1,8-bis(dimethylamino)naphthalene (hydrogen fluoride)

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-bis(dimethylamino)naphthalene (hydrogen fluoride)
• 英文别名: 1,8-bis(dimethylamino)naphthalene hydrogen fluoride；"Proton Sponge" hydrofluoride；PSHF；proton sponge hydrogen fluoride；1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine;hydrofluoride
• 化学式: C₁₄H₁₈N₂*FH
• 分子量: 234.317
• InChiKey: VOZAYSKSFCBUPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,8-bis(dimethylamino)naphthalene (hydrogen fluoride) 以 乙醚 为溶剂， 以96%的产率得到1,8-bis(dimethylamino)naphthalene tris(hydrogen fluoride)
  参考文献：
  名称：

  通过“质子海绵”-三乙胺三（氟化氢）体系促进的氯二嗪和氯吡啶的卤素交换进行选择性氟化

  摘要：

  “质子海绵”-三乙胺三（氟化氢）混合物提供了一种温和而有效的氟化试剂，可通过卤素交换将氟原子选择性地引入氯二嗪和氯硝基吡啶系列中。

  DOI：

  10.1016/s0040-4020(00)01060-7
• 作为产物：
  描述：

  1,8-双二甲氨基萘 在 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 90.0~95.0 ℃ 、2.0 kPa 条件下， 反应 1.5h， 以98%的产率得到1,8-bis(dimethylamino)naphthalene (hydrogen fluoride)
  参考文献：
  名称：

  通过“质子海绵”-三乙胺三（氟化氢）体系促进的氯二嗪和氯吡啶的卤素交换进行选择性氟化

  摘要：

  “质子海绵”-三乙胺三（氟化氢）混合物提供了一种温和而有效的氟化试剂，可通过卤素交换将氟原子选择性地引入氯二嗪和氯硝基吡啶系列中。

  DOI：

  10.1016/s0040-4020(00)01060-7
• 作为试剂：
  描述：

  2,4-二氯嘧啶 在 1,8-bis(dimethylamino)naphthalene (hydrogen fluoride) 作用下， 反应 48.0h， 以40%的产率得到2-氯-4-氟嘧啶
  参考文献：
  名称：

  通过“质子海绵”-三乙胺三（氟化氢）体系促进的氯二嗪和氯吡啶的卤素交换进行选择性氟化

  摘要：

  “质子海绵”-三乙胺三（氟化氢）混合物提供了一种温和而有效的氟化试剂，可通过卤素交换将氟原子选择性地引入氯二嗪和氯硝基吡啶系列中。

  DOI：

  10.1016/s0040-4020(00)01060-7

文献信息

• Fighting Obesity with a Sugar-Based Library: Discovery of Novel MCH-1R Antagonists by a New Computational–VAST Approach for Exploration of GPCR Binding Sites
  作者：Alexander Heifetz、Oliver Barker、Geraldine Verquin、Norbert Wimmer、Wim Meutermans、Sandeep Pal、Richard J. Law、Mark Whittaker

  DOI：10.1021/ci4000882

  日期：2013.5.24

  Obesity is an increasingly common disease. While antagonism of the melanin-concentrating hormone-1 receptor (MCH-1R) has been widely reported as a promising therapeutic avenue for obesity treatment, no MCH-1R antagonists have reached the market. Discovery and optimization of new chemical matter targeting MCH-1R is hindered by reduced HTS success rates and a lack of structural information about the

  肥胖是一种越来越常见的疾病。虽然已经广泛报道了黑色素浓缩激素-1受体（MCH-1R）的拮抗作用是肥胖治疗的一种有希望的治疗途径，但尚未有MCH-1R拮抗剂进入市场。降低HTS成功率和缺乏有关MCH-1R结合位点的结构信息，阻碍了针对MCH-1R的新化学物质的发现和优化。X射线晶体学和NMR是结构信息的主要实验来源，它们是膜蛋白的非常缓慢的过程，目前不适用于每种GPCR或GPCR-配体复合物。这种情况极大地限制了这些方法“实时”影响GPCR靶标的药物发现过程的能力，因此，迫切需要其他实用且具有成本效益的替代方法。我们在这里提出一种在概念上具有先驱性的方法，该方法将GPCR建模与VAST技术（稳定模板上的多功能组装）的多种糖基化合物的设计，合成和筛选相集成，以提供有关MCH-1R结合位点的结构见解。这种方法为针对GPCR靶标的基于结构的药物发现（SBDD）创建了一种经济高效的新途径。在我们的工
• Reactions involving fluoride ion. Part 37. ‘Proton Sponge’ hydrofluoride as a fluoride ion donor
  作者：Richard D. Chambers、Stewart R. Korn、Graham Sandford

  DOI：10.1016/0022-1139(93)03052-n

  日期：1994.10

  ‘Proton Sponge’ hydrofluoride has been prepared and is totally soluble in acetonitrile; this system has been used to generate carbanions from hexafluoropropene and to form carbon-fluorine bonds by reaction with both 2,4,6-trichloropyrimidine and benzoyl chloride.

  已经制备了“质子海绵”氢氟化物，它完全可溶于乙腈；该系统已被用来从六氟丙烯生成碳负离子，并通过与2,4,6-三氯嘧啶和苯甲酰氯的反应形成碳-氟键。
• A Versatile Synthetic Approach toward Diversity Libraries using Monosaccharide Scaffolds
  作者：Giang Le Thanh、Giovanni Abbenante、George Adamson、Bernd Becker、Chris Clark、Glenn Condie、Tania Falzun、Matthias Grathwohl、Praveer Gupta、Michael Hanson、Ngoc Huynh、Peter Katavic、Krystle Kuipers、Ann Lam、Ligong Liu、Maretta Mann、Jeff Mason、Declan McKeveney、Craig Muldoon、Andrew Pearson、Premraj Rajaratnam、Sarah Ryan、Gerry Tometzki、Geraldine Verquin、Jennifer Waanders、Michael West、Neil Wilcox、Norbert Wimmer、Annika Yau、Johannes Zuegg、Wim Meutermans

  DOI：10.1021/jo9021919

  日期：2010.1.1

  The pyranose scaffold is unique in its ability to position pharmacophore substituents in various ways in 3D space, and unique pharmacophore scanning libraries could be envisaged that focus on scanning topography rather than diversity in the type Of substituents. Approaches have been described that make use of amine and acid functionalities on the pyranose scaffolds to append substituents, and this has enabled the generation of libraries of significant structural diversity. Our general aim was to generate libraries of pyranose-based drug-like mimetics, where the substituents are held close to the scaffold, in order to obtain molecules with better defined positions for the pharmacophore substituents. Here we describe the development of a versatile synthetic route toward peptide mimetics build oil 2-amino pyranose scaffolds. The method allows introduction of a wide range of substituent types, it is regio- and stereospecific, and the later diversity steps are performed on solid phase. Further, the same process was applied oil glucose mid allose scaffolds, in the exemplified cases, and is likely adaptable to other pyranose building blocks. The methods developed in this work give access to molecules that position the three selected binding elements in various 3D orientations oil a pyranose scaffold and have been applied for the production of a systematically diverse library of several hundred monosaccharide-based mimetics.