4-benzyl-4-methylmorpholin-4-ium bromide

• 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: 4-benzyl-4-methylmorpholin-4-ium bromide
• 英文别名: 1-benzyl-1-methyl-morpholinium bromide；4-benzyl-4-methyl-morpholinium; bromide；4-Benzyl-4-methylmorpholin-4-ium;bromide
• 化学式: Br*C₁₂H₁₈NO
• 分子量: 272.185
• InChiKey: CDRKYUYWYACUPM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1,1'-Bi-2-naphthol 、 4-benzyl-4-methylmorpholin-4-ium bromide 以 氯仿 为溶剂， 以81%的产率得到1-benzyl-1-methylmorpholiniumbromide (R)-1,10-bi-2-naphthol
  参考文献：
  名称：

  [EN] METHOD OF SYNTHESIS
  [FR] PROCÉDÉ DE SYNTHÈSE

  摘要：

  The present invention provides a method of making an enantiomerically enriched tertiary or quaternary ammonium salt, and the use of a non-racemic chiral compound in the synthesis of an enantiomerically enriched tertiary or quaternary ammonium salt. The control of nitrogen-based chirality, achieved via the method of the invention, is useful where a specific tertiary or quaternary ammonium enantiomer is preferred over the other enantiomer, for example where a specific tertiary or quaternary ammonium enantiomer is more effective than the other enantiomer in treating a specific medical condition.

  公开号：

  WO2022101627A1
• 作为产物：
  描述：

  N-甲基吗啉 、 溴甲苯 以 乙醚 为溶剂， 反应 1.0h， 以62%的产率得到4-benzyl-4-methylmorpholin-4-ium bromide
  参考文献：
  名称：

  Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents

  摘要：

  Novel functionalized quaternary ammonium curcuminoids have been synthesized from piperazinyl curcuminoids and Baylis-Hillman reaction derived allyl bromides. These molecules are found to be highly water soluble with increased cytotoxicity compared to native curcumin against three cancer cell lines MIAPaCa-2, MDA-MB-231, and 4T1. Preliminary in vivo toxicity evaluation of a representative curcuminoid 5a in healthy mice indicates that this molecule is well tolerated based on normal body weight gains compared to control group. Furthermore, the efficacy of 5a has been tested in a pancreatic cancer xenograft model of MIAPaCa-2 and has been found to exhibit good tumor growth inhibition as a single agent and also in combination with clinical pancreatic cancer drug gemcitabine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.061

文献信息

• Degradation of Organic Cations under Alkaline Conditions
  作者：Wei You、Kristina M. Hugar、Ryan C. Selhorst、Megan Treichel、Cheyenne R. Peltier、Kevin J. T. Noonan、Geoffrey W. Coates

  DOI：10.1021/acs.joc.0c02051

  日期：2021.1.1

  degradation mechanisms of organic cations under basic conditions is extremely important for the development of durable alkaline energy conversion devices. Cations are key functional groups in alkaline anion exchange membranes (AAEMs), and AAEMs are critical components to conduct hydroxide anions in alkaline fuel cells. Previously, we have established a standard protocol to evaluate cation alkaline stability

  了解碱性条件下有机阳离子的降解机理对于开发耐用的碱性能量转换装置极为重要。阳离子是碱性阴离子交换膜（AAEM）中的关键官能团，而AAEM是在碱性燃料电池中传导氢氧根阴离子的关键组分。以前，我们已经建立了一个标准协议来评估KOH / CD 3中的阳离子碱稳定性80°C下的OH溶液。在这里，我们使用该协议比较26种模型化合物，包括苄基铵，四烷基铵，螺环铵，咪唑鎓，苯并咪唑鎓，三唑鎓，吡啶鎓，胍鎓和and阳离子。目的不仅是评估它们的降解速率，而且是确定它们的降解途径并导致具有改善的碱性稳定性的阳离子的发展。
• Verfahren zur Herstellung von Polycarbonaten
  申请人：BAYER AG

  公开号：EP0013904B1

  公开（公告）日：1983-03-09
• US4316980A
  申请人：——

  公开号：US4316980A

  公开（公告）日：1982-02-23
• Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents
  作者：Lucas N. Solano、Grady L. Nelson、Conor T. Ronayne、Erica A. Lueth、Melissa A. Foxley、Sravan K. Jonnalagadda、Shirisha Gurrapu、Venkatram R. Mereddy

  DOI：10.1016/j.bmcl.2015.10.061

  日期：2015.12

  Novel functionalized quaternary ammonium curcuminoids have been synthesized from piperazinyl curcuminoids and Baylis-Hillman reaction derived allyl bromides. These molecules are found to be highly water soluble with increased cytotoxicity compared to native curcumin against three cancer cell lines MIAPaCa-2, MDA-MB-231, and 4T1. Preliminary in vivo toxicity evaluation of a representative curcuminoid 5a in healthy mice indicates that this molecule is well tolerated based on normal body weight gains compared to control group. Furthermore, the efficacy of 5a has been tested in a pancreatic cancer xenograft model of MIAPaCa-2 and has been found to exhibit good tumor growth inhibition as a single agent and also in combination with clinical pancreatic cancer drug gemcitabine. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] METHOD OF SYNTHESIS<br/>[FR] PROCÉDÉ DE SYNTHÈSE
  申请人：[en]UNIVERSITY OF DURHAM

  公开号：WO2022101627A1

  公开（公告）日：2022-05-19

  The present invention provides a method of making an enantiomerically enriched tertiary or quaternary ammonium salt, and the use of a non-racemic chiral compound in the synthesis of an enantiomerically enriched tertiary or quaternary ammonium salt. The control of nitrogen-based chirality, achieved via the method of the invention, is useful where a specific tertiary or quaternary ammonium enantiomer is preferred over the other enantiomer, for example where a specific tertiary or quaternary ammonium enantiomer is more effective than the other enantiomer in treating a specific medical condition.