1H,1'H-1,1'-propanediyl-bis-pyridin-2-one | 56505-25-0

• 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: 1H,1'H-1,1'-propanediyl-bis-pyridin-2-one
• 英文别名: 1H,1'H-1,1'-Propandiyl-bis-pyridin-2-on；1,1'-(Propane-1,3-diyl)dipyridin-2(1H)-one；1-[3-(2-oxopyridin-1-yl)propyl]pyridin-2-one
• CAS: 56505-25-0
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: CSGGJEAFTZZHDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H,1'H-1,1'-propanediyl-bis-pyridin-2-one 在 乙醇 、 镍 作用下， 生成 1,1'-propanediyl-bis-piperidin-2-one
  参考文献：
  名称：

  Gautier; Renault, Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 421,426

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-bis(2-bromopyridinium)propane bromide 在 sodium hydroxide 作用下， 以 水 为溶剂， 以90%的产率得到1H,1'H-1,1'-propanediyl-bis-pyridin-2-one
  参考文献：
  名称：

  Reactions of 1,?-bis(2-bromopyridinium)alkanes with hydroxide ion in aqueous solutions

  摘要：

  The reaction of OH- ion with 1,omega-bis(2-bromopyridinium)alkanes, where the reaction centers are separated by a varying number of methylene groups, was investigated to model the increased velocity of OH- attack on premicellar aggregated N-alkylpyridinium compounds. 1,omega-Bis(2-bromopyridinium)alkanes (RPBr) [R = propane (I), butane (II), pentane (III), hexane (IV) and octane (V)] were synthesized and characterized by standard procedures. The kinetics of I-V with OH- ion fitted two consecutive first-order reactions. The intermediate products, 1-(2-pyridone)-omega-(2-bromopyridinium)alkane, and also the final products 1,omega-bis(2-pyridone)alkanes, were isolated. Deuterium isotope effects, activation parameters and salt effects on the reaction rates suggest that OH- attack is rate limiting and there is a through-space acceleration of the initial attack due to the proximity of the positive charges. These results place an upper limit of 20-fold for the electrostatic acceleration in OH- attack in premicellar aggregates. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199801)11:1<25::aid-poc962>3.0.co;2-e

文献信息

• Alberti, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1195,1208
  作者：Alberti

  DOI：——

  日期：——
• US3951940A
  申请人：——

  公开号：US3951940A

  公开（公告）日：1976-04-20
• [EN] PYRIDINONES USEFUL AS ANTIATHEROSCLEROTIC AGENTS
  申请人：THE UPJOHN COMPANY

  公开号：WO1991009848A1

  公开（公告）日：1991-07-11

  (EN) The present invention relates to novel compounds of formula (I), and a method of using these compounds in mammals as therapeutic agents for the prevention or treatment of atherosclerosis and related diseases. In the said formula, R1 includes substituted pyridinones, pyridinyloxy, benzoxazoles, and benzoxazolin-2-thiones; and cis-CH=CHCH2OC(O)O(C1-C4)alkyl, -(CH2)nCH(OH)CH2O-phenyl-CO2R3, and -(CH2)nC(=O)CH2O-phenyl-CO2R3.(FR) La présente invention concerne de nouveaux composés de la formule (I), ainsi qu'un procédé d'utilisation de ces composés chez les mammifères comme agents thérapeutiques pour la prévention ou le traitement de l'athérosclérose et des maladies associées. Dans ladite formule, R1 comprend les substances suivantes: pyridinones, pyridinyloxy, benzoxazoles et benzoxazolin-2-thiones substitués; et cis-CH=CHCH2OC(O)O(C1-C4)alkyle, -(CH2)nCH(OH)CH2O-phényle-CO2R3, et -(CH2)nC(=O)CH2O-phényle-CO2R3.