2-[4-[cyano-(6-diethoxyphosphorylpyridin-2-yl)methyl]phenyl]-2-(6-diethoxyphosphorylpyridin-2-yl)acetonitrile | 134881-94-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2-[4-[cyano-(6-diethoxyphosphorylpyridin-2-yl)methyl]phenyl]-2-(6-diethoxyphosphorylpyridin-2-yl)acetonitrile
• CAS: 134881-94-0
• 化学式: C₂₈H₃₂N₄O₆P₂
• 分子量: 582.533
• InChiKey: BBWYZRFBZRZYBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  144.42
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-[4-[cyano-(6-diethoxyphosphorylpyridin-2-yl)methyl]phenyl]-2-(6-diethoxyphosphorylpyridin-2-yl)acetonitrile 以 氘代二甲亚砜 、 二氯甲烷 、 氘代乙腈 为溶剂， 反应 84.0h， 生成 6,6'-<2,5-Cyclohexadiene-1,4-diylidenebis(cyanomethyl)>bis(2-pyridine)diphosphonic Acid (anti-isomer)
  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 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-[4-[cyano-(6-diethoxyphosphorylpyridin-2-yl)methyl]phenyl]-2-(6-diethoxyphosphorylpyridin-2-yl)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