3-{[(P,P-diphenyl)(N-diphenylphosphoryl)phosphazenyl]methyl}-4-nitrobenzonitrile

• 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: 3-{[(P,P-diphenyl)(N-diphenylphosphoryl)phosphazenyl]methyl}-4-nitrobenzonitrile
• 英文别名: 3-{[P,P-diphenyl-N-(diphenylphosphono)aminophosphonyl]methyl}-4-nitrobenzene；3-[[Diphenoxyphosphorylimino(diphenyl)-lambda5-phosphanyl]methyl]-4-nitrobenzonitrile；3-[[diphenoxyphosphorylimino(diphenyl)-λ5-phosphanyl]methyl]-4-nitrobenzonitrile
• 化学式: C₃₂H₂₅N₃O₅P₂
• 分子量: 593.515
• InChiKey: VWIIHJFWXVGNEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  叠氮磷酸二苯酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 49.0h， 生成 3-{[(P,P-diphenyl)(N-diphenylphosphoryl)phosphazenyl]methyl}-4-nitrobenzonitrile
  参考文献：
  名称：

  Synthesis of 1,2-dihydro-1,3-diaza-2λ5,4λ5-2,4-diphosphorine 2-oxides

  摘要：

  The reaction of lithium (N-diphenylphosphoryl)phosphazenes with nitriles afforded 1,2-dihydro-1,3-diaza-2lambda(5),4lambda(5)-2,4-diphosphorine 2-oxides through a C-regioselective addition to the cyano linkage followed by in situ cyclocondensation. The new heterocycles 4:1 were designed to mimic thymine and are promising chemotherapeutic anticancer agents. As an exception, for p-nitrobenzonitrile a SNAr C, reaction was exclusively observed with the nucleophile entering in the ortho position of the nitro substituent in a process directed by the strong electron withdrawing effect of the NO2 group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00144-8

文献信息

• Regioselective functionalisation of nitrobenzene and benzonitrile derivatives via nucleophilic aromatic substitution of hydrogen by phosphorus-stabilized carbanions
  作者：Carmen M. Andújar Sánchez、Ma José Iglesias、Jesús García Lopez、Isidro J. Pérez Álvarez、Fernando López Ortiz

  DOI：10.1016/j.tet.2006.01.088

  日期：2006.4

  oxide groups by displacement of hydrogen of a variety of electron-deficient benzene derivatives is described. Lithium phosphazenes were the most suitable nucleophiles for the substitution of hydrogen in nitrobenzene and some ortho-, meta-, and para- substituted nitrobenzenes. Lithiated phosphine borane complexes produced efficiently the substitution of the hydrogen at the para position of a cyano group

  描述了通过由多种缺电子的苯衍生物的氢置换而使由N-磷酰基磷腈基，N-甲氧基羰基磷腈基，膦硼烷络合物和氧化膦基团稳定的阴离子反应合成P-苄基产物。磷腈锂是最适合取代硝基苯和一些邻位，间位和对位取代的硝基苯中的氢的亲核试剂。锂化的膦硼烷配合物有效地产生的氢的取代在对位氰基苯中氰基的位置，而乙基二苯基膦氧化物的阴离子会导致所有亲电试剂的复杂混合物。本文报道的方法代表了一种替代方法，可替代载气的亲核取代反应，该方法可使用在碳负离子中心不带有离去基团的磷稳定化的阴离子来合成苄基磷衍生物。