1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethan-1-one
• 英文别名: 1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethanone；1-phenyl-2-(1H-triazol-1-yl)ethanone；1-phenyl-2-(triazol-1-yl)ethanone
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: PTAVLXRFVPFISM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 1-phenyl-2-(1H-triazol-1-yl)ethanol
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and molecular modeling studies of novel 1-phenyl/1-(4-chlorophenyl)-2-(1H-triazol-1-yl)ethanol ester derivatives

  摘要：

  A series of new ester derivatives were synthesized by the reaction of various acids with 1-phenyl/1-(4-chlorophenyl)-2-(1H-triazol-1-yl)ethanol and in vivo screened for their anticonvulsant activity. The title compounds were screened against MES and ScM seizure tests according to a modified version of the Epilepsy Therapy Screening Program (ETSP) protocol of the National Institutes of Health (NIH). Their neurotoxic effects were evaluated by the rotarod test. All the compounds showed protection against MES and/or ScM-induced seizures at 30 mg/kg without neurotoxicity. More compounds were found active in the ScM test and at lower dose than the MES test. Physicochemical and pharmacokinetic profiles of the compounds were predicted by QikProp. Using molecular docking approach we tried to get insights into their possible anticonvulsant mechanisms.

  DOI：

  10.1007/s00044-018-2225-6
• 作为产物：
  描述：

  1-azidostyrene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-phenyl-2-(1H-1,2,3-triazol-1-yl)ethan-1-one
  参考文献：
  名称：

  CC和CN键形成偶联反应中的叠氮En烯物种。

  摘要：

  乙烯基叠氮化物与三氟化硼活化的Koser的高价碘试剂反应生成叠氮-烯类物质。这些先前未知的叠氮基-olo烯类物质在温和条件下与芳族化合物，烯丙基三甲基硅烷和唑类有效反应，无需过渡金属催化剂，形成CC和CN键即可生成各种α-官能化的酮。拟议的叠氮en烯物种的中间性得到了光谱学研究的支持。

  DOI：

  10.1021/acs.orglett.9b03824

文献信息

• Enolonium Species-Umpoled Enolates
  作者：Shlomy Arava、Jayprakash N. Kumar、Shimon Maksymenko、Mark A. Iron、Keshaba N. Parida、Peter Fristrup、Alex M. Szpilman

  DOI：10.1002/anie.201610274

  日期：2017.3.1

  Enolonium species/iodo(III)enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α‐C−O, α‐C−N, α‐C−C, and α‐carbon–halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes

  羰基化合物的olo烯物种/碘（III）烯醇盐被认为是多种高碘碘诱导的酮化学转化的中间体，包括α-C-O，α-C-N，α-C-C和α-碳-卤化物键的形成，但从未被表征过。我们报告说，这些难以捉摸的块状烯醇化物可能被制成离散的种类，在-78°C下可稳定几分钟，并报告了此类物质的首次光谱鉴定。结果表明，en烯类是C-O，C-N，C-Cl和C-C键形成反应中的直接中间体。我们的结果为设计各种新的转化开辟了化学空间。我们展示了olo烯物种与异戊二烯基，巴豆基，肉桂基和烯丙基硅烷反应的能力，具有绝对的区域选择性，产率高达92％。
• Method for producing 1-substituted-1,2,3- triazole derivative
  申请人：——

  公开号：US20030069419A1

  公开（公告）日：2003-04-10

  A method for producing a compound of the formula: 1 (1) in a secondary or tertiary alcohol in the presence of a base, or (2) in the absence of a base is provided. According to this method, a 1-substituted-1,2,3-triazole compound having a tyrosine kinase inhibitory action can be produced efficiently in a high yield at an industrial large scale by a convenient method

  提供了一种制备以下公式化合物的方法： 1 (1) 在二级或三级醇中，在碱的存在下，或 (2) 在无碱的情况下进行。根据这种方法，可以通过一种方便的方法，在工业大规模下高效并以高收率地制备具有酪氨酸激酶抑制作用的1-取代-1,2,3-三唑化合物
• α-<i>N</i>-Heteroarylation and α-Azidation of Ketones via Enolonium Species
  作者：Atul A. More、Gulab K. Pathe、Keshaba N. Parida、Shimon Maksymenko、Yuriy B. Lipisa、Alex M. Szpilman

  DOI：10.1021/acs.joc.7b03058

  日期：2018.2.16

  Enolonium species, resulting from the umpolung of ketone enolates by Koser’s hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4–5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.

  由Koser的由三氟化硼活化的高价碘试剂对酮烯醇化物进行封固而产生的olo烯类物质，与多种氮杂环反应形成α-胺化酮。反应温和且在4-5小时内完成。另外，使用三甲基甲硅烷基叠氮化物作为叠氮化物亲核试剂的方便来源，进行en物种的α-叠氮化。
• Alkylation and Acylation of the 1, 2, 3-Triazole Ring
  作者：Shunsaku OHTA、Ikuo KAWASAKI、Takahiro UEMURA、Masayuki YAMASHITA、Tomomichi YOSHIOKA、Satoshi YAMAGUCHI

  DOI：10.1248/cpb.45.1140

  日期：——

  Trimethylsilylaion of 1, 2, 3-triazole regioselectively proceeded to give 2-trimethylsilyl-2H-1, 2, 3-triazole, which was treated with primary alkyl halides in the presence of tetrabutylammonium fluoride to give 1-alkyl-1H-1, 2, 3-triazoles as a sole product. 1-Methyl-5-substituted 1H-1, 2, 3-triazoles were prepared by alkylation of 5-lithio-1-methyl-1H-1, 2, 3-triazole, and 1-methyl-4-substituted 1H-1, 2, 3-triazoles were obtained by alkylaiton of 4-lithio-1-methyl-5-phenylthio-1H-1, 2, 3-triazole followed by reductive desulfurization.

  三甲基硅基化的 1, 2, 3-三唑选择性地生成了 2-三甲基硅基-2H-1, 2, 3-三唑，该化合物在四丁基氟铵存在下与初级烷基卤化物反应，生成 1-烷基-1H-1, 2, 3-三唑作为唯一产物。通过烷基化 5-锂化-1-甲基-1H-1, 2, 3-三唑制备了 1-甲基-5-取代的 1H-1, 2, 3-三唑，1-甲基-4-取代的 1H-1, 2, 3-三唑则通过烷基化 4-锂化-1-甲基-5-苯硫基-1H-1, 2, 3-三唑后进行还原脱硫得到。
• [EN] SMALL MOLECULE INHIBITORS OF FIBROSIS<br/>[FR] INHIBITEURS DE FIBROSE À PETITES MOLÉCULES
  申请人：CALIFORNIA INST BIOMEDICAL RES

  公开号：WO2016094570A1

  公开（公告）日：2016-06-16

  Described herein are compounds and compositions for the treatment of a fibrotic disease.

  本文描述了用于治疗纤维化疾病的化合物和组合物。