6-氯四唑并[1,5-a]吡啶 | 242815-91-4

• 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
• 中文名称: 6-氯四唑并[1,5-a]吡啶
• 中文别名: 6-氯[1,5-A]吡啶并四氮唑
• 英文名称: 6-chlorotetrazolo[1,5-a]pyridine
• CAS: 242815-91-4
• 化学式: C₅H₃ClN₄
• 分子量: 154.559
• InChiKey: LNZZACOLEATCOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P310+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-氯四唑并[1,5-a]吡啶 以 三氟乙酸 为溶剂， 生成 2-azido-5-chloropyridine
  参考文献：
  名称：

  1H,13C and15N NMR and IR studies of halogen-substituted tetrazolo[1,5-a]pyridines

  摘要：

  The tetrazole-azide tautomerization of some halogen-substituted tetrazolo[1,5-a]pyridines was examined by IR spectroscopy at ambient temperature and by H-1,C-13 and N-15 NMR spectroscopy at various temperatures. The tetrazolopyridines can exhibit equilibrium between the azide and the tetrazole forms. For some of them slow exchange occurs on the NMR time-scale, such that it is possible to estimate equilibrium constants. The position and nature of the substituent in the pyridine ring result in stabilization or destabilization of the tetrazole form and exert a strong influence on the values found for the equilibrium constants. A saturation transfer experiment was carried out for 5-bromotetrazolo[1,5-a]pyridine and the rate constants were estimated. Moreover, based on the van't Hoff equation, the enthalpy Delta H degrees and entropy Delta S degrees for the tautomerization were calculated. Ab initio calculated energies and charge distribution are in good agreement with differences observed in the tetrazole-azide equilibrium constants. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199906)12:6<470::aid-poc151>3.0.co;2-u
• 作为产物：
  描述：

  2,5-二氯吡啶 在 盐酸 、 sodium azide 作用下， 以 乙醇 、 水 为溶剂， 以78 %的产率得到6-氯四唑并[1,5-a]吡啶
  参考文献：
  名称：

  通过自由基激活机制铁催化分子间 C-N 交叉偶联反应

  摘要：

  在铁催化条件下，使用四唑、芳香族和脂肪族叠氮化物与硼酸，发现了分子间 C-N 交叉偶联胺化的概念。胺化遵循前所未有的金属自由基活化机制，不同于传统的金属催化的 C-N 交叉偶联反应。该反应的范围已通过大量四唑、叠氮化物和硼酸的使用得到证明。此外，还展示了几种后期胺化反应和候选药物的简短合成，以供进一步的合成应用。总的来说，这种铁催化的 C-N 交叉偶联应该在药物化学、药物发现和制药工业中具有广泛的应用。

  DOI：

  10.1021/jacs.3c05627

文献信息

• Dual Reactivity of 1,2,3,4‐Tetrazole: Manganese‐Catalyzed Click Reaction and Denitrogenative Annulation
  作者：Hillol Khatua、Sandip Kumar Das、Satyajit Roy、Buddhadeb Chattopadhyay

  DOI：10.1002/anie.202009078

  日期：2021.1.4

  A general catalytic method using a Mn‐porphyrin‐based catalytic system is reported that enables two different reactions (click reaction and denitrogenative annulation) and affords two different classes of nitrogen heterocycles, 1,5‐disubstituted 1,2,3‐triazoles (with a pyridyl motif) and 1,2,4‐triazolo‐pyridines. Mechanistic investigations suggest that although the click reaction likely proceeds through

  据报道，使用基于锰卟啉的催化系统的一般催化方法可实现两种不同的反应（点击反应和脱氮环化反应），并提供两种不同类型的氮杂环，即1,5-二取代的1,2,3-三唑（具有吡啶基）和1,2,4-三唑并吡啶。机理研究表明，尽管点击反应可能是通过离子机理进行的，这与传统的点击反应不同，但脱氮环化反应可能是通过亲电子的茂金属中间体而不是金属金属中间体进行的。总体而言，此方法非常高效，与其他方法相比，具有许多优点。例如，2副产品产生气体。
• SNAr azidation of phenolic functions utilizing diphenyl phosphorazidate
  作者：Kotaro Ishihara、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tetlet.2019.151493

  日期：2020.2

  A useful method for the synthesis of aryl azides via SNAr reaction of phenol derivatives using diphenyl phosphorazidate (DPPA) as an azidation reagent was developed. Various phenol derivatives bearing electron-withdrawing groups were converted into the corresponding aryl azides in a single step. This method is easy to perform and enables the preparation of aryl azides without the use of explosive azide

  开发了一种有用的方法，该方法通过使用叠氮磷酸二苯酯（DPPA）作为叠氮化试剂通过苯酚衍生物的SNAr反应进行芳基叠氮化物的合成。带有吸电子基团的各种酚衍生物可在一个步骤中转化为相应的芳基叠氮化物。该方法易于实施，并且能够在不使用爆炸性叠氮化物源的情况下制备芳基叠氮化物。
• One-Step Conversion of Pyridine <i>N</i>-Oxides to Tetrazolo[1,5-<i>a</i>]pyridines
  作者：John M. Keith

  DOI：10.1021/jo061819j

  日期：2006.12.1

  Pyridine N-oxides were converted to tetrazolo[1,5-a]pyridines in good to excellent yield by heating in the presence sulfonyl or phosphoryl azides and pyridine in the absence of solvent. Various sulfonyl and phosphoryl azides were screened for reactivity under a standard set of conditions. Diphenyl phosphorazidate was the most convenient reagent and gave high yields. Reaction optimization, scope, and

  通过在磺酰基或磷酰基叠氮化物和吡啶存在下加热，在不存在溶剂的情况下加热，将吡啶N-氧化物以良好或优异的产率转化为四唑并[1,5- a ]吡啶。在一组标准条件下筛选各种磺酰基和磷酰基叠氮化物的反应性。叠氮磷酸二苯酯是最方便的试剂，收率很高。讨论了反应优化，范围和可伸缩性。
• Silver halide emulsion
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP0474047A1

  公开（公告）日：1992-03-11

  Disclosed is a silver halide emulsion, which comprises at least one methine dye represented by the general formula (I): wherein MET represents an atomic group having a methine dye structure; Q represents a divalent linking group containing at least one carbon, nitrogen, sulfur or oxygen atom; ℓ1 represents an integer 1 or 2; 12 represents an integer 0 or 1, ℓ3 represents an integer from 1 to 4; and Ar represents an aromatic polycyclic group formed of 8 or more atoms containing at least one nitrogen atom, with the proviso that said nitrogen atom is in a form such that tautomerism does not produce Also disclosed is a silver halide photographic material, which comprises on a support a silver halide photographic emulsion layer comprising silver halide grains containing iron ions in an amount of 10-7 to 10-3 mol per mol of silver halide and having a localized phase with an iron ion concentration of 10 times or more than that of the other portions, in a surface layer falling within 50% or less of the volume of the grain and at least one methine dye represented by general formula (I') and which exhibits a blue sensitivity difference of 0.1 or less between when it is developed after exposure in vacuo under 10-5 torr and when it is developed after exposure in air under 760 torr: wherein MET represents an atomic group having a methine dye structure; Q represents a divalent linking group containing at least one of a carbon, a nitrogen, a sulfur or an oxygen atom; Ar' represents an aromatic polycyclic group formed of 8 or more atoms; ℓ1 represents an integer 1 or 2; 12 represents an integer 0 or 1; and ℓ3 represents an integer from 1 to 4.

  本发明公开了一种卤化银乳液，它包含至少一种由通式（I）表示的甲基染料： 其中，MET 代表具有亚甲基染料结构的原子团；Q 代表至少含有一个碳原子、氮原子、硫原子或氧原子的二价连接基团；ℓ1 代表整数 1 或 2；12 代表整数 0 或 1，ℓ3 代表 1 至 4 的整数；Ar 代表由 8 个或更多含有至少一个氮原子的原子组成的芳香族多环基团，但上述氮原子的形态不会产生同分异构现象。 本发明还公开了一种卤化银感光材料，它包括在支撑体上的卤化银感光乳剂层，该层由卤化银颗粒组成，卤化银颗粒中含有铁离子，含量为每摩尔卤化银 10-7 至 10-3 摩尔，并且在颗粒体积的 50%或更小的表面层中，具有铁离子浓度为其他部分 10 倍或更高的局部相，以及至少一种由通式(I')表示的甲胺染料，该材料在显影时的蓝色感光度差为 0.在 10-5 托的真空中曝光后显影与在 760 托的空气中曝光后显影的蓝色灵敏度差异为 0.1 或更小： 其中，MET 代表具有亚甲基染料结构的原子团；Q 代表含有碳原子、氮原子、硫原子或氧原子中至少一个原子的二价连接基团；Ar' 代表由 8 个或更多原子组成的芳香族多环基团；ℓ1 代表 1 或 2 的整数；12 代表 0 或 1 的整数；ℓ3 代表 1 至 4 的整数。
• Silver halide photographic material
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP0647878A2

  公开（公告）日：1995-04-12

  Disclosed is a silver halide photographic material, which comprises on a support a silver halide photographic emulsion layer comprising silver halide grains containing iron ions in an amount of 10-7 to 10-3 mol per mol of silver halide and having a localized phase with an iron ion concentration of 10 times or more than that of the other portions, in a surface layer falling within 50% or less of the volume of the grain and at least one methine dye represented by general formula (I') and which exhibits a blue sensitivity difference of 0.1 or less between when it is developed after exposure in vacuo under 10-5 torr and when it is developed after exposure in air under 760 torr: wherein MET represents an atomic group having a methine dye structure; Q represents a divalent linking group containing at least one of a carbon, a nitrogen, a sulfur or an oxygen atom; Ar' represents an aromatic polycyclic group formed of 8 or more atoms; ℓ1 represents an integer 1 or 2; 12 represents an integer 0 or 1; and ℓ3 represents an integer from 1 to 4.

  本发明公开了一种卤化银感光材料，它包括在支撑体上的卤化银感光乳剂层，该层由每摩尔卤化银含有10-7至10-3摩尔量的铁离子的卤化银颗粒组成，在颗粒体积的50%或更小的表面层中，具有铁离子浓度为其他部分10倍或更高的局部相，以及至少一种由通式(I')表示的甲胺染料，在10-5托下的真空中曝光后与在760托下的空气中曝光后的蓝色感光度差为0.在 10-5 托的真空中曝光后显影与在 760 托的空气中曝光后显影的蓝色灵敏度差异为 0.1 或更小： 其中，MET 代表具有亚甲基染料结构的原子团；Q 代表含有碳原子、氮原子、硫原子或氧原子中至少一个原子的二价连接基团；Ar' 代表由 8 个或更多原子组成的芳香族多环基团；ℓ1 代表 1 或 2 的整数；12 代表 0 或 1 的整数；ℓ3 代表 1 至 4 的整数。