diisopropyl-N-(4-chlorophenyl)phosphoramidate | 91638-89-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: diisopropyl-N-(4-chlorophenyl)phosphoramidate
• 英文别名: 4-chloro-N-di(propan-2-yloxy)phosphorylaniline
• CAS: 91638-89-0
• 化学式: C₁₂H₁₉ClNO₃P
• 分子量: 291.715
• InChiKey: ZAMWHZCMOUAECH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  亚磷酸二异丙酯 、 对氯苯胺 在 copper(I) bromide 作用下， 以 乙酸乙酯 为溶剂， 反应 22.0h， 以63%的产率得到diisopropyl-N-(4-chlorophenyl)phosphoramidate
  参考文献：
  名称：

  Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates

  摘要：

  An efficient method to generate N-P bonds directly from N-H and P-H bonds is described. Various arylamines and dialkylphosphites were directly oxidized to the corresponding N-arylphosphoramidates at room temperature in moderate to good yields by using an inexpensive catalyst-oxidant (CuBr/air) system. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.006

文献信息

• Kinetics and Mechanism of the Anilinolysis of Diisopropyl Chlorophosphate in Acetonitrile
  作者：Md. Ehtesham Ul Hoque、Hai-Whang Lee

  DOI：10.5012/bkcs.2011.32.9.3245

  日期：2011.9.20

  anilines () and deuterated anilines () are investigated kinetically in acetonitrile at . The anilinolysis rate of 3 is rather slow to be rationalized by the conventional stereoelectronic effects. The obtained deuterium kinetic isotope effects (DKIEs; ) are secondary inverse ( = 0.71-0.95) with maximum magnitude at X = H.A concerted mechanism involving predominant backside nucleophilic attack is proposed on

  氯磷酸二异丙酯 (3) 与取代苯胺 () 和氘代苯胺 () 的亲核取代反应在乙腈中进行了动力学研究。3 的苯胺分解速率相当慢，无法通过传统的立体电子效应合理化。所获得的氘动力学同位素效应 (DKIEs;) 是二次反演 (= 0.71-0.95)，在 X = HA 处具有最大值，在二次反演 DKIE 的基础上提出了涉及主要背面亲核攻击的协同机制。
• Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates
  作者：Gao Wang、Qing-Ying Yu、Shan-Yong Chen、Xiao-Qi Yu

  DOI：10.1016/j.tetlet.2013.09.006

  日期：2013.11

  An efficient method to generate N-P bonds directly from N-H and P-H bonds is described. Various arylamines and dialkylphosphites were directly oxidized to the corresponding N-arylphosphoramidates at room temperature in moderate to good yields by using an inexpensive catalyst-oxidant (CuBr/air) system. (C) 2013 Elsevier Ltd. All rights reserved.
• Optimization of Phosphoramidates Synthetic Conditions
  作者：N. D. Khan、H. Khan

  DOI：10.1134/s1070363218030271

  日期：2018.3

  An optimized catalytic oxidative cost effective process of dehydrogenative coupling of diisopropyl phosphite with arylamines led to formation of the corresponding phosphoramidates. Structures of products were elucidated from NMR and ESI-MS data.