸点：
  307.1±42.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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-2,2-dichloroacetanilide 生成 N-allyl-N-phenylacetamide
  参考文献：
  名称：

  SATO, TATSUNORI;WADA, YASUKO;NISHIMOTO, MAMI;ISHIBASHI, HIROYUKI;IKEDA, M+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 879-886

  摘要：

  DOI：
• 作为产物：
  描述：

  N-烯丙基苯胺 、 二氯乙酰氯 以86%的产率得到N-allyl-2,2-dichloroacetanilide
  参考文献：
  名称：

  Sato, Tatsunori; Wada, Yasuko; Nishimoto, Mami, Journal of the Chemical Society. Perkin transactions I, 1989, p. 879 - 886

  摘要：

  DOI：

文献信息

• Ruthenium vs. Osmium Complexes as Catalysts for Atom Transfer Radical Addition Reactions
  作者：Mariano A. Fernández‐Zúmel、Gregor Kiefer、Katrin Thommes、Rosario Scopelliti、Kay Severin

  DOI：10.1002/ejic.201000388

  日期：2010.8

  evaluated for atom transfer radical addition (ATRA) and cyclization (ATRC) reactions. The Os complex enabled these reactions to be performed with similar efficiency as that of the analogous Ru complex [Cp*RuCl2(PPh3)]. The olefin complex [Cp*OsBr(H2C=CHPh)(PPh3)] was obtained by reduction of [Cp*OsBr2(PPh3)] with Mg in the presence of an excess of styrene, whereas an analogous Ru complex was not observed

  [Cp*OsBr2(PPh3)] 与 Mg 结合的催化活性已针对原子转移自由基加成 (ATRA) 和环化 (ATRC) 反应进行了评估。Os 配合物使这些反应能够以与类似的 Ru 配合物 [Cp*RuCl2(PPh3)] 相似的效率进行。烯烃配合物 [Cp*OsBr(H2C=CHPh)(PPh3)] 是通过在过量苯乙烯存在下用镁还原 [Cp*OsBr2(PPh3)] 获得的，而没有观察到类似的 Ru 配合物。动力学研究表明 Os 的烯烃配合物可以在催化条件下形成。
• Olefin Cyclopropanation by a Sequential Atom-Transfer Radical Addition and Dechlorination in the Presence of a Ruthenium Catalyst
  作者：Katrin Thommes、Gregor Kiefer、Rosario Scopelliti、Kay Severin

  DOI：10.1002/anie.200904278

  日期：2009.10.12

  Without diazo: The reductive coupling of olefins with dichloro compounds in the presence of a ruthenium catalyst and magnesium gives cyclopropanes in good yield (see scheme).

  在没有重氮的情况下：在钌催化剂和镁的存在下，烯烃与二氯化合物的还原偶联以良好的收率得到环丙烷（参见方案）。
• Olefin Cyclopropanations via Sequential Atom Transfer Radical Addition-Dechlorination Reactions
  作者：Katrin Thommes、Kay Severin

  DOI：10.2533/chimia.2010.188

  日期：——

  In organic synthesis, cyclopropanation reactions are often performed with Simmons–Smith-type reagents or by transition metal catalyzed reactions of olefins with diazo compounds. A novel method for the synthesis of substituted cyclopropanes is described that is based on a two-step reaction sequence. Olefins are reacted with 1,1'-dichlorides in a Ru-catalyzed atom transfer radical addition (ATRA) process and the resulting 1,3-dichlorides are directly converted into cyclopropanes by reductive coupling with magnesium. This one-pot procedure is applicable to a variety of substrates and can be performed in an inter- or intramolecular fashion.

  在有机合成中，环丙烷化反应通常使用Simmons-Smith类型试剂进行，或者通过过渡金属催化的烯烃与重氮化合物的反应进行。描述了一种基于两步反应序列的合成取代环丙烷的新方法。烯烃通过Ru催化的原子转移自由基加成（ATRA）过程与1,1'-二氯化物反应，生成的1,3-二氯化物通过与镁的还原偶联直接转化为环丙烷。这种一锅法适用于各种底物，并可以以分子间或分子内的方式进行。
• A coordinatively unsaturated ruthenium methoxide as a highly effective catalyst for the halogen atom-transfer radical cyclization of N-allyl dichloroacetamides and related reactions
  作者：Yukihiro Motoyama、Shiori Hanada、Kazuya Shimamoto、Hideo Nagashima

  DOI：10.1016/j.tet.2006.01.011

  日期：2006.3

  Atom-transfer radical cyclization (ATRC) catalyzed by coordinatively unsaturated ruthenium alkoxides 4, [(eta(5)-C5Me5)-Ru(OR)](2), is investigated, and ruthenium methoxide 4a (R=Me) is found to exhibit excellent catalytic activity for the cyclization of N-allyl-alpha,alpha-dichloroacetamides at ambient temperature. Addition of some amounts of two-electron donor ligands such as pyridine and triphenylphosphine improves the catalyst efficiency to afford the corresponding gamma-lactams in high yields. The high catalytic activity of this catalyst system enables to control the diastereoselectivity of this 5-exo cyclization kinetically. The present 4a/pyridine system is also effective for the 4-exo cyclization of N-vinylacetarnides to afford the corresponding beta-lactams in quantitative yields. The 4a/pyridine system is also active towards the ATRP of methyl methacrylate (MMA) at room temperature to afford the poly(MMA) with narrow molecular weight distributions (M-w/M-n = 1.2) at the initial stage. (c) 2006 Elsevier Ltd. All rights reserved.
• Tseng, C. K.; Teach, E. G.; Simons, R. W., Synthetic Communications, 1984, vol. 14, # 11, p. 1027 - 1032
  作者：Tseng, C. K.、Teach, E. G.、Simons, R. W.

  DOI：——

  日期：——