3,4,5-trideuteriopyridine | 71150-39-5

• 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
• 英文名称: 3,4,5-trideuteriopyridine
• CAS: 71150-39-5
• 化学式: C₅H₅N
• 分子量: 82.0776
• InChiKey: JUJWROOIHBZHMG-CBYSEHNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4,5-trideuteriopyridine 生成 2,3,6-trideuteriopyridine 、 2,3,4-trideuteriopyridine
  参考文献：
  名称：

  The photochemistry of 3,4,5-trideuteriopyridine

  摘要：

  Irradiation of 3,4,5-trideuteriopyridine at 254 nm in the vapor phase results in the formation of a mixture of 2,3,4-trideuteriopyridine and 2,3,6-trideuteriopyridine. The formation of these products is consistent with a photoisomerization mechanism involving equilibrating azaprefulvene intermediates. This is the first direct evidence that pyridine vapor undergoes photoisomerization resulting in transposition of the pyridine ring atoms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.041
• 作为产物：
  描述：

  氘代吡啶-d5氮氧化物 在 三氯化磷 作用下， 生成 3,4,5-trideuteriopyridine
  参考文献：
  名称：

  The photochemistry of 3,4,5-trideuteriopyridine

  摘要：

  Irradiation of 3,4,5-trideuteriopyridine at 254 nm in the vapor phase results in the formation of a mixture of 2,3,4-trideuteriopyridine and 2,3,6-trideuteriopyridine. The formation of these products is consistent with a photoisomerization mechanism involving equilibrating azaprefulvene intermediates. This is the first direct evidence that pyridine vapor undergoes photoisomerization resulting in transposition of the pyridine ring atoms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.041

文献信息

• Potassium <i>tert</i>-butoxide promoted regioselective deuteration of pyridines
  作者：Yan Li、Chenxu Zheng、Zhi-Jiang Jiang、Jianbo Tang、Bencan Tang、Zhanghua Gao

  DOI：10.1039/d1cc07128a

  日期：——

  A regioselective deuteration at the β- and γ-position of pyridines is reported. Efficient deuteration occurred with a combination of KOtBu and DMSO-d6, replenishing the prevailing α-deuteration of the pyridine systems. Preliminary mechanistic studies suggested that the dimsyl carbanion acts as one of the key intermediates.

  报道了吡啶的 β 和 γ 位的区域选择性氘化。KO t Bu 和 DMSO- d 6的组合发生了有效的氘化，补充了吡啶系统中普遍存在的 α-氘化。初步机理研究表明，二甲基碳负离子是关键中间体之一。
• Synthesis and spectroscopic properties of isomeric trideuterio- and tetradeuterio pyridines
  作者：James W. Pavlik、Somchoke Laohhasurayotin

  DOI：10.1002/jhet.5570440637

  日期：2007.11

  The syntheses of the six possible isomeric trideuteriopyridines and the three possible isomeric tetradeuteriopyridines are described. These deuteriopyridines were characterized by their mass and NMR spectra.

  描述了六个可能的异构的三氘吡啶和三个可能的异构的四氘吡啶的合成。这些氘代吡啶通过它们的质量和NMR谱来表征。
• The Vapor-Phase Phototransposition Chemistry of Pyridine:  Deuterium Labeling Studies
  作者：James W. Pavlik、Somchoke Laohhasurayotin

  DOI：10.1021/jo7026799

  日期：2008.4.1

  The six isomeric trideuteriopyridines and the three isomeric tetradeuteriopyridines undergo phototransposition upon S0 → S2 (π, π*) excitation in the vapor phase at 254 nm. On the basis of the products formed, the six trideuteriopyridine isomers can be divided into two triads. Similarly, the three isomeric tetradeuteriopyridines also constitute a triad. Irradiation of any one member of each triad results

  在254 nm的气相中，S 0 →S 2（π，π*）激发后，六个异构的三氘吡啶和三个异构的四吡啶吡啶发生光子转移。根据形成的产物，可以将六个氘代氘代吡啶的异构体分为两个三联体。同样，三个异构的四氘代吡啶也构成一个三联体。照射每个三合会的任何一个成员会导致形成该三合会的其他两个成员。这些异构化与涉及光环化，氮在环戊烯基环的五个侧面周围迁移以及重新麦芽化的机理一致。
• C-4 Regioselective Alkylation of Pyridines Driven by Mechanochemically Activated Magnesium Metal
  作者：Chongyang Wu、Tao Ying、Hangqian Fan、Chenhui Hu、Weike Su、Jingbo Yu

  DOI：10.1021/acs.orglett.3c00684

  日期：2023.4.14

  Mechanochemically activated magnesium(0) metal as a highly active mediator driving direct C-4–H alkylation of pyridines with alkyl halides has been developed. Excellent regioselectivity and substrate scope, including those containing reducible functionalities, free amines, and alcohols, as well as biologically relevant molecules were achieved to access 4-alkylpyridine products. Preliminary mechanistic

  已经开发出机械化学活化的镁 (0) 金属作为高活性介体，驱动吡啶与烷基卤化物的直接 C-4-H 烷基化。出色的区域选择性和底物范围，包括那些含有可还原官能团、游离胺和醇的底物，以及生物相关分子，以获得 4-烷基吡啶产品。初步的机理研究表明存在自由基-自由基偶联途径。
• The photochemistry of 3,4,5-trideuteriopyridine
  作者：James W. Pavlik、Somchoke Laohhasurayotin

  DOI：10.1016/j.tetlet.2003.09.041

  日期：2003.10

  Irradiation of 3,4,5-trideuteriopyridine at 254 nm in the vapor phase results in the formation of a mixture of 2,3,4-trideuteriopyridine and 2,3,6-trideuteriopyridine. The formation of these products is consistent with a photoisomerization mechanism involving equilibrating azaprefulvene intermediates. This is the first direct evidence that pyridine vapor undergoes photoisomerization resulting in transposition of the pyridine ring atoms. (C) 2003 Elsevier Ltd. All rights reserved.