1-(2-丁烯酰基)-1H-苯并三唑 | 55889-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 1-(2-丁烯酰基)-1H-苯并三唑
• 英文名称: 1-(2-Butenoyl)-1H-benzotriazole
• 英文别名: 1-(benzotriazol-1-yl)but-2-en-1-one
• CAS: 55889-32-2
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: QYJRVRUTXXZMAD-UHFFFAOYSA-N

物化性质

• 熔点：
  93-97 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 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

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  1-(2-丁烯酰基)-1H-苯并三唑 在 sodium azide 、 iron(III) chloride hexahydrate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 以74%的产率得到crotonoyl azide
  参考文献：
  名称：

  FeCl₃ · 6H₂O-Catalyzed Acceleration of the Acylation of Sodium Azide withN-Acylbenzotriazoles

  摘要：

  [image omitted] Catalyzed by ferric chloride hexahydrate (FeCl3 center dot 6H2O), the acylation of sodium azide with N-acylbenzotriazoles was greatly accelerated in a mixed solvent of acetone and water. Thus, good to excellent yields of a variety of acyl azides were obtained at room temperature in a short time. Furthermore, because of the complete conversion of N-acylbenzotriazoles and the easy removal of the by-product, purification by column chromatography was no longer required, which made the protocol suitable for large-scale preparation.

  DOI：

  10.1080/00397911.2010.505698
• 作为产物：
  描述：

  T406石油添加剂 、 巴豆酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到1-(2-丁烯酰基)-1H-苯并三唑
  参考文献：
  名称：

  N-酰基和 N-磺酰基苯并三唑与多种硝基化合物的镍催化还原交叉偶联：快速获得酰胺和磺酰胺

  摘要：

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。

  DOI：

  10.1021/acs.orglett.1c03535

文献信息

• Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
  作者：Erdong Qu、Shangzhang Li、Jin Bai、Yan Zheng、Wanfang Li

  DOI：10.1021/acs.orglett.1c03535

  日期：2022.1.14

  Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。
• Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides
  作者：Bo-Liang Zhao、Da-Ming Du

  DOI：10.1039/c3ob42137f

  日期：——

  A novel highly enantioselective one-pot dithiolation through sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides catalysed by squaramide has been developed. This organocatalysed reaction proceeded well in high to excellent yields (up to >99%) to afford useful bioactive β-sulfated thioester derivatives with high enantioselectivities (up to 96% ee).

  已经开发了一种新的高度对映选择性的一锅二硫代反应，其通过硫醇-迈克尔加成/硫酯与方酰胺催化的α，β-不饱和N-酰化琥珀酰亚胺的硫代酯化反应而开发。该有机催化的反应以高至优异的产率（高达> 99％）良好地进行，以提供有用的具有高对映选择性（高达96％ee）的生物活性β-硫酸化硫酯衍生物。
• Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation
  作者：Ye-Fu Zhu、Bo-Le Wei、Jiao-Jiao Wei、Wen-Qiong Wang、Wei-Bin Song、Li-Jiang Xuan

  DOI：10.1016/j.tetlet.2019.03.063

  日期：2019.4

  A palladium-catalyzed oxidative dehydrogenation reaction in the presence of AMS and base to synthesize pyrazolones and pyrazoles was identified. This method can be utilized to a wide range of substrates, operates under mild react conditions and can give high yields. We believe it could be used as an alternative protocol for the classical dehydrogenation reactions.

  在AMS和碱存在下，钯催化的氧化脱氢反应得以合成吡唑啉酮和吡唑。该方法可用于多种底物，在温和的反应条件下运行，并能提供高收率。我们相信它可以用作经典脱氢反应的替代方案。
• Facile and Highly Regiospecific Synthesis of 2-Aryl-Substituted Pyrazolidin-3-ones from α,β-Unsaturated <i>N</i>-Acylbenzotriazoles and Arylhydrazines
  作者：Xiaoxia Wang、Wencun Wang、Yihang Wen、Liang He、Xiangming Zhu

  DOI：10.1055/s-0028-1083159

  日期：——

  The bis-addition of arylhydrazines to α,β-unsaturated N-acylbenzotriazoles to form heterocyclic compounds was achieved in refluxing THF by using triethylamine as promoter. The reaction was highly regioselective and various 2-aryl-substituted pyrazolidin-3-ones were obtained in moderate to good yields.

  以三乙胺为促进剂，在回流THF中实现了芳基肼与α,β-不饱和N-酰基苯并三唑的双加成形成杂环化合物。该反应具有高度的区域选择性，并且以中等至良好的产率获得了各种 2-芳基取代的 pyrazolidin-3-one。
• Highly regioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
  作者：Xuefei Zou、Xiaoxia Wang、Cungui Cheng、Lichun Kong、Hui Mao

  DOI：10.1016/j.tetlet.2006.03.110

  日期：2006.5

  Friedel–Crafts alkylation rather than acylation of indoles was realized with α,β-unsaturated acylbenzotriazoles catalyzed by samarium(III) iodide under reflux in anhydrous THF. The reaction was highly regioselective, and a series of new 3-substituted indole derivatives were obtained in moderate to good yields with the potential to be further transformed into various indole derivatives due to the presence

  碘化sa（III）在无水THF中回流时，用α，β-不饱和酰基苯并三唑实现了吲哚的Friedel-Crafts烷基化而不是酰化。该反应是高度区域选择性的，并且以中等至良好的产率获得了一系列新的3-取代的吲哚衍生物，由于存在活性酰基苯并三唑部分，因此有可能进一步转化成各种吲哚衍生物。