N,N,N’,N’-tetraethyl-P-phenyl-phosphonic diamide | 4519-35-1

• 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,N,N’,N’-tetraethyl-P-phenyl-phosphonic diamide
• 英文别名: phenylphosphonic acid bis(N,N-diethylamide)；phenylphosphonic acid bis(diethylamide)；phenylphosphonic tetraethyldiamide；N,N,N',N'-tetraethyl-P-phenyl-phosphonic diamide；Phosphonic diamide, N,N,N',N'-tetraethyl-P-phenyl-；N-[diethylamino(phenyl)phosphoryl]-N-ethylethanamine
• CAS: 4519-35-1
• 化学式: C₁₄H₂₅N₂OP
• 分子量: 268.339
• InChiKey: KPGVXVMXRHCDQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N,N’,N’-tetraethyl-P-phenyl-phosphonic diamide 在 仲丁基锂 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 以78%的产率得到N,N,N’,N’-tetraethyl-P-(2-iodophenyl)-phosphonic diamide
  参考文献：
  名称：

  螯合辅助中断的铜（I）催化的叠氮化物–炔烃–叠氮化物多米诺反应：完全取代的5-Triazenyl-1,2,3-三唑的合成

  摘要：

  我们描述了通过无配位的多米诺铜（I）催化的叠氮化物-炔烃-叠氮化物螯合带有NP的芳基叠氮化物的方法合成1,4-（二取代）-5-三嗪烯-1,2,3-三唑邻位的O，P═O和SO 3 H基团带有各种乙炔。DFT计算表明，铜螯合是叠氮化物拦截CuAAC中间体的关键因素。催化物质的晶体结构已经通过X射线衍射确定。

  DOI：

  10.1021/acs.orglett.0c03838
• 作为产物：
  描述：

  双(二乙胺)苯膦 在 双氧水 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以8.887 g的产率得到N,N,N’,N’-tetraethyl-P-phenyl-phosphonic diamide
  参考文献：
  名称：

  芳基磷酰胺在桦木还原条件下的反应性

  摘要：

  已经在液氨中与碱金属溶液的反应中测试了几类芳基磷酰胺。这种反应的结果取决于起始材料的结构。通常，两个过程——桦木还原或对芳基键的断裂——可以起作用。二芳基次膦酰胺倾向于进行双桦木还原反应以得到双（环己二烯基）次膦酰胺。

  DOI：

  10.1002/ejoc.201300344

文献信息

• Phosphoryl-Related Directing Groups in Rhodium(III) Catalysis: A General Strategy to Diverse P-Containing Frameworks
  作者：Dongbing Zhao、Corinna Nimphius、Matthew Lindale、Frank Glorius

  DOI：10.1021/ol402053n

  日期：2013.9.6

  Herein, a rhodium(III)-catalyzed oxidative C–H activation of simple arylphosphonates and phosphonamides with subsequent coupling with alkenes (olefination), internal alkynes (hydroarylation and oxidative cyclization), or simple arenes to give access to diverse P-containing functional frameworks is reported.

  在此，铑（III）催化简单的芳基膦酸酯和膦酰胺的氧化CH活化，随后与烯烃（烯烃化），内部炔烃（加氢芳基化和氧化环化）或简单的芳烃偶联，从而可以使用各种含P的功能性骨架被报道。
• Evaluation of a P,N-ligated iridium(I) catalyst in hydrogen isotope exchange reactions of aryl and heteroaryl compounds
  作者：Mégane Valero、Annina Burhop、Kristof Jess、Remo Weck、Matthias Tamm、Jens Atzrodt、Volker Derdau

  DOI：10.1002/jlcr.3595

  日期：2018.4

  We have developed a novel and efficient iridium-catalyzed hydrogen isotope exchange reaction method with secondary and tertiary sulfonamides at ambient temperatures. Furthermore N-oxides and phosphonamides have been successfully applied in hydrogen isotope exchange reactions with moderate to excellent deuterium introduction.

  我们开发了一种新型高效的铱催化氢同位素交换反应方法，在室温下使用仲磺酰胺和叔磺酰胺。此外，N-氧化物和膦酰胺已成功应用于氢同位素交换反应，并具有中等至极好的氘引入。
• Hydrogen-Bond-Controlled Formal <i>Meta</i>-Selective C–H Transformations and Regioselective Synthesis of Multisubstituted Aromatic Compounds
  作者：Jie Wang、Takeru Torigoe、Yoichiro Kuninobu

  DOI：10.1021/acs.orglett.9b00030

  日期：2019.3.1

  The meta-selective introduction of functional groups into aromatic substrates was successfully achieved by hydrogen-bond-controlled meta-selective C–H borylation and successive conversion of the boryl group to other functional groups. By this method a wide range of functional groups could be introduced without isolation of the borylated intermediates. The desired meta-functionalized aromatic products

  所述元-选择性官能团引入到芳族底物已经成功地由氢键控制实现的元-选择性C-H硼化和氧硼基为其它官能团的连续转化。通过这种方法，可以引入广泛的官能团而无需分离硼化的中间体。所期望的元-官能化在一锅的方式获得即使是在克规模的芳族产物。还实现了多取代芳族化合物的区域选择性合成。
• A new synthesis of π-electron conjugated phosphonates and phosphonic bis(diethylamides) and their SHG activities
  作者：Takuji Ogawa、Naoya Usuki、Noboru Ono

  DOI：10.1039/a709082j

  日期：——

  A series of vinylic and arylic phosphonates and phosphonic bis(diethylamides) were prepared by copper promoted substitution of the corresponding bromides. These π-electron conjugated phosphonates and phosphonic bis(diethylamides) were investigated to elucidate their optical and second harmonic generation (SHG) properties; it was found that diphenyl 2-(4-dimethylaminophenyl)ethenylphosphonate exhibited strong SHG activity, the efficiency being 13 times greater than that of urea.

  通过铜催化的相应溴化物的取代反应，制备了一系列乙烯基和芳基膦酸盐及双（二乙基酰胺）膦酸。研究了这些共轭的磷酸盐和双（二乙基酰胺）膦酸的光学性质和二次谐波产生（SHG）特性；发现二苯基2-（4-二甲氨基苯基）乙烯基膦酸盐具有强烈的SHG活性，效率比尿素高13倍。
• BIPYRIDYL COMPOUND
  申请人：JAPAN SCIENCE AND TECHNOLOGY AGENCY

  公开号：US20170001960A1

  公开（公告）日：2017-01-05

  There are provided a compound capable of being a novel ligand allowing regioselective borylation to be performed in the aromatic borylation reaction, and a catalyst using the same compound. There is provided a bipyridyl compound represented by a general formula ( 1 ): (wherein A represents a single bond, a vinylene group or an ethynylene group; X represents an oxygen atom or a sulfur atom; n pieces of R 1 may be the same or different, and R 1 represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted amino group, a cyano group, a nitro group, or an alkoxycarbonyl group, or two adjacent R 1 may form a saturated or unsaturated ring structure optionally containing a hetero atom together with the carbon atoms bonded to the two R 1 ; R 2 represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group; and n represents a number of 1 to 4 ).

  提供了一种化合物，可以作为一种新型配体，在芳基硼化反应中实现区域选择性硼化，并提供了使用该化合物的催化剂。提供了一种由通式（1）表示的双吡啶化合物：（其中A代表单键、乙烯基或乙炔基；X代表氧原子或硫原子；n个R1可能相同或不同，R1代表氢原子、卤素原子、可选择取代的碳氢基团、可选择取代的烷氧基团、可选择取代的芳氧基团、可选择取代的氨基团、氰基、亚硝基或烷氧羰基，或者两个相邻的R1可能形成一个饱和或不饱和环结构，该环结构与两个R1键合的碳原子一起可能含有一个杂原子；R2代表氢原子、可选择取代的碳氢基团、可选择取代的烷氧基团或可选择取代的芳氧基团；n代表1到4的数字）。

表征谱图