N,N'-二苯基磷酰氯二胺 | 5625-99-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酰卤
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N'-二苯基磷酰氯二胺
• 英文名称: N,N'-diphenylphosphorodiamidic chloride
• 英文别名: Phosphorodiamidic chloride, N,N'-diphenyl-；N-[anilino(chloro)phosphoryl]aniline
• CAS: 5625-99-0
• 化学式: C₁₂H₁₂ClN₂OP
• 分子量: 266.667
• InChiKey: SEJRCEHFBBPZIV-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  382.5±25.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-二苯基磷酰氯二胺 在 吡啶 、 四氮唑 、 triisopropylbenzenesulfonyl chloride 作用下， 以 二氯甲烷 为溶剂， 反应 120.5h， 生成 8-bromo-N¹-[5''-O-[bis-(phenylthio)phosphoryl]-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine
  参考文献：
  名称：

  Syntheses and Calcium-Mobilizing Evaluations of N-Glycosyl-Substituted Stable Mimics of Cyclic ADP-Ribose

  摘要：

  Cyclic ADP-ribose (cADPR) is not only a potent endogenous calcium modulator but also a second messenger. However, studies on the mechanism of cADPR action were limited due to its instability and lack of available structural modifications in the N-1-glyosyl unit of cADPR. In the present work, a series of N-1-glycosyl mimics with different configurational glycosyls or an ether strand were designed and synthesized mimicking the furanose ring. S(N)2 substitutions were carried out between the protected inosine and glycosyl triflates to form the N-1-glycosylinosine derivatives, accompanied with some O-6-glyeosyl-substituted as side products. The intramolecular cyclization was followed the strategy described by Matsuda et al. It was found that the 8-unsubstituted substrate could also be used to construct the intramolecular cyclic pyrophosphate. The activities of NI-glycosyl-substituted cADPR mimics were evaluated by induced Ca2+ release in rat brain microsomes and HeLa cells. It was found that the configuration of the N-1-glycosyl moiety in cADPR is not a critical structural factor for retaining the activity of mobilizing Ca2+ release. More interestingly, the N-1-acyclic analogue 6 exhibited strong activity by inducing Ca2+ release in both rat brain microsomes and HeLa cells. It constitutes a useful tool for further studies.

  DOI：

  10.1021/jm010530l
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 作用下， 生成 N,N'-二苯基磷酰氯二胺
  参考文献：
  名称：

  Autenrieth; Rudolph, Chemische Berichte, 1900, vol. 33, p. 2110

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-吡啶甲酸 在 N-乙基哌啶 、 N,N'-二苯基磷酰氯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 吡啶-2-甲酸酐
  参考文献：
  名称：

  A New Reagent for Activating Carboxy Groups; Preparation and Reactions of PhenylN-Phenylphosphoramidochloridate

  摘要：

  DOI：

  10.1055/s-1982-29783

文献信息

• Phosphorus-Nitrogen Compounds XVIII: Hydrazides and Thiosemicarbazides
  作者：L.A. Cates、T.L. Lemke

  DOI：10.1002/jps.2600631114

  日期：1974.11

  Abstract: Phenylphosphono(thio)dihydrazides and phosphorylated thiosemicarbazides were synthesized for anticancer testing, and some of these agents displayed chelation properties. Reactions involving methylhydrazine resulted in substitution of N 1 -protons. A study of diphenylphosphoro and phosphoramidomethylhydrazides also indicated that the N 1 -phosphorylated isomers are predominately formed.

  摘要：合成了苯基膦酰基（硫代）二酰肼和磷酸化的硫代氨基甲酰肼用于抗癌试验，其中一些试剂表现出螯合性能。涉及甲基肼的反应导致N 1-质子的取代。对二苯基磷和磷酰氨基甲基酰肼的研究还表明，主要形成了N 1-磷酸化的异构体。
• New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions
  作者：Helge Klare、Jörg M Neudörfl、Bernd Goldfuss

  DOI：10.3762/bjoc.10.18

  日期：——

  catalysts based on open-chain P(V)-amides of BINOL and chinchona alkaloids as well as three catalysts based on rigid cis-P(V)-cyclodiphosphazane amides of N (1),N (1)-dimethylcyclohexane-1,2-diamine have been developed. Employed in the asymmetric Michael addition of 2-hydroxynaphthoquinone to beta-nitrostyrene, the open-chain 9-epi-aminochinchona-based phosphorus amides show a high catalytic activity

  十种基于 BINOL 和金鸡纳生物碱的开链 P(V)-酰胺的新型氢键催化剂以及三种基于 N (1),N (1)- 刚性顺式-P(V)-环二磷氮烷酰胺的催化剂已开发出二甲基环己烷-1,2-二胺。在 2-羟基萘醌与 β-硝基苯乙烯的不对称迈克尔加成中，基于开链 9-epi-aminochinchona 的磷酰胺表现出高催化活性，几乎定量的产率高达 98%，对映体过量高达 51% . 环二磷氮烷催化剂表现出同样的高活性，并改善了高达 75% 的对映体过量，从而代表了环二磷氮烷在对映选择性有机催化中的首次成功应用。DFT 计算表明，与脲基催化剂相比，环二磷氮烷 P(V)-酰胺具有较高的氢键强度。对顺式环二磷氮烷 14a 的对映测定步骤的实验结果和计算表明，催化剂对硝基苯乙烯底物有很强的双齿 H 键活化。
• Chiral (thio)phosphorodiamides as excellent hydrogen bond donor catalysts in the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefins
  作者：Ronghua Wu、Xufang Chang、Aidang Lu、Youming Wang、Guiping Wu、Haibin Song、Zhenghong Zhou、Chuchi Tang

  DOI：10.1039/c1cc10797f

  日期：——

  A novel type of bidentate hydrogen bond donor catalysts based on (thio)phosphorodiamides catalophore has been developed for the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefins, affording the corresponding adducts in high yields with excellent level of enantioselectivities (97- >99% ee).

  已经开发出了一种新型的基于（硫代）磷二酰胺基阴极的双齿氢键供体催化剂，用于将2-羟基-1,4-萘并醌不对称地迈克尔加成到硝基烯烃中，从而以高收率提供相应的加合物，同时具有出色的对映选择性（ 97-> 99％ee）。
• Synthesis of a novel N-1 carbocyclic, N-9 butyl analogue of cyclic ADP ribose (cADPR)
  作者：Aldo Galeone、Luciano Mayol、Giorgia Oliviero、Gennaro Piccialli、Michela Varra

  DOI：10.1016/s0040-4020(01)01162-0

  日期：2002.1

  A new analogue 1 of cADPR was prepared through a synthetic pathway starting from 6-chloropurine 2 which underwent two sequential alkylations at N-9 and N-1, with formation of the intermediate 8. The successive bis-phosphorylation of hydroxyalkyl functions, followed by deprotection and reprotection steps, afforded the derivative 13, the substrate for the cyclization reaction. This was carried out according

  通过从6-氯嘌呤2开始的合成途径制备了cADPR的新类似物1，后者在N-9和N-1经历了两个连续的烷基化，形成了中间体8。羟基烷基官能团的连续双磷酸化，然后进行脱保护和再保护步骤，得到衍生物13，其为环化反应的底物。这是根据松田程序进行的，并导致分子内焦磷酸盐键的形成，从而得到14。在碱性条件下最终的14脱保护，以高收率得到目标化合物1。
• Synthesis of a New N1-Pentyl Analogue of Cyclic Inosine Diphosphate Ribose (cIDPR) as a Stable Potential Mimic of Cyclic ADP Ribose (cADPR)
  作者：Aldo Galeone、Luciano Mayol、Giorgia Oliviero、Gennaro Piccialli、Michela Varra

  DOI：10.1002/1099-0690(200212)2002:24<4234::aid-ejoc4234>3.0.co;2-8

  日期：2002.12

  7 of cADPR (1), a cyclic nucleotide bis(phosphate) involved in Ca2+ metabolism, was prepared starting from 2′,3′-isopropylideneinosine (8) which was alkylated at N-1, leading to the intermediate 11. Bis(phosphorylation) of 11 through two alternative procedures, followed by phosphate deprotection steps, afforded derivatives 15 and 16, the substrates for the intramolecular pyrophosphate bond formation

  cADPR (1) 的新类似物 7 是一种参与 Ca2+ 代谢的环核苷酸双（磷酸酯），从 2',3'-异亚丙基肌苷 (8) 开始制备，其在 N-1 处被烷基化，产生中间体 11。通过两个替代程序对 11 进行双（磷酸化），然后进行磷酸脱保护步骤，得到衍生物 15 和 16，它们是分子内焦磷酸键形成的底物。15 和 16 均以高产率转化为衍生物 17，最终脱保护得到目标化合物 7。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)