Ethanimidoyl chloride, 2-chloro-2,2-difluoro-N-(4-methoxyphenyl)-, (1Z)- | 193477-03-1

• 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: Ethanimidoyl chloride, 2-chloro-2,2-difluoro-N-(4-methoxyphenyl)-, (1Z)-
• 英文别名: 2-chloro-N-(p-methoxyphenyl)-2,2-difluoroacetimidoyl chloride
• CAS: 193477-03-1
• 化学式: C₉H₇Cl₂F₂NO
• 分子量: 254.063
• InChiKey: LYCUXUDSYSARHZ-ZSOIEALJSA-N

物化性质

• 沸点：
  263.4±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Ethanimidoyl chloride, 2-chloro-2,2-difluoro-N-(4-methoxyphenyl)-, (1Z)- 在 lithium tri(t-butoxy)aluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到(E)-N-(2-chloro-2,2-difluoroethylidene)-4-methoxyaniline
  参考文献：
  名称：

  Facile Preparation of Polyfluoroalkylated Aldimines from Polyfluoroalkanoic Acids

  摘要：

  通过用 LTBA（三叔丁氧基氢化铝锂）还原多氟烷基亚胺酰氯，制备了多氟烷基醛亚胺。

  DOI：

  10.1055/s-2007-966055
• 作为产物：
  描述：

  甲氧苯胺 、 二氟氯乙酸 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 生成 Ethanimidoyl chloride, 2-chloro-2,2-difluoro-N-(4-methoxyphenyl)-, (1Z)-
  参考文献：
  名称：

  Facile Preparation of Polyfluoroalkylated Aldimines from Polyfluoroalkanoic Acids

  摘要：

  通过用 LTBA（三叔丁氧基氢化铝锂）还原多氟烷基亚胺酰氯，制备了多氟烷基醛亚胺。

  DOI：

  10.1055/s-2007-966055

文献信息

• Selective Formal Transesterification of Fluorinated 2-(Trimethylsilyl)ethyl α-Imino Esters Mediated by TBAF
  作者：Santos Fustero、María Sánchez-Roselló、Vanessa Rodrigo、Amador García、Silvia Catalán、Carlos del Pozo

  DOI：10.1021/jo800567a

  日期：2008.7.1

  The scope of the transesterification reaction between β-fluorinated α-imino esters and various electrophiles in the presence of TBAF as fluorine source is described. The reaction is highly selective for alkyl iodides, bromides, and mesylates, while alkyl chlorides react at a significantly slower rate and tosylates do not react under the reaction conditions. This methodology represents a simple and

  描述了在TBAF作为氟源存在下，β-氟化α-亚氨基酯与各种亲电试剂之间的酯交换反应的范围。该反应对烷基碘，溴化物和甲磺酸酯具有很高的选择性，而烷基氯化物的反应速度明显慢得多，而甲苯磺酸酯在反应条件下不反应。该方法学是制备多种氟化α-亚氨基酯的一种简单而有用的替代方法。
• A new and general synthesis of N-substituted fluorinated β-iminosulfoxides
  作者：Santos Fustero、Antonio Navarro、Amparo Asensio

  DOI：10.1016/s0040-4039(97)01051-4

  日期：1997.7

  Reaction of fluorinated imidoyl chlorides 1 with lithium enolates of chiral non-racemic methyl p-tolyl sulfoxide or racemic methyl phenyl sulfoxide 2 gave N-substituted γ-fluorinated β-iminosulfoxides 3 in excellent yields as the major tautomer with Z geometry.

  氟化亚氨基氯化物1与手性非外消旋甲基对甲苯基亚砜或外消旋甲基苯基亚砜2的烯醇锂的反应以优异的产率得到N-取代的γ-氟化的β-亚氨基亚砜3，其为具有Z几何形状的主要互变异构体。
• N-Substituted β-Enamino Acid Derivatives: A New Approach to Fluorinated β-Enamino Esters
  作者：Santos Fustero、Belén Pina、Antonio Simón-Fuentes

  DOI：10.1016/s0040-4039(97)01549-9

  日期：1997.9

  Reaction of fluorinated imidoyl chlorides 1 with lithium ester enolates 2 gave N-substituted γ-fluorinated β-enamino and/or β-imino esters 4 in good to excellent yields. β-Enamino esters were obtained exclusively as Z isomers. © 1997 Published by Elsevier Science Ltd.

  氟化亚氨基氯化物1与酯烯醇锂2的反应以良好的至优异的产率得到N-取代的γ-氟化的β-烯氨基和/或β-亚氨基酯4。β-烯氨基酯仅作为Z异构体获得。©1997由Elsevier Science Ltd发布。
• New Strategies for the Synthesis of Fluorinated Vinylogous Amidines and β-Enamino Ketones
  作者：Santos Fustero、Marta García de la Torre、Belén Pina、Antonio Simón Fuentes

  DOI：10.1021/jo990392w

  日期：1999.7.1

  imidoyl chlorides 3 with ketimines 1a provides fluorinated 1,3-diimines, which were exclusively isolated as vinylogous amidine tautomers 2beta, with good yields. Fluorinated beta-enamino ketones 4 are obtained by regioselective hydrolysis of 2. Complementary methods for the synthesis of regioisomeric beta-enamino ketones 4 and 5 are also reported. These methods include the reaction of azaenolates of

  氟化亚氨酰氯3与酮亚胺1a的反应提供了氟化1，3-二亚胺，其被单独分离为乙烯基og互变异构体2beta，具有良好的收率。氟化的β-烯胺酮4是通过2的区域选择性水解而获得的。还报道了用于合成区域异构的β-烯胺酮4和5的补充方法。这些方法包括酮亚胺的氮杂酸酯与氟化酯6的反应以及酮烯酸酯与氟化亚氨酰氯3的反应。还测试了这些体系在水解反应中的行为。
• Two Practical and Efficient Approaches to Fluorinated and Nonfluorinated Chiral β-Imino Sulfoxides
  作者：Santos Fustero、Antonio Navarro、Belén Pina、Amparo Asensio、Pierfrancesco Bravo、Marcello Crucianelli、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/jo980336f

  日期：1998.9.1

  Reaction of fluorinated and nonfluorinated N-substituted imidoyl chlorides 1 with lithium derivatives of enantiopure methyl p-tolyl sulfoxide 2a (or racemic methyl phenyl sulfoxide 2b) gave a wi;ie variety of chiral N-substituted beta-imino sulfoxides 4 in good to excellent yields. The title compounds (R)-4 were also prepared by aza-Wittig reaction of gamma-fluoro-beta-keto sulfoxides (R)-5 and N-aryl iminophosphoranes 6. The imino-enamino equilibrium was studied, showing, in all instances, the imino form as the predominant tautomer independent of the nature of the N-substituent. The configuration of the C=N double bond was found to be Z for both N-alkyl and N-aryl derivatives on the basis of H-1 NMR NOE difference experiments performed over several compounds. Ab initio calculations (HF/6-31G*) carried out on several representative examples of 1 and 4 are, in general, consistent with the experimental results.