(E)-<β-(methoxycarbonyl)vinyl>iminophosphorane | 147151-45-9

• 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: (E)-<β-(methoxycarbonyl)vinyl>iminophosphorane
• 英文别名: (E)-[β-(methoxycarbonyl)vinyl]iminophosphorane；methyl (E)-3-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate；methyl (E)-3-[(triphenyl-λ5-phosphanylidene)amino]prop-2-enoate
• CAS: 147151-45-9
• 化学式: C₂₂H₂₀NO₂P
• 分子量: 361.38
• InChiKey: DQVYVNTVSNKDNG-ISLYRVAYSA-N

物化性质

• 沸点：
  498.5±47.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-cyclododec-2-enone 、 (E)-<β-(methoxycarbonyl)vinyl>iminophosphorane 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 48.0h， 以31%的产率得到5-(methoxycarbonyl)<9>(2,4)pyridinophane
  参考文献：
  名称：

  Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)

  摘要：

  [n](2,4)Pyridinophane derivatives 5-8 having an ester or an amide group at the 5-position were synthesized by aza-Wittig reactions between beta-substituted vinyliminophosphoranes and cyclic alpha,beta-unsaturated ketones. [beta-(Methoxycarbonyl)vinyl]- (1), [beta-(N,N-tetramethylenecarbamoyl)vinyl]-(2), [beta-(N-benzylcarbamoyl)vinyl]-(3), and (beta-carbamoylvinyl)iminophosphorane (4) were synthesized from the corresponding vinyl azides and triphenylphosphine. The heptamethylene chains of 5-(methoxycarbonyl)[7](2,4)pyridinophane (5),5-(N,N-tetramethylenecarbamoyl)[7](2,4)pyridinophane (6), and 5-(N-benzylcarbamoyl)[7](2,4)pyridinophane (7) flipped with AG(double dagger) = 11.2 (T(c) = 10.3-degrees-C), 10.8 (T(c) = 0.2-degrees-C), and 10.5 kcal/mol (T(c) = -5.2-degrees-C), respectively. At lower temperatures, the three conformations of the heptamethylene bridge were frozen. Methylpyridinium iodides 10 (n = 7, 6, and 5) derived from 6 were reduced more easily [E1/2* (half height potential) = -1.65 V (n = 7); -1.63 V (n = 6); -1.29 V vs Ag/AgCl (n = 5)] than the reference compound, 2,4-diethyl-5-(N,N-tetramethylenecarbamoyl)pyridinium ion (11) [E1/2* = -1.82 V vs Ag/AgCl]. The reduced species dimerized quickly.

  DOI：

  10.1021/jo00060a018
• 作为产物：
  描述：

  (E)-β-(methoxycarbonyl)vinyl azide 、 三苯基膦 以 乙醚 为溶剂， 以80%的产率得到(E)-<β-(methoxycarbonyl)vinyl>iminophosphorane
  参考文献：
  名称：

  Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)

  摘要：

  [n](2,4)Pyridinophane derivatives 5-8 having an ester or an amide group at the 5-position were synthesized by aza-Wittig reactions between beta-substituted vinyliminophosphoranes and cyclic alpha,beta-unsaturated ketones. [beta-(Methoxycarbonyl)vinyl]- (1), [beta-(N,N-tetramethylenecarbamoyl)vinyl]-(2), [beta-(N-benzylcarbamoyl)vinyl]-(3), and (beta-carbamoylvinyl)iminophosphorane (4) were synthesized from the corresponding vinyl azides and triphenylphosphine. The heptamethylene chains of 5-(methoxycarbonyl)[7](2,4)pyridinophane (5),5-(N,N-tetramethylenecarbamoyl)[7](2,4)pyridinophane (6), and 5-(N-benzylcarbamoyl)[7](2,4)pyridinophane (7) flipped with AG(double dagger) = 11.2 (T(c) = 10.3-degrees-C), 10.8 (T(c) = 0.2-degrees-C), and 10.5 kcal/mol (T(c) = -5.2-degrees-C), respectively. At lower temperatures, the three conformations of the heptamethylene bridge were frozen. Methylpyridinium iodides 10 (n = 7, 6, and 5) derived from 6 were reduced more easily [E1/2* (half height potential) = -1.65 V (n = 7); -1.63 V (n = 6); -1.29 V vs Ag/AgCl (n = 5)] than the reference compound, 2,4-diethyl-5-(N,N-tetramethylenecarbamoyl)pyridinium ion (11) [E1/2* = -1.82 V vs Ag/AgCl]. The reduced species dimerized quickly.

  DOI：

  10.1021/jo00060a018

文献信息

• [EN] POTENT AND SELECTIVE INHIBITORS OF THE CALCIUM-ACTIVATED POTASSIUM CHANNEL, KCa3.1, FOR USE AS PLATFORM THERAPEUTICS<br/>[FR] INHIBITEURS PUISSANTS ET SÉLECTIFS DE CANAUX POTASSIQUES ACTIVÉS PAR LE CALCIUM KCA3.1, DESTINÉS À ÊTRE UTILISÉS COMME PLATE-FORMES THÉRAPEUTIQUES
  申请人：UNIV NANYANG TECH

  公开号：WO2022115043A1

  公开（公告）日：2022-06-02

  Provided is the use of compounds of Formula I, as well as certain specific compounds, or a pharmaceutically acceptable salt, solvate or derivative thereof, in the preparation of a medicament to treat or prevent a disease condition that is associated with increased KCa3.1 or altered activity, such as stroke.

  本发明涉及使用I式化合物，以及某些特定的化合物，或其药学上可接受的盐、溶剂或衍生物，在制备用于治疗或预防与增加KCa3.1或改变其活性相关的疾病状态（例如中风）的药物中的用途。