2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylpropan-1-one | 189343-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylpropan-1-one
• 英文别名: 2-(benzotriazol-1-yl)-1-phenylpropan-1-one
• CAS: 189343-70-2
• 化学式: C₁₅H₁₃N₃O
• mdl: MFCD00961577
• 分子量: 251.288
• InChiKey: BDGIPQDLLSFZBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylpropan-1-one 在 正丁基锂 、 amberlyst-15 作用下， 以 乙醚 、 苯 为溶剂， 反应 60.5h， 生成 1-苯基-1-丙炔 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles

  摘要：

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.

  DOI：

  10.1021/jo962291t
• 作为产物：
  描述：

  T406石油添加剂 、 苯丙酮 在 碘 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以92%的产率得到2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide

  摘要：

  We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate to good yields and high regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.008

文献信息

• Gas-phase thermolysis of benzotriazole derivatives: part 1—synthesis ofα-N(1)- andN(2)-benzotriazolyl ketones and kinetics and mechanism of their gas-phase pyrolysis
  作者：Hicham H. Dib、Nouria A. Al-Awadi、Yehia A. Ibrahim、Osman M. E. El-Dusouqui

  DOI：10.1002/poc.717

  日期：2004.4

  1-(Benzotriazol-1-yl)propan-2-one (1) and 3-(benzotriazol-1-yl)butan-2-one (2), and their respective phenyl analogues 2-(benzotriazol-1-yl)-1-phenylethanone (3) and 2-(benzotriazol-1-yl)-1-phenylpropan-1-one (4), together with 1-cyanobenzotriazole (5) and 1-(benzotriazol-2-yl)propan-2-one (6), were synthesized and then subjected to gas-phase thermolysis. The products of complete pyrolysis of 1–4 were

  1-（苯并三唑-1-基）丙烷-2-酮（1）和3-（苯并三唑-1-基）丁-2-酮（2）以及它们各自的苯基类似物2-（苯并三唑-1-基） -1-苯基乙酮（3）和2-（苯并三唑-1-基）-1-苯基丙烷-1-酮（4），以及1-氰基苯并三唑（5）和1-（苯并三唑-2-基）丙烷-2合成一个（6），然后进行气相热解。完全热解的产品1 - 4除了2-取代的吲哚或2，3-二取代的吲哚外，还发现苯胺是苯胺。还研究了本发明化合物的气相热消除反应的动力学，这是对苯并三唑的首次研究。阿累尼乌斯指数前因子（A / s -1）和活化能（E a / kJ mol -1）分别是：（1）为10.03和156.7，（2）为9.93和158.0，（（12）为12.68和169.9 3），9.45和144.4对于（4）和15.40和163.6为（5）。化合物6似乎通过热允许的1,5-基团迁移进入化合物而异构化1在热解之前。动力学和产物分析的结果参考涉及稳定（N
• Hypoiodite‐Catalyzed Oxidative α‐C−N Coupling of Ketones with Imides and Azoles
  作者：Mayuko Tsukahara、Muhammet Uyanik、Kazuaki Ishihara

  DOI：10.1002/adsc.202300716

  日期：2023.8.15

  Herein, we report a direct method for the synthesis of α-imidoketones and α-azolylketones via hypoiodite-catalyzed oxidative α-C−N coupling of ketones with the corresponding imides and azoles, respectively. The use of inorganic base additives such as cesium carbonate in the presence of 18-crown-6 as a phase transfer catalyst was crucial to induce high reactivity. Control experiments revealed that the

  在此，我们报道了一种通过次碘酸盐催化酮与相应酰亚​​胺和唑的氧化 α-C−N 偶联直接合成 α-亚胺酮和 α-唑基酮的方法。在 18-crown-6 存在下使用碳酸铯等无机碱添加剂作为相转移催化剂对于诱导高反应性至关重要。对照实验表明，碱性添加剂不仅可能促进高周转次碘酸盐催化，而且还参与偶联配偶体的活化。
• Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide
  作者：Wenlin Chen、Rulong Yan、Dong Tang、Shuaibo Guo、Xu Meng、Baohua Chen

  DOI：10.1016/j.tet.2012.07.008

  日期：2012.9

  We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate to good yields and high regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
• A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles
  作者：Alan R. Katritzky、Jin Wang、Nazira Karodia、Jianqing Li

  DOI：10.1021/jo962291t

  日期：1997.6.13

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.