2-pivaloyl-6-chloropterin | 108473-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 2-pivaloyl-6-chloropterin
• 英文别名: Self-assembly of 2-pivaloylchloropterin；N-(6-chloro-4-oxo-3H-pteridin-2-yl)-2,2-dimethylpropanamide
• CAS: 108473-08-1
• 化学式: C₁₁H₁₂ClN₅O₂
• 分子量: 281.702
• InChiKey: SJQOVXNGMNTXKF-UHFFFAOYSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-pivaloyl-6-chloropterin 生成 tert-butyl 4-<<2-(pivaloylamino)-4(3H)-oxopteridin-6-yl>ethynyl>benzoate
  参考文献：
  名称：

  TAYLOR, EDWARD C.;RAY, PARTHA S., J. ORG. CHEM., 53,(1988) N 1, 35-38

  摘要：

  DOI：
• 作为产物：
  描述：

  6-chloropterin 生成 2-pivaloyl-6-chloropterin
  参考文献：
  名称：

  TAYLOR, EDWARD C.;RAY, PARTHA S., J. ORG. CHEM., 52,(1987) N 18, 3997-4000

  摘要：

  DOI：

文献信息

• One-Step Synthesis of Lumazine and Xanthine: First Co-Crystal of Lumazine and Perchloric Acid with a Unique Monohydrated Hydronium Ion (H5O2+) Mediated Supramolecular Assembly of the Lumazine Dimer
  作者：Shyamaprosad Goswami、Annada C. Maity、Hoong-Kun Fun

  DOI：10.1002/ejoc.200700271

  日期：2007.8

  A perchloric acid mediated one-step synthesis of lumazine derivatives from pterins and xanthine from guanine is reported. However, 2-pivaloylamino derivatives of pterins underwent simple hydrolysis of the pivaloylamino group generating free pterin compounds, but the 2-oxo derivatives, that is, the lumazine compounds, were not obtained. A novel supramolecular assembly is constructed by the unique hydrogen

  高氯酸介导的一步合成 lumazine 衍生物从蝶呤和黄嘌呤从鸟嘌呤合成。然而，蝶呤的 2-新戊酰氨基衍生物经过新戊酰氨基的简单水解，产生游离蝶呤化合物，但未获得 2-氧代衍生物，即 lumazine 化合物。通过 H5O2+ 的独特氢键桥接 lumazine 的两个氢键二聚体，与高氯酸水溶液形成共晶 21，构建了一种新型超分子组装体。相比之下，N2-pivaloyl-6-bromo-5-deazapterin 被简单地水解形成质子化的 deazapterin 22，它形成独特的六元环状氢键结构，导致生成聚合物超分子组装。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• A remarkable case of pterin specific oxidative coupling: unequivocal synthesis of 6,7-alkoxypterins and 1,4-dioxanopterin with ceric ammonium nitrate
  作者：Manas Kumar Das、Shyamaprosad Goswami、Ching Kheng Quah、Hoong-Kun Fun

  DOI：10.1016/j.tetlet.2016.06.031

  日期：2016.7

  single crystal X-ray structures of 6,7-dimethoxy and diethoxy-pterins) along with 1,4-dioxanopterin is reported along with a possible mechanism for their formation by treatment of pterins with ceric ammonium nitrate in methanol, ethanol, and ethylene glycol respectively. This unequivocal alkoxylation is unique only with pterin (and 5-deaza-pterin) and is unsuccessful with quinoxaline.

  已报道了一系列甲氧基和乙氧基取代的蝶呤（以6,7-二甲氧基和二乙氧基蝶呤的单晶X射线结构为特征）与1,4-二氧戊蝶呤的简便有效合成及其可能的机理通过分别在甲醇，乙醇和乙二醇中的硝酸铈铵处理蝶呤而形成。这种明确的烷氧基化仅在蝶呤（和5-脱氮蝶呤）中才是唯一的，而在喹喔啉中却不成功。
• Synthetic studies on the molybdenum cofactor: Total synthesis of pterindithiolenes by direct dithiolene formation from suitable pterin alkynes
  作者：Annada C. Maity、Manas Kumar Das、Sibaprasad Maity、Shyamaprosad Goswami

  DOI：10.1080/00397911.2018.1457697

  日期：2018.7.3

  ABSTRACT A novel, efficient total synthesis of a series of pterindithiolenes (15, 16, 17 and 18) [(5,6-dihydro-[1,4]dithiin or 6,7-dihydro-5H-[1,4]dithiepin systems respectively for six and seven membered dithiolenes] has been reported. The six membered quinoxaline thioketal 9 and seven membered quinoxaline dithiolene 11 have also been synthesized from quinoxaline acetylenic alcohol 5 and the corresponding

  摘要 一系列蝶二硫烯 (15, 16, 17 和 18) [(5,6-dihydro-[1,4] dithiin or 6,7-dihydro-5H-[1,4] dithiepin) 的新型高效全合成分别为六元和七元二硫醇的系统]已经报道。六元喹喔啉硫缩酮 9 和七元喹喔啉二硫醇 11 也分别由喹喔啉炔醇 5 和相应的炔酮 10 合成。五元蝶呤硫缩酮的合成 12还报道了通过与 NBS 反应将 13 和 13 以及 13 转化为二硫烯 14。
• Solvent-Dependent Pyranopterin Cyclization in Molybdenum Cofactor Model Complexes
  作者：Benjamin R. Williams、Douglas Gisewhite、Anna Kalinsky、Alisha Esmail、Sharon J. Nieter Burgmayer

  DOI：10.1021/acs.inorgchem.5b00532

  日期：2015.9.8

  Moco. Therefore, understanding the interconversion between the tricyclic and bicyclic forms, a type of ring–chain tautomerism, is an important aspect of study to understand its role in catalysis. In this study, equilibrium constants (Keq) as well as enthalpy, entropy, and free energy values are obtained for pyran ring tautomerism exhibited by two Moco model complexes, namely, (Et4N)[Tp*Mo(O)(S2BMOPP)]

  在几种细菌钼酶的蛋白质晶体结构中观察到，在单核Mo酶的辅因子（Moco）中协调钼（Mo）的保守的蝶呤二硫辛烯配体可以以三环吡喃蝶呤二硫辛烯形式存在，也可以以双环蝶呤-二硫辛烯形式存在。据推测，通过吡喃分裂和环化作用，三环和双环形式之间的相互转化在Moco的催化机理中起作用。因此，了解三环形式和双环形式（一种环链互变异构）之间的相互转化是了解其在催化中的作用的重要研究内容。在这项研究中，平衡常数（K eq）以及两个Moco模型配合物（Et 4 N）[Tp * Mo（O）（S 2 BMOPP）]（1）和（ Et 4 N）[Tp * Mo（O）（S 2 PEOPP）]（2），作为溶剂依赖性平衡过程。从七种氘代溶剂中的1 H NMR数据获得的K eq值显示出溶剂极性和互变异构体形式之间的相关性，其中极性参数较高的溶剂倾向于吡喃形式。
• Synthetic studies on the molybedenum cofactor. An efficient total synthesis of (±)-dephospho Form A
  作者：Edward C. Taylor、Shyamaprosad Goswami

  DOI：10.1016/0040-4039(91)80106-g

  日期：1991.12

  (Dephospho) Form A (4b), obtained by oxidative degradation of the molybdenum cofactor, has been efficiently synthesized in racemic form for the first time. This material, as well as its protected derivative 11, are now conveniently available as intermediates for a projected synthesis of the natural cofactor.

  通过钼辅助因子的氧化降解获得的（脱磷）晶型A（4b）首次以外消旋形式有效合成。现在，该材料及其受保护的衍生物11可以方便地用作天然辅因子的预计合成的中间体。