Diewthyl (6-Chloro-2-pyridyl)phosphonic Acid | 134882-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Diewthyl (6-Chloro-2-pyridyl)phosphonic Acid
• 英文别名: diethyl (6-chloropyridin-2-yl)phosphonate；Phosphonic acid, (6-chloro-2-pyridinyl)-, diethyl ester；2-chloro-6-diethoxyphosphorylpyridine
• CAS: 134882-01-2
• 化学式: C₉H₁₃ClNO₃P
• 分子量: 249.634
• InChiKey: QHNKPLMJZSLOFE-UHFFFAOYSA-N

物化性质

• 沸点：
  339.9±27.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diewthyl (6-Chloro-2-pyridyl)phosphonic Acid 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 84.0h， 生成 2-[6-bis(trimethylsilyloxy)phosphorylpyridin-2-yl]-2-[4-[[6-bis(trimethylsilyloxy)phosphorylpyridin-2-yl]-cyanomethyl]phenyl]acetonitrile
  参考文献：
  名称：

  Pyridyl dicyanoquinodimethane acceptors for electroactive solids

  摘要：

  A new synthetic strategy for dicyanoquinodimethane electron acceptors is presented and used to synthesize six such compounds for the first time. The general sequence is substitution of alpha,alpha'-dicyanoxylene alpha anions with electrophiles followed by oxidative dehydrogenation. Unlike most previous examples, these quinodimethanes (QDs) are alpha substituted, rather than ring substituted; thus, the substituents increase the aspect ratio of the QDs and extend the pi-systems. All contain at least one pyridyl substituent at an alpha-position, and the set includes polar, cationic, and phosphonic acid derivatives. The particular compounds were chosen for incorporation into specific types of potentially electroactive solids, although, in principle, the syntheses could accommodate a wide variety of other functional groups. The neutral QD compounds display two reversible reductions, while the cations show single, partially reversible electrochemical transitions. Syn-anti isomerism was noted for several of the QDs, and proton NMR assignments obtained by 2D COSY methods are reported.

  DOI：

  10.1021/jo00018a021
• 作为产物：
  描述：

  2-氯吡啶-N-氧化物 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 Diewthyl (6-Chloro-2-pyridyl)phosphonic Acid
  参考文献：
  名称：

  Pyridyl dicyanoquinodimethane acceptors for electroactive solids

  摘要：

  A new synthetic strategy for dicyanoquinodimethane electron acceptors is presented and used to synthesize six such compounds for the first time. The general sequence is substitution of alpha,alpha'-dicyanoxylene alpha anions with electrophiles followed by oxidative dehydrogenation. Unlike most previous examples, these quinodimethanes (QDs) are alpha substituted, rather than ring substituted; thus, the substituents increase the aspect ratio of the QDs and extend the pi-systems. All contain at least one pyridyl substituent at an alpha-position, and the set includes polar, cationic, and phosphonic acid derivatives. The particular compounds were chosen for incorporation into specific types of potentially electroactive solids, although, in principle, the syntheses could accommodate a wide variety of other functional groups. The neutral QD compounds display two reversible reductions, while the cations show single, partially reversible electrochemical transitions. Syn-anti isomerism was noted for several of the QDs, and proton NMR assignments obtained by 2D COSY methods are reported.

  DOI：

  10.1021/jo00018a021

文献信息

• Two cobalt monophosphonates: Syntheses, structures and magnetic properties
  作者：Yun-Sheng Ma、Li-Qin Zha、Wang-Shui Cai、Xiao-Yan Tang、Rong-Xin Yuan

  DOI：10.1016/j.ica.2013.04.035

  日期：2013.9

  in which Co 2 O 2 } dimers are connected through the corner-sharing of CoO 5 N} octahedra and PO 3 C} tetrahedra, forming an inorganic double-layer. Introduction of a second ligand (1,4-bis(imidazol-1-ylmethyl)benzene, L) in the reaction system, compound [Co(hppa)(L) 0.5 (H 2 O)]·H 2 O ( 3) was obtained. In this structure, Co 2+ ions are bridged by O–P–O bridges into an inorganic layer and the

  将6-氯-2-吡啶膦酸二乙酯在HCl溶液中水解，得到6-羟基-2-吡啶膦酸（H 2 hppa 1）。在结构中，广泛的氢键相互作用将膦酸分子连接成二维网络。H 2 hppa与乙酸钴在水热条件下的反应产生了新的膦酸钴Co（hppa）（H 2 O）（2）。化合物2显示了一种层结构，其中Co 2 O 2}二聚体通过CoO 5 N}八面体和PO 3 C}四面体的角共享而连接，从而形成无机双层。在反应体系中引入第二种配体（1,4-双（咪唑-1-基甲基）苯，L），化合物[Co（hppa）（L）0.5（H 2 O）]·H 2 O（3）获得了。在这种结构中，Co 2+离子通过O–P–O桥被桥接成一个无机层，并且这些层被1撑起。4-双（咪唑-1-基甲基）苯。磁性研究表明Co 2 O 2}单元中的Co 2+离子之间存在弱的铁磁耦合2。对于化合物3，O-P-O桥介导的反铁磁相互作用非常弱。
• Pyridyl dicyanoquinodimethane acceptors for electroactive solids
  作者：H. E. Katz、M. L. Schilling

  DOI：10.1021/jo00018a021

  日期：1991.8

  A new synthetic strategy for dicyanoquinodimethane electron acceptors is presented and used to synthesize six such compounds for the first time. The general sequence is substitution of alpha,alpha'-dicyanoxylene alpha anions with electrophiles followed by oxidative dehydrogenation. Unlike most previous examples, these quinodimethanes (QDs) are alpha substituted, rather than ring substituted; thus, the substituents increase the aspect ratio of the QDs and extend the pi-systems. All contain at least one pyridyl substituent at an alpha-position, and the set includes polar, cationic, and phosphonic acid derivatives. The particular compounds were chosen for incorporation into specific types of potentially electroactive solids, although, in principle, the syntheses could accommodate a wide variety of other functional groups. The neutral QD compounds display two reversible reductions, while the cations show single, partially reversible electrochemical transitions. Syn-anti isomerism was noted for several of the QDs, and proton NMR assignments obtained by 2D COSY methods are reported.