5-methyl-3-bromo-2-triisopropylsilyloxyfuran | 1068579-63-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-methyl-3-bromo-2-triisopropylsilyloxyfuran
• 英文别名: (3-Bromo-5-methylfuran-2-yl)oxy-tri(propan-2-yl)silane
• CAS: 1068579-63-4
• 化学式: C₁₄H₂₅BrO₂Si
• 分子量: 333.341
• InChiKey: NLERVHCJNCTVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘十六烷 、 5-methyl-3-bromo-2-triisopropylsilyloxyfuran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (3-Hexadecyl-5-methylfuran-2-yl)oxy-tri(propan-2-yl)silane
  参考文献：
  名称：

  General, Regiodefined Access to α-Substituted Butenolides through Metal−Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid

  摘要：

  A variety of alpha-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.

  DOI：

  10.1021/jo8015924
• 作为产物：
  描述：

  三异丙基硅基三氟甲磺酸酯 、 3-溴-5-甲基-5H-呋喃-2-酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到5-methyl-3-bromo-2-triisopropylsilyloxyfuran
  参考文献：
  名称：

  General, Regiodefined Access to α-Substituted Butenolides through Metal−Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid

  摘要：

  A variety of alpha-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.

  DOI：

  10.1021/jo8015924

文献信息

• General, Regiodefined Access to α-Substituted Butenolides through Metal−Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid
  作者：John Boukouvalas、Richard P. Loach

  DOI：10.1021/jo8015924

  日期：2008.10.17

  A variety of alpha-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.