1-[3-(4-chloro-phenyl)-acryloyl]-1H-benzotriazole | 57710-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-[3-(4-chloro-phenyl)-acryloyl]-1H-benzotriazole
• 英文别名: p-chlorocinnamoyl benzotriazolyl amide；1-(4-Chlorocinnamoyl)-benzotriazol；1-(Benzotriazol-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one
• CAS: 57710-83-5
• 化学式: C₁₅H₁₀ClN₃O
• 分子量: 283.717
• InChiKey: XJISVNOCGLRJPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-[3-(4-chloro-phenyl)-acryloyl]-1H-benzotriazole 在 sodium azide 、 iron(III) chloride hexahydrate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.08h， 以90%的产率得到4-chlorocinnamoyl 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

文献信息

• An Approach to the Efficient Syntheses of Chiral Phosphino- Carboxylic Acid Esters
  作者：Renta Jonathan Chew、Kristel Sepp、Bin-Bin Li、Yongxin Li、Peng-Cheng Zhu、Nguan Soon Tan、Pak-Hing Leung

  DOI：10.1002/adsc.201500638

  日期：2015.10.12

  addition of diarylphosphines with N-enoylbenzotriazoles and analogues is described. Chiral phosphine products are obtained in 100% atom economy and without cumbersome protection–deprotection manipulations. The obtained products can be subsequently transformed to bear various functionalities, including phosphino-carboxylic esters which play critical roles in catalysis and as synthetic aids. Anti-tumour activities

  催化加氢磷酸化反应是当今最可持续的化学转化之一。在此，描述了二芳基膦与N-烯酰基苯并三唑和类似物的钯催化的不对称PH加成。手性膦产品的原子经济性为100％，无需繁琐的保护-去保护操作。随后可以将获得的产物转化为具有各种功能，包括在催化中和作为合成助剂发挥关键作用的膦基羧酸酯。已经探索了相应的金膦复合物的抗肿瘤活性，为癌症治疗中的现有化学疗法研究做出了贡献。
• 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。
• SmI₃-Catalyzed Addition of Amines to<font>α</font>,<font>β</font>-Unsaturated<i>N</i>-Acylbenzotriazoles
  作者：Xiaoxia Wang、Liang He、Zhifang Li、Wencun Wang、Junhua Liu

  DOI：10.1080/00397910802431180

  日期：2009.2.9

  The addition of amines to ,-unsaturated N-acylbenzotriazoles could be catalyzed by samarium triiodide (SmI3) at ambient temperature. ,-Unsaturated aliphatic N-acylbenzotriazoles afforded bis-addition products (-amino amides), whereas N-cinnamoylbenzotriazoles gave acylated products (cinnamoylamides) exclusively.
• Tu, Ya Wei; Zhou, Lie Jin; Lv, Xin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 4, p. 435 - 439
  作者：Tu, Ya Wei、Zhou, Lie Jin、Lv, Xin、Wang, Xiao Xia

  DOI：——

  日期：——
• FeCl₃ · 6H₂O-Catalyzed Acceleration of the Acylation of Sodium Azide with<i>N</i>-Acylbenzotriazoles
  作者：Zhiyun Zhong、Jieling Hu、Xiaoxia Wang、Junhua Liu、Longfeng Zhang

  DOI：10.1080/00397911.2010.505698

  日期：2011.8.15

  [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.