N-methyltrifluoroacetimidoyl chloride | 2991-72-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 亚胺酰卤
• 英文名称: N-methyltrifluoroacetimidoyl chloride
• 英文别名: N-Methyl-trifluoracetimidoyl-chlorid；N-methyl-2,2,2-trifluoro-acetimidoyl chloride；N-methyl-trifluoroacetimidoyl chloride；2,2,2-trifluoro-N-methylethanimidoyl chloride
• CAS: 2991-72-2
• 化学式: C₃H₃ClF₃N
• 分子量: 145.512
• InChiKey: RVRJNODYVXPLSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyltrifluoroacetimidoyl chloride 在 水 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以50%的产率得到N-甲基-2,2,2-三氟乙酰胺
  参考文献：
  名称：

  摘要：

  N-Substituted trifluoroacetimidoyl halides in ionic-type transformations readily undergo nucleophilic substitution and dehydrofluorination rather than 1,3-dehydrohalogenation to give nitrile ylides.

  DOI：

  10.1023/a:1013046804682
• 作为产物：
  描述：

  N-甲基-2,2,2-三氟乙酰胺 在 五氯化磷 作用下， 反应 3.0h， 以26%的产率得到N-methyltrifluoroacetimidoyl chloride
  参考文献：
  名称：

  摘要：

  N-Substituted trifluoroacetimidoyl halides in ionic-type transformations readily undergo nucleophilic substitution and dehydrofluorination rather than 1,3-dehydrohalogenation to give nitrile ylides.

  DOI：

  10.1023/a:1013046804682

文献信息

• 1-Fluoroalkyl-prop-2-yne 1-imines and 1-iminium salts as building blocks: A new synthesis of α-(trifluoromethyl)pyrroles
  作者：Thomas Schneider、Bianca Seitz、Maximilian Schiwek、Gerhard Maas

  DOI：10.1016/j.jfluchem.2020.109567

  日期：2020.7

  induced cyclization of so-formed (3-aminoallenyl)phosphonium salts. While the mentioned alkynyl trifluoromethyl N-methyl-ketimines were obtained by copper-catalyzed cross-coupling of terminal alkynes and N-methyl-2,2,2-trifluoroacetimidoyl chloride, terminal alkynes and N-benzyl-2,2,2-trifluoroacetimidoyl chloride under the same reaction conditions furnished 2,3-disubstituted 5-CF3-pyrroles directly

  1氟烷基-丙-2-炔-1- Ñ，Ñ -dimethyliminium通过三氟甲磺酸酯，得到盐Ñ炔氟代-methylation Ñ -methylketimines。它们代表新颖的，由于氟代烷基的活化作用，是高反应性的炔属亚胺盐类。本文中，我们描述的CF的两步转换3取代的亚铵盐为1,4-二取代α-CF 3个-pyrroles通过迈克尔加成三苯基膦的和如此形成的（3- aminoallenyl）鏻盐的热诱导的环化。所述炔基三氟甲基N-甲基酮亚胺是通过末端炔烃和N的铜催化交叉偶联而获得的。-甲基-2,2,2-三氟乙酰亚胺基氯，末端炔烃和N-苄基-2,2,2-三氟乙酰亚胺基氯在相同的反应条件下直接提供2,3-二取代的5-CF 3-吡咯。
• Reactions of a 3‐Phenyl‐1‐trifluoromethyl‐prop‐2‐yne Iminium Salt with Furans, Thiophenes, and Pyrroles
  作者：Thomas Schneider、Georg Heinrich、Raphael Koch、Gerhard Maas

  DOI：10.1002/ejoc.202001577

  日期：2021.2.12

  iminium salt, N,N‐dimethyl 3‐phenyl‐1‐trifluoromethyl‐propyne iminium triflate, with electron‐rich heteroaromatic ring systems (furans, thiophenes, pyrroles) are reported. The 1‐CF3‐propyne iminium ion can act as a highly reactive ambident electrophile, giving rise to simple electrophilic heteroaromatic ring substitution products, and as a 1,3‐biselectrophile leading to C2+C3‐CF3 annulation products

  据报道，新型丙炔亚胺盐，N，N-二甲基3-苯基-1-三氟甲基-丙炔亚胺三氟甲磺酸盐与富电子杂芳族环系统（呋喃，噻吩，吡咯）的反应。1-CF 3-丙炔亚胺离子可充当高反应性的亲电体，从而产生简单的亲电杂芳族环取代产物，并成为导致C 2 + C 3 -CF 3环化产物的1,3-双亲电体。
• Sigmatropic isomerizations in azaallyl systems: XXI. Alkanimidoylphosphonates and their prototropic and phosphorotropic isomers
  作者：P. P. Onys’ko、T. V. Kim、E. I. Kiseleva、A. D. Sinitsa

  DOI：10.1007/s11176-005-0110-8

  日期：2004.12

  Synthetic procedures for alkanimidoylphosphoryl derivatives with α-hydrogen atoms in the N-alkyl radical are developed. Data on the effect of substituents at the carbon and phosphorus atoms on the facility of prototropic transitions in the C=N-C triad are summarized. The most facile proton transfer occurs in the N-benzyl derivatives, and the prototropic isomer is the more stable, the stronger the electron-acceptor power of the substituent at the sp 3-carbon atom of the azaallyl triad. The proton transfer in N-(α-phenethyl)-trifluoroacetimidoylphosphonates proceeds selectively, which allows preparation of enantiomerically enriched derivatives of α-aminotrifluoroethylphosphonic acid. A specific effect of substituents at the phosphorus atom on the prototropism attendant on phosphorylation of imidoyl chlorides is demonstrated.

  开发了含有α-氢原子的N-烷基自由基的烷基脲膦酰基衍生物的合成方法。总结了碳原子和磷原子上的取代基对C=N-C三元组中质子转移便利性的影响数据。在N-苄基衍生物中，质子转移最为容易，随着位于氮杂烯三元组的sp³碳原子上的取代基的电子受体能力增强，质子异构体愈加稳定。在N-(α-苯乙基)-三氟乙酰基脲膦酸酯中，质子转移选择性进行，这使得能够制备富含对映体的α-氨基三氟乙基膦酸的衍生物。证实了磷原子上取代基对氯脲酰化反应中伴随的质子转移的特定影响。
• Reactions of N-alkyl- and N-aryltrihalogenoacetamides with phosphorus pentachloride
  作者：A. D. Sinitsa、A. A. Shalimov、A. M. Nesterenko、D. M. Malenko

  DOI：10.1007/s11172-005-0316-2

  日期：2005.3

  the study of reactions of N-alkyl- and N-aryltrihalogenoacetamides with PCl5, it was demonstrated for the first time that 3-alkyl(aryl)-2,2,2,4 tetrachloro-4-trihalomethyl-1,3,2-λ5-oxazaphosphetanes are intermediates in the synthesis of trihaloacetimidoyl chlorides. According to quantum-chemical calculations, acyclic N-tetrachlorophosphoranes, which are the primary products in the reactions of trihaloacetamides

  在 N-烷基-和 N-芳基三卤代乙酰胺与 PCl5 反应的研究中，首次证明了 3-烷基（芳基）-2,2,2,4 四氯-4-三卤甲基-1,3,2 -λ5-oxazaphosphetanes 是合成三卤代乙酰亚氨基酰氯的中间体。根据量子化学计算，三卤乙酰胺与 PCl5 反应的主要产物无环 N-四氯正膦快速环化为相应的磷酸酯，随后 1,3- 氯代迁移产生具有五配位 P 的氧氮杂膦原子。
• Malenko, D. M.; Nesterova, L. I.; Pirozhenko, V. V., Russian Journal of General Chemistry, 1994, vol. 64, # 5.2, p. 785 - 786
  作者：Malenko, D. M.、Nesterova, L. I.、Pirozhenko, V. V.、Sinitsa, A. D.

  DOI：——

  日期：——