N,N-diethylamino phenylphosphonochloramidate | 17833-40-8

• 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-diethylamino phenylphosphonochloramidate
• 英文别名: N-[chloro(phenyl)phosphoryl]-N-ethylethanamine
• CAS: 17833-40-8
• 化学式: C₁₀H₁₅ClNOP
• 分子量: 231.662
• InChiKey: LMOOHGAVSHMYPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethylamino phenylphosphonochloramidate 在 盐酸 、 正丁基锂 、 四甲基乙二胺 、 氨 、 水 作用下， 以 四氢呋喃 、 正己烷 、 Petroleum ether 为溶剂， 反应 1.0h， 生成 diammonium thiophene-2,5-diylbis(phenylphosphinate)
  参考文献：
  名称：

  Crystal packing of ammonium salts of arylenebis(phenylphosphinic) acids

  摘要：

  首次表明噻吩-2,5-二基双(苯基次膦酸)铵盐的晶体堆积方式与1,4-亚苯基双(苯基次膦酸)二甲基铵盐的晶体堆积方式有显着差异。前一种晶体堆积是三层超分子夹层结构，由一层铵阳离子层隔开的两个阴离子层组成，而后一种盐的超分子组织基于通过氢键连接的阴离子和阳离子的交替层。

  DOI：

  10.1007/s11172-014-0411-3
• 作为产物：
  描述：

  苯膦酰二氯 、 二乙胺 在 三乙胺 作用下， 生成 N,N-diethylamino phenylphosphonochloramidate
  参考文献：
  名称：

  Microwave-Assisted Synthesis of N,N-Dialkyl-P-Alkylphosphonamidic Anhydrides

  摘要：

  A new rapid, efficient, solvent-free, microwave-assisted, and high-yielding method for the synthesis of N,N-dialkyl-P-alkylphosphonamidic anhydrides has been developed. The method involves the use of 4-dimethylaminopyridine and water under microwave irradiation. The reaction of N,N-dialkylaminoalkyl/phenyl phosphonochloridates 2a-h with 4-dimethylaminopyridine (DMAP) gave pyridinium salts, which were converted into N,N-dialkyl-P-alkylphosphonamidic anhydrides 4a-h.

  DOI：

  10.1080/10426500902953961

文献信息

• Surface-mediated synthesis of organophosphorus-based hydrazides using basic alumina
  作者：Kavita、P. Joshi、N. Sharma、Y. C. Joshi

  DOI：10.1139/v10-111

  日期：2010.10

  The surface-mediated synthesis of O-alkyl alkylphosphorohydrazides and N,N-dialkylamino alkylphosphorohydrazides from phosphoryl chlorides is described. The effect of the presence of chromatographic-grade Al₂O₃(basic) on the hydrazinolysis of a series of O-alkyl alkylphosphonic chlorides and N,N-dialkylamino alkylphosphonic chlorides has also been investigated. It was observed that higher yields of the less-hindered hydrazides were obtained

  本研究描述了以磷酰氯为原料，通过表面介导合成 O-烷基烷基磷酰肼和 N,N-二烷基氨基烷基磷酰肼的过程。此外，还研究了色谱级 Al2O3（碱性）的存在对一系列 O-烷基烷基膦酰氯和 N,N-二烷基氨基烷基膦酰氯肼解作用的影响。结果表明，获得的少阻肼的产率较高
• Synthesis and structure of ferrocenylphosphinic acids
  作者：Ruslan P. Shekurov、Vasili A. Miluykov、Daut R. Islamov、Dmitry B. Krivolapov、Olga N. Kataeva、Tatyana P. Gerasimova、Sergey A. Katsyuba、Gulnaz R. Nasybullina、Vitaliy V. Yanilkin、Oleg G. Sinyashin

  DOI：10.1016/j.jorganchem.2014.04.035

  日期：2014.9

  The series of ferrocenylphosphinic acids Fc(P(R)(O)(OH)) (1a–d) and ferrocene-1,1′-diyl-phosphinic acids Fc(P(R)(O)(OH))2 (2a–d) (R = H (a), Me (b), Et (c), Ph (d)) have been obtained and studied using X-ray single crystal diffraction, IR-spectroscopy and quantum chemistry. The intermolecular hydrogen bonding in 1a–d proceeds highly stereoselectively and results in formation of racemic conglomerate

  二茂铁基次膦酸Fc（P（R）（O）（OH））（1a - d）和二茂铁-1,1'-二基次膦酸Fc（P（R）（O）（OH））2（已经获得了2a - d）（R = H（a），Me（b），Et（c），Ph（d）），并使用X射线单晶衍射，IR光谱和量子化学进行了研究。1a - d中的分子间氢键高度立体选择性地进行，并导致1d的外消旋团聚体的形成。二取代酸2c - d的分子间和分子内氢键的形成取决于磷原子上的取代基。
• Supramolecular architecture of diammonium ferrocene-1,1′-diyldiphosphinates
  作者：R. P. Shekurov、A. I. Tufatullin、V. A. Milyukov、O. N. Kataeva、O. G. Sinyashin

  DOI：10.1007/s11172-014-0410-4

  日期：2014.1

  Diammonium ferrocene-1,1′-diyldi(H-phosphinate) (1) and diammonium ferrocene-1,1′-diylbis(phenylphosphinate) (2) were obtained for the first time and structurally characterized. Compound 1 shows a supramolecular 3D structure in the crystal; the structure is stabilized by hydrogen bonds between the layers of ammonium cations and the layers of ferrocene-1,1′-diyldiphosphinate anions. The more hydrophobic and sterically crowded ferrocene-1,1′-diylbis(phenylphosphinate) anion of compound 2 together with ammonium cations and solvate water molecules forms supramolecular 2D layers in the crystal.

  二铵基铁烯-1,1'-二基二（H-膦酸盐）（1）和二铵基铁烯-1,1'-二基双（苯基膦酸盐）（2）首次制备并进行了结构表征。化合物1在晶体中显示出超分子三维结构；该结构通过铵阳离子层与铁烯-1,1'-二基二膦酸盐阴离子层之间的氢键而得以稳定。化合物2中更具亲水性和空间拥挤的铁烯-1,1'-二基双（苯基膦酸盐）阴离子与铵阳离子和溶剂水分子共同形成晶体中的超分子二维层。
• Ferrocene-based <i>P</i>-chiral amidophosphinate: stereoselective synthesis and X-ray structural study
  作者：Ruslan P. Shekurov、Almaz A. Zagidullin、Mikhail N. Khrizanforov、Daut R. Islamov、Tatiana P. Gerasimova、Farida F. Akhmatkhanova、Vasily A. Miluykov

  DOI：10.1039/d2dt02930h

  日期：——

  amine with tetracoordinated phosphorus(V) chlorides. The structures of rac- and (R)-Ugi's amine ferrocenyl(phenyl)phosphinic acid N,N-diethylamide have been extensively studied experimentally (NMR, X-ray analysis, electrochemistry). The CV first peak refers to the oxidation of the amine fragment, which is clearly seen when (R)-Ugi's amine ferrocenyl(phenyl)phosphinic acid N,N-diethylamide reacts with

  外消旋和对映纯二茂铁基P-手性氨基次膦酸盐已通过外消旋-或 (R)-Ugi 胺的邻位锂化并进一步与氨基氯苯基次膦酸盐 Cl-P(O)(Ph)NEt 2反应，简单且立体选择性地合成。这是邻锂化 Ugi 胺与四配位氯化磷 ( V )发生不对称反应的第一个例子。rac - and ( R )-Ugi's amine ferrocenyl(phenyl)phosphinic acid N , N的结构-二乙胺已通过实验进行了广泛研究（NMR、X 射线分析、电化学）。CV 第一个峰是指胺片段的氧化，当 ( R )-Ugi 的胺二茂铁基(苯基)次膦酸N , N-二乙酰胺与无水酸反应时可以清楚地看到这一点。添加两当量的 CF 3 COOH 导致氮原子质子化，并观察到 ​​Fe( II ) 氧化为 Fe( III ) 的经典可逆波。
• FRAGMENTATION OF A PHENYLPHOSPHONAMIDIC ACID AS A NEW TECHNIQUE FOR THE GENERATION OF PHENYL DIOXOPHOSPHORANE
  作者：Gyöngyi Szakal Quin、Stefan Jankowski、Louis D. Quin

  DOI：10.1080/10426509608037956

  日期：1996.8.1

  N-(1-Adamantyl) phenylphosphonamidic acid (3), an easily prepared solid, on heating in toluene or 1,2-dichloroethane gave the crystalline adamantylamine salt of the anhydride PhP(O)(NHAd)-O-PPh(O)(OH). The mechanism is proposed to involve first the fragmentation of 3 to form phenyl dioxophosphorane, PhPO(2), which then acts as a phosphorylating agent to unreacted 3. This mechanism was supported by the observation of first-order kinetics for the consumption of 3. When the phosphonamidic acid was fragmented in the presence of an alcohol, the intermediate PhPO(2) was trapped as the monoalkyl phenylphosphonate. The OH groups on the surface of silica gel were also phosphonylated by PhPO(2). The acidic OH group of a phosphoric acid monoester (thymyl phosphate) was phosphonylated to give Thy-O-P(O)(OH)-O-PPh(O)(OH). It is concluded from this study that N-(1-adamantyl) phenylphosphonamidic acid is a useful precursor of phenyl dioxophosphorane, which can perform valuable phosphonylation operations.