1-(2-pyridylmethyl)benzotriazole | 159493-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(2-pyridylmethyl)benzotriazole
• 英文别名: 1-(2-pyridylmethyl)-1H-benzotriazole；1-(pyridin-2-ylmethyl)benzotriazole
• CAS: 159493-94-4
• 化学式: C₁₂H₁₀N₄
• mdl: MFCD00835270
• 分子量: 210.238
• InChiKey: CUHVSKXGJVJJRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  416.0±28.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-pyridylmethyl)benzotriazole 在 正丁基锂 、 titanium(III) chloride 、 铜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 (E)-2-(3,3-dimethylbut-1-en-1-yl) pyridine
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v
• 作为产物：
  描述：

  2-吡啶甲醇 、 1-(苯磺酰)-1H-苯并三唑 在 sodium hydride 作用下， 生成 1-(2-pyridylmethyl)benzotriazole
  参考文献：
  名称：

  Katritzky, Alan R.; Yao, Guowei; Rachwal, Stanislaw, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 757 - 764

  摘要：

  DOI：

文献信息

• Benzotriazole as a structural component in chelating and bridging heterocyclic ligands; ruthenium, palladium, copper and silver complexes
  作者：Chris Richardson、Peter J. Steel

  DOI：10.1039/b206990c

  日期：2003.2.24

  electrochemical studies of their chelated ruthenium bis(2,2′-bipyridine) complexes have shown that the benzotriazole group is a relatively electron rich component. X-Ray crystal structures are reported for one-dimensional polymeric copper and silver complexes of di(benzotriazol-1-yl)methane, mononuclear and dinuclear copper and silver complexes of 1-(2-pyridyl)benzotriazole (in which the ligand displays chelating

  已经研究了五个含有1个取代的苯并三唑亚基的N，N'-双齿配体的配位化学。对它们的螯合钌双（2,2'-联吡啶）配合物的光谱和电化学研究表明，苯并三唑基团是一个相对富电子的组分。报道了二（苯并三唑-1-基）甲烷的一维聚合物铜和银配合物，1-（2-吡啶基）苯并三唑的单核和双核铜和银配合物的X射线晶体结构（其中配体显示螯合（分别为单齿和桥联的配位方式），1-（2-吡啶基甲基）苯并三唑的桥联双核钯，铜和银配合物和1-（1-异喹啉基）苯并三唑的四核铜配合物。
• Benzotriazole-Mediated Synthesis of 2,3-Disubstituted Allylic Alcohols
  作者：Yoon Ho Kang、Chang Jae Lee、Kyongtae Kim

  DOI：10.1021/jo000469c

  日期：2001.3.1
• <i>catena</i>-Poly[[dichloridomercury(II)]-μ-1-(2-pyridylmethyl)-1<i>H</i>-benzotriazole]: the effect of different metal centers on the self-assembly of coordination complexes
  作者：Chun-Sen Liu、Li-Ming Zhou、Liang-Qi Guo、Song-Tao Ma、Shao-Ming Fang

  DOI：10.1107/s0108270108038146

  日期：2008.12.15

  To further investigate the relationship between the structures of benzotriazol-1-yl-based pyridyl ligands and their complexes, a new linear one-dimensional Hg-II coordination polymer, [HgCl2(C12H10N4)](n), with the 1-(2-pyridylmethyl)1H-benzotriazole (L) ligand was obtained through the reaction of L with HgCl2. In this complex, each HgII center within the one-dimensional chain is coordinated by two chloride anions as well as by one pyridine and one benzotriazole N-atom donor of two distinct L ligands in a distorted tetrahedral geometry, forming a linear one-dimensional chain running along the [010] direction. Weak C-H center dot center dot center dot pi and pi-pi stacking interactions link the one-dimensional motifs to generate an overall two-dimensional network parallel to the ( 100) plane. Comparison of the structural differences with previous findings suggests that the presence of different metal centers may plays an important role in the construction of such supramolecular frameworks.
• Katritzky, Alan R.; Yao, Guowei; Rachwal, Stanislaw, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 757 - 764
  作者：Katritzky, Alan R.、Yao, Guowei、Rachwal, Stanislaw

  DOI：——

  日期：——
• Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation
  作者：Alan R. Katritzky、Dai Cheng、Scott A. Henderson、Jianqing Li

  DOI：10.1021/jo980616v

  日期：1998.9.1

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.