N-(4-chlorophenyl)diethylphosphonoacetamide | 153567-85-2

• 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-(4-chlorophenyl)diethylphosphonoacetamide
• 英文别名: N-(4-chlorophenyl)-2-diethoxyphosphorylacetamide
• CAS: 153567-85-2
• 化学式: C₁₂H₁₇ClNO₄P
• 分子量: 305.698
• InChiKey: YAIUQNAUQXXEHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)diethylphosphonoacetamide 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以52%的产率得到[N-(4-chlorophenyl)carbamoyl]methylphosphonic acid
  参考文献：
  名称：

  Plant-growth-regulatingN-(phosphonoacetyl)amines

  摘要：

  AbstractA series of N‐(phosphonacetyl)amine derivatives were synthesized and screened for plant‐growth regulating activity on Lepidium sativum L. and Cucumis sativus L. Aromatic N‐(phosphonoacetyl)amines. which may be considered as possible analogues of N‐acylaniline herbicides obtained by replacement of their acyl group by the phosphonacetyl moiety, exhibited significant or moderate herbicidal activity. In contrast, N‐(phosphonoacetyl)amino acids and N‐(phosphonoacetyl)aminophosphonic acids promoted the growth of L. sativum and C. sativus roots.

  DOI：

  10.1002/ps.2780400110
• 作为产物：
  描述：

  N-(4-氯苯基)-2-氯乙酰胺 、 亚磷酸三乙酯 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以92%的产率得到N-(4-chlorophenyl)diethylphosphonoacetamide
  参考文献：
  名称：

  Microwave-Enhanced Synthesis of Phosphonoacetamides

  摘要：

  An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.

  DOI：

  10.1080/00397911.2010.530377

文献信息

• Plant-growth-regulating<i>N</i>-(phosphonoacetyl)amines
  作者：Piotr Wieczorek、Dorota Miliszkiewicz、Barbara Lejczak、Miroslaw Soroka、Pawel Kafarski

  DOI：10.1002/ps.2780400110

  日期：1994.1

  AbstractA series of N‐(phosphonacetyl)amine derivatives were synthesized and screened for plant‐growth regulating activity on Lepidium sativum L. and Cucumis sativus L. Aromatic N‐(phosphonoacetyl)amines. which may be considered as possible analogues of N‐acylaniline herbicides obtained by replacement of their acyl group by the phosphonacetyl moiety, exhibited significant or moderate herbicidal activity. In contrast, N‐(phosphonoacetyl)amino acids and N‐(phosphonoacetyl)aminophosphonic acids promoted the growth of L. sativum and C. sativus roots.
• Microwave-Enhanced Synthesis of Phosphonoacetamides
  作者：Nadia Gruber、María C. Mollo、Mariana Zani、Liliana R. Orelli

  DOI：10.1080/00397911.2010.530377

  日期：2012.3.1

  An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.