N-methyl-N-(1-methyl-2-propen)trichloroacetamide | 145593-43-7

• 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: N-methyl-N-(1-methyl-2-propen)trichloroacetamide
• 英文别名: N-but-3-en-2-yl-2,2,2-trichloro-N-methylacetamide
• CAS: 145593-43-7
• 化学式: C₇H₁₀Cl₃NO
• 分子量: 230.522
• InChiKey: YBUZRXOTGGQCDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  228.1±40.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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-methyl-N-(1-methyl-2-propen)trichloroacetamide 在 Cu{1,2-bis[(2-pyridyl)ethynyl]benzene}Cl 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 、 (4S,5R)-3,3-dichloro-4-(chloromethyl)-1,5-dimethylpyrrolidin-2-one
  参考文献：
  名称：

  具有新型π-共轭1,2-双(2-吡啶基乙炔基)苯配体的铜(I)螯合物：合成、结构和反应性

  摘要：

  新的 π 共轭氮配体、1,2-双（2-吡啶基乙炔基）苯和它们的 Cu(I) 配合物已被合成并进行结构表征：还研究了配合物对自由基环化的反应性。

  DOI：

  10.1246/cl.2001.1230
• 作为产物：
  描述：

  N-(1-buten-3-yl)formamide 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 N-methyl-N-(1-methyl-2-propen)trichloroacetamide
  参考文献：
  名称：

  Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams

  摘要：

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.

  DOI：

  10.1021/jo00054a034

文献信息

• Copper(I) Chelate Complexes with Novel<i>π</i>-Conjugated 1,2-Bis(2-pyridylethynyl)benzene Ligands: Synthesis, Structure, and Reactivity
  作者：Tomikazu Kawano、Jun Kuwana、Tatsuji Shinomaru、Chong-Xu Du、Ikuo Ueda

  DOI：10.1246/cl.2001.1230

  日期：2001.12

  Novel π-conjugated nitrogen ligands, 1,2-bis(2-pyridylethynyl)benzenes, and their Cu(I) complexes have been synthesized and structurally characterized: the reactivity of the complexes for radical cyclization has also been examined.

  新的 π 共轭氮配体、1,2-双（2-吡啶基乙炔基）苯和它们的 Cu(I) 配合物已被合成并进行结构表征：还研究了配合物对自由基环化的反应性。
• Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams
  作者：Hideo Nagashima、Nobuyasu Ozaki、Masayuki Ishii、Koji Seki、Masayoshi Washiyama、Kenji Itoh

  DOI：10.1021/jo00054a034

  日期：1993.1

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.