3-(tert-butyldimethylsilyloxy)-5,6-epoxy-1-phenylhexane | 461640-15-3

• 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: 3-(tert-butyldimethylsilyloxy)-5,6-epoxy-1-phenylhexane
• 英文别名: Tert-butyl-dimethyl-[1-(oxiran-2-yl)-4-phenylbutan-2-yl]oxysilane
• CAS: 461640-15-3
• 化学式: C₁₈H₃₀O₂Si
• 分子量: 306.521
• InChiKey: MIYQLCZIGYLNDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯硫酚 、 3-(tert-butyldimethylsilyloxy)-5,6-epoxy-1-phenylhexane 在 三(五氟苯基)硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到4-[Tert-butyl(dimethyl)silyl]oxy-6-phenyl-1-phenylsulfanylhexan-2-ol
  参考文献：
  名称：

  Highly efficient cleavage of epoxides catalyzed by B(C6F5)3

  摘要：

  A highly effective protocol for ring opening of epoxides with allyl and propargyl alcohols, aniline and thiophenol in the presence of catalytic amounts of B(C6F5)(3) has been developed. Benzyl, tetrahydropyranyl, tert-butyldimethyl silyl protecting groups were stable under the reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00703-7
• 作为产物：
  描述：

  5,6-epoxy-1-phenylhexan-3-ol 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到3-(tert-butyldimethylsilyloxy)-5,6-epoxy-1-phenylhexane
  参考文献：
  名称：

  3-Silyloxytetrahydrofurans via sulfoxonium ylide reactions with α-silyloxyepoxides

  摘要：

  alpha-Silyloxyepoxides were found to undergo sulfoxonium ylide induced ring-opening, followed by silyl-migration and intramolecular S(N)2 reaction, resulting in 3-silyloxytetrahydrofurans. Studies on the scope and utility of this transformation are described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.113

文献信息

• Highly efficient cleavage of epoxides catalyzed by B(C6F5)3
  作者：S. Chandrasekhar、Ch. Raji Reddy、B. Nagendra Babu、G. Chandrashekar

  DOI：10.1016/s0040-4039(02)00703-7

  日期：2002.5

  A highly effective protocol for ring opening of epoxides with allyl and propargyl alcohols, aniline and thiophenol in the presence of catalytic amounts of B(C6F5)(3) has been developed. Benzyl, tetrahydropyranyl, tert-butyldimethyl silyl protecting groups were stable under the reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 3-Silyloxytetrahydrofurans via sulfoxonium ylide reactions with α-silyloxyepoxides
  作者：Paul S. Sabila、Yanke Liang、Amy R. Howell

  DOI：10.1016/j.tetlet.2007.09.113

  日期：2007.11

  alpha-Silyloxyepoxides were found to undergo sulfoxonium ylide induced ring-opening, followed by silyl-migration and intramolecular S(N)2 reaction, resulting in 3-silyloxytetrahydrofurans. Studies on the scope and utility of this transformation are described. (C) 2007 Elsevier Ltd. All rights reserved.