[1-(2-Azidophenyl)-3-[4,4-dimethyl-3-(2-trimethylsilylethoxymethoxy)cyclohexen-1-yl]prop-2-ynyl] acetate | 1161422-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-(2-Azidophenyl)-3-[4,4-dimethyl-3-(2-trimethylsilylethoxymethoxy)cyclohexen-1-yl]prop-2-ynyl] acetate
• CAS: 1161422-44-1
• 化学式: C₂₅H₃₅N₃O₄Si
• 分子量: 469.656
• InChiKey: BKYNYCHWTWBTIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1-(2-Azidophenyl)-3-[4,4-dimethyl-3-(2-trimethylsilylethoxymethoxy)cyclohexen-1-yl]prop-2-ynyl] acetate 、 甲基溴化镁 在 copper(l) iodide 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以86%的产率得到
  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-azido-phenyl)-prop-2-ynyl acetate 、 [2-(3-iodo-6,6-dimethyl-cyclohex-2-enyloxymethoxy)-ethyl]-trimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 16.0h， 以63%的产率得到[1-(2-Azidophenyl)-3-[4,4-dimethyl-3-(2-trimethylsilylethoxymethoxy)cyclohexen-1-yl]prop-2-ynyl] acetate
  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