N-(p-methoxyphenyl)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoimidoyl chloride | 193477-02-0

• 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-(p-methoxyphenyl)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoimidoyl chloride
• 英文别名: N-(p-Anisyl)perfluorooctanoimidoyl chloride
• CAS: 193477-02-0
• 化学式: C₁₅H₇ClF₁₅NO
• 分子量: 537.656
• InChiKey: VHELZPRSQSZFQK-ORXZFWEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  N-(p-methoxyphenyl)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoimidoyl chloride 在 lithium tri(t-butoxy)aluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到N-(8,8,8,7,7,6,6,5,5,4,4,3,3,2,2-pentadecafluorooctylidene)-p-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：

  全氟辛酸 、 甲氧苯胺 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 生成 N-(p-methoxyphenyl)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoimidoyl chloride
  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

• 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。
• One-pot synthesis of trifluoroacetimidoyl halides
  作者：Kenji Tamura、Hiromichi Mizukami、Kazuhiro Maeda、Hisayuki Watanabe、Kenji Uneyama

  DOI：10.1021/jo00053a011

  日期：1993.1

  Trifluoroacetimidoyl chlorides 1 were obtained in 80-90 % yields when a mixture of trifluoroacetic acid and a primary amine was heated in carbon tetrachloride in the presence of triphenylphosphine and triethylamine. The corresponding bromides 2 were obtained when carbon tetrabromide was used instead of carbon tetrachloride. Imidoyl iodides 3 were prepared by substitution of the chloro group of 1 by iodide ion in acetone.
• 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.