{3-[3-(2-azido-phenyl)-1-methyl-propa-1,2-dienyl]-6,6-dimethyl-cyclohex-2-enyloxy}-triisopropyl-silane | 1020202-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: {3-[3-(2-azido-phenyl)-1-methyl-propa-1,2-dienyl]-6,6-dimethyl-cyclohex-2-enyloxy}-triisopropyl-silane
• CAS: 1020202-76-9
• 化学式: C₂₇H₄₁N₃OSi
• 分子量: 451.728
• InChiKey: SQHJDRCPYYJZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.49
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {3-[3-(2-azido-phenyl)-1-methyl-propa-1,2-dienyl]-6,6-dimethyl-cyclohex-2-enyloxy}-triisopropyl-silane 以 甲苯 为溶剂， 反应 0.5h， 以51%的产率得到3,1,1-trimethyl-2,3-dihydro-1H-indolo[1,2-a]indole
  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)-3-(4,4-dimethyl-3-triisopropylsilanyloxy-cyclohex-enyl)-prop-2-ynyl acetate 、 甲基溴化镁 在 copper(l) iodide 、 lithium bromide 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以89%的产率得到{3-[3-(2-azido-phenyl)-1-methyl-propa-1,2-dienyl]-6,6-dimethyl-cyclohex-2-enyloxy}-triisopropyl-silane
  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

文献信息

• Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved Regioselectivity
  作者：Ken S. Feldman、D. Keith Hester、Carlos Silva López、Olalla Nieto Faza

  DOI：10.1021/ol800429j

  日期：2008.4.1

  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.
• Allenyl Azide Cycloaddition Chemistry. 2,3-Cyclopentennelated Indole Synthesis through Indolidene Intermediates
  作者：Ken S. Feldman、D. Keith Hester、Malliga R. Iyer、Paul J. Munson、Carlos Silva López、Olalla Nieto Faza

  DOI：10.1021/jo900659w

  日期：2009.7.17

  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.