acetic acid 1-(2-azido-phenyl)-4,5,5-triphenyl-pent-4-en-2-ynyl ester | 1020202-95-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: acetic acid 1-(2-azido-phenyl)-4,5,5-triphenyl-pent-4-en-2-ynyl ester
• 英文别名: [1-(2-Azidophenyl)-4,5,5-triphenylpent-4-en-2-ynyl] acetate
• CAS: 1020202-95-2
• 化学式: C₃₁H₂₃N₃O₂
• 分子量: 469.543
• InChiKey: HSUFVOPNERUKTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetic acid 1-(2-azido-phenyl)-4,5,5-triphenyl-pent-4-en-2-ynyl ester 、 甲基溴化镁 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以38%的产率得到1-azido-2-(3-methyl-4,5,5-triphenyl-penta-1,2,4-trienyl)-benzene
  参考文献：
  名称：

  Allenyl Azide Cycloaddition Chemistry. 2,3-Cyclopentennelated Indole Synthesis through Indolidene Intermediates

  摘要：

  The thermal, photochemical, and photochemical/CuI-mediated cascade cyclizations of a range of substituted 1-(2-azidophenyl)-3-alkenylallenes are described. These reactions provide both 1,2- and 2,3-cyclopentennelated indole products in varying ratios. In most cases, high regioselectivity for the 2,3-annelated isomer can be achieved under the hv/CuI conditions. Computational studies of this multistep reaction support the intermediacy of indolidene intermediates whose electrocyclizations (with or without copper present) define the regioselectivity branch point in the sequence.

  DOI：

  10.1021/jo900659w
• 作为产物：
  描述：

  (1,2-二苯基-丁-1-烯-3-炔基)-苯 、 乙酸酐 、 2-叠氮基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以78%的产率得到acetic acid 1-(2-azido-phenyl)-4,5,5-triphenyl-pent-4-en-2-ynyl ester
  参考文献：
  名称：

  Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved Regioselectivity

  摘要：

  Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modestto-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.

  DOI：

  10.1021/ol800429j