2-[5-Tri(propan-2-yl)silyloxyfuran-3-yl]propan-2-ol | 1196150-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-[5-Tri(propan-2-yl)silyloxyfuran-3-yl]propan-2-ol
• 英文别名: 2-[5-tri(propan-2-yl)silyloxyfuran-3-yl]propan-2-ol
• CAS: 1196150-95-4
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: DRUZVFOPIVLOPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[5-Tri(propan-2-yl)silyloxyfuran-3-yl]propan-2-ol 、 diethyl (Z)-2-[2-[tert-butyl(dimethyl)silyl]oxy-1-methylindol-4-yl]but-2-enedioate 在 2,6-二叔丁基吡啶 、 zinc(II) iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以1.715 g的产率得到diethyl (2R,3R,5R,9S,17R)-8,8,11-trimethyl-10-oxo-5-tri(propan-2-yl)silyloxy-4-oxa-11-azapentacyclo[7.6.1.12,5.03,7.012,16]heptadeca-1(16),6,12,14-tetraene-2,17-dicarboxylate
  参考文献：
  名称：

  Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction

  摘要：

  Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction Is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.

  DOI：

  10.1021/ol902173g
• 作为产物：
  描述：

  丙酮 、 4-Bromo-2-triisopropylsilyloxyfuran 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.5h， 以87%的产率得到2-[5-Tri(propan-2-yl)silyloxyfuran-3-yl]propan-2-ol
  参考文献：
  名称：

  Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction

  摘要：

  Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction Is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.

  DOI：

  10.1021/ol902173g

文献信息

• Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction
  作者：John A. Brailsford、Ryan Lauchli、Kenneth J. Shea

  DOI：10.1021/ol902173g

  日期：2009.11.19

  Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction Is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.