(1Z)-3-methoxy-N-pyridin-1-ium-1-ylbenzenecarboximidate | 81460-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1Z)-3-methoxy-N-pyridin-1-ium-1-ylbenzenecarboximidate
• CAS: 81460-45-9
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: RVRWCXWGOKWKDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (1Z)-3-methoxy-N-pyridin-1-ium-1-ylbenzenecarboximidate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以97.8%的产率得到N-(3,6-dihydro-2H-pyridin-1-yl)-3-methoxybenzamide
  参考文献：
  名称：

  Synthesis of N-[[(substituted-phenyl)carbonyl]amino]-1,2,3,6-tetrahydropyridines with analgesic and hyperglycemic activity

  摘要：

  A group of N-[(phenylcarbonyl)amino]1-2,3,6-tetrahydropyridines, 5, were synthesized to determine the effect that changes in aromatic substitution on the phenyl ring have on analgesic, hyperglycemic, and antiinflammatory activities. All of the N-[(phenylcarbonyl)amino]-1,2,3,6-tetrahydropyridines 5 exhibited potent analgesic activity, relative to morphine, irrespective of the position and physicochemical properties of the aromatic substituent. Pretreatment with naloxone did not alter the analgesic activity of the 4-fluorophenyl derivative 5P. N-[[(2-Fluorophenyl)-carbonyl]amino]-1,2,3,6-tetrahydropyridine (5n) was one of the most active hyperglycemic agents, elevating blood glucose 213 and 127% at 2 and 4 h after a 100 mg/kg po dose. Incorporation of aromatic substituents into the 3 and 4 positions of 1 abolished antiinflammatory activity.

  DOI：

  10.1021/jm00348a021
• 作为产物：
  描述：

  1-氨基吡啶碘 、 间甲氧基苯甲酰氯 在 sodium hydroxide 作用下， 反应 24.0h， 以94.6%的产率得到(1Z)-3-methoxy-N-pyridin-1-ium-1-ylbenzenecarboximidate
  参考文献：
  名称：

  Synthesis of N-[[(substituted-phenyl)carbonyl]amino]-1,2,3,6-tetrahydropyridines with analgesic and hyperglycemic activity

  摘要：

  A group of N-[(phenylcarbonyl)amino]1-2,3,6-tetrahydropyridines, 5, were synthesized to determine the effect that changes in aromatic substitution on the phenyl ring have on analgesic, hyperglycemic, and antiinflammatory activities. All of the N-[(phenylcarbonyl)amino]-1,2,3,6-tetrahydropyridines 5 exhibited potent analgesic activity, relative to morphine, irrespective of the position and physicochemical properties of the aromatic substituent. Pretreatment with naloxone did not alter the analgesic activity of the 4-fluorophenyl derivative 5P. N-[[(2-Fluorophenyl)-carbonyl]amino]-1,2,3,6-tetrahydropyridine (5n) was one of the most active hyperglycemic agents, elevating blood glucose 213 and 127% at 2 and 4 h after a 100 mg/kg po dose. Incorporation of aromatic substituents into the 3 and 4 positions of 1 abolished antiinflammatory activity.

  DOI：

  10.1021/jm00348a021

文献信息

• Rh( <scp>III</scp> )‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides
  作者：Zhenzhen Dong、Pengfei Li、Xingwei Li、Bingxian Liu

  DOI：10.1002/cjoc.202100203

  日期：2021.9

  Divergent synthesis of useful skeletons has been realized via rhodium(III)-catalyzed C—H activation of iminopyridinium ylides and coupling with various unsaturated coupling reagents. Isocoumarins and isoquinolones were obtained via cleavage of the C—N or N—N bond in the ylidic directing group, while fluorinated alkenes were delivered with the directing group intact. The reactions occurred with wide

  通过铑（III）催化的亚氨基吡啶鎓叶立德的CH活化并与各种不饱和偶联剂偶联，已经实现了有用骨架的发散合成。异香豆素和异喹诺酮获得经由所述C-N或N-N键的ylidic导向基团中的裂解，而氟化烯烃用的导向基团完整递送。该反应在氧化还原中性和耐空气条件下以广泛的底物范围和良好的效率发生。代表性产品表现出固态荧光特性和对人类癌细胞的抑制生物活性。
• Rh(III)-Catalyzed C–H Diamidation and Diamidation/Intramolecular Cyclization of <i>N</i>-Iminopyridinium Ylides with Dioxazolones
  作者：Xiang Li、Qing Zhao、Yang Shen、Ran Ma

  DOI：10.1021/acs.joc.1c03042

  日期：2022.3.4

  A highly efficient Rh(III)-catalyzed C–H diamidation and diamidation/intramolecular cyclization of N-iminopyridinium ylides with dioxazolones has been developed, providing diamidated products and benzoxazinone products in good to excellent yields. Notably, the tunable selectivity of this reaction can be controlled by simply switching the solvent and the temperature. This reaction features operational

  已开发出高效的 Rh(III) 催化的 C-H 二酰胺化和二酰胺化/分子内环化N-亚氨基吡啶鎓叶立德与二恶唑酮，以良好至优异的产率提供二酰胺化产物和苯并恶嗪酮产物。值得注意的是，该反应的可调选择性可以通过简单地切换溶剂和温度来控制。该反应具有操作简单、底物范围广、官能团耐受性好的特点。
• Ru(<scp>ii</scp>)-Catalyzed C–H bond activation/annulation of <i>N</i>-iminopyridinium ylides with sulfoxonium ylides
  作者：Xiang Li、Danlu Li、Xiaofei Zhang

  DOI：10.1039/d1ob02427b

  日期：——

  A Ru(II)-catalyzed C–H bond activation/annulation of N-iminopyridinium ylides with sulfoxonium ylides has been developed for the synthesis of diverse functionalized isocoumarin derivatives. This method features broad substrate scope, high functional group tolerance, simple operation and silver salt-free conditions. Furthermore, the synthetic utility of this method is demonstrated by the alkenylation

  已经开发了一种 Ru( II ) 催化的N-亚氨基吡啶叶立德与锍叶立德的 C-H 键活化/环化，用于合成各种官能化的异香豆素衍生物。该方法具有底物范围广、官能团耐受性高、操作简单、无银盐条件等特点。此外，该方法的合成效用通过产物的烯基化和生物活性 thunberginol A 的有效合成得到证明。
• 一种N-亚氨基吡啶叶立德双酰胺化合物的合成方法
  申请人：陕西科技大学

  公开号：CN113801059A

  公开（公告）日：2021-12-17

  本发明公开了一种N‑亚氨基吡啶叶立德双酰胺化合物的合成方法，向溶剂中加入N‑亚氨基吡啶叶立德和3‑苯基‑1,4,2‑二氧唑‑5‑酮，以及催化剂和碱，反应完成后进行分离提纯即得到N‑亚氨基吡啶叶立德双酰胺化合物。本发明的合成方法简洁高效，以在空气中稳定且易得的N‑亚氨基吡啶叶立德和3‑苯基‑1,4,2‑二氧唑‑5‑酮为反应原料，在溶剂的存在下，加入催化剂和碱，在温和的反应条件下高效合成N‑亚氨基吡啶叶立德双酰胺化合物。
• YEUNG, J. M.;CORLETO, L. A.;KNAUS, E. E., J. MED. CHEM., 1982, 25, N 6, 720-723
  作者：YEUNG, J. M.、CORLETO, L. A.、KNAUS, E. E.

  DOI：——

  日期：——