P-iso-propyl-N,N-diethyl-N',N'-dimethylphosphorigsaeurediamid | 23685-52-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: P-iso-propyl-N,N-diethyl-N',N'-dimethylphosphorigsaeurediamid
• 英文别名: N-[dimethylamino(propan-2-yl)phosphoryl]-N-ethylethanamine
• CAS: 23685-52-1
• 化学式: C₉H₂₃N₂OP
• 分子量: 206.268
• InChiKey: UWVYDYKNAVIGRX-UHFFFAOYSA-N

物化性质

• 沸点：
  83-85 °C(Press: 0.15 Torr)
• 密度：
  0.9665 g/cm3(Temp: 26 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  isopropyl-phosphonic acid-chloride dimethylamide 、 二乙胺 生成 P-iso-propyl-N,N-diethyl-N',N'-dimethylphosphorigsaeurediamid
  参考文献：
  名称：

  Razvodovskaya,L.V. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 1230 - 1232

  摘要：

  DOI：

文献信息

• An alkylphosphonyl nucleophilic substitution reaction that proceeds by an elimination–addition mechanism with an alkylidineoxophosphorane (phosphene) intermediate
  作者：Martin J. P. Harger、Barbara T. Hurman

  DOI：10.1039/c39950001701

  日期：——

  For the phosphonamidic chloride R2CHP(O)(NEt2) Cl having R2CH = 9-fluorenyl, substitution at phosphorus is unexpectedly fast with Et2NH as the nucleophile, and discriminates less than is usual between competing Me2NH and Et2NH nucleophiles; such behaviour is consistent with an elimination-addition mechanism and a fluorenylidineoxophosphorane intermediate 8.

  对于具有R 2 CH = 9-芴基的膦酰氯氯化物R 2 CHP（O）（NEt 2）Cl，用Et 2 NH作为亲核试剂，磷的取代出乎意料地快，并且与竞争的Me 2 NH和Et 2 NH亲核试剂；这样的行为与消除加成机理和芴基氧代次膦酸酯中间体8是一致的。
• Elimination–addition with alkylidineoxophosphorane (phosphene) intermediates in nucleophilic substitution at PO centres: fluoren-9-ylphosphonamidic chlorides with amine nucleophiles 1
  作者：Martin J. P. Harger、Barbara T. Hurman

  DOI：10.1039/a800683k

  日期：——

  Compared with Me2CHP(O)(NEt2)Cl, the fluorenyl compound R2CHP(O)(NEt2)Cl (R2CH = fluoren-9-yl) shows remarkably high reactivity in nucleophilic substitution with Et2NH. Substitution is catalysed by base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)} and shows little discrimination between competing Me2NH and Et2NH. These characteristics point to an elimination–addition (EA) mechanism with a reactive phosphene intermediate [R2CP(O)NEt2]. When Et2ND is the nucleophile, H–D exchange at the α carbon atom occurs much more quickly than substitution. This suggests that the elimination stage of the EA mechanism is reversible E1cB.

  与 Me2CHP(O)(NEt2)Cl 相比，芴基化合物 R2CHP(O)(NEt2)Cl （R2CHÂ =Â fluoren-9-yl）在与 Et2NH 的亲核取代中显示出极高的反应活性。在碱 1,8-二氮杂双环[5.4.0]十一-7-烯（DBU）} 的催化下进行置换，在竞争的 Me2NH 和 Et2NH 之间几乎没有区别。这些特征表明，这种消去加成（EA）机理带有一个活性磷烯中间体[R2CP(O)NEt2]。当 Et2ND 为亲核体时，δ 碳原子上的 HâD 交换发生得比取代快得多。这表明 EA 机制的消去阶段是可逆的 E1cB。
• Razvodovskaya,L.V. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 1230 - 1232
  作者：Razvodovskaya,L.V. et al.

  DOI：——

  日期：——