1-t-butyldiphenylsilyloxy-5-trimethylsilyloxyhexane | 158527-87-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-t-butyldiphenylsilyloxy-5-trimethylsilyloxyhexane
• 英文别名: Tert-butyl-diphenyl-(5-trimethylsilyloxyhexoxy)silane
• CAS: 158527-87-8
• 化学式: C₂₅H₄₀O₂Si₂
• 分子量: 428.762
• InChiKey: XSFFMSNWGWFBHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-t-butyldiphenylsilyloxy-5-trimethylsilyloxyhexane 在 水 、 氢化铝 作用下， 以 正己烷 为溶剂， 以69%的产率得到6-((tert-butyldiphenylsilyl)oxy)hexan-2-ol
  参考文献：
  名称：

  Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers

  摘要：

  The selective cleavage of primary and secondary trimethylsilyl (TMS), triisopropylsilyl (TIPS), tert-butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) ethers with neutral alumina under very mild conditions is described. The method involves utilization of the support, previously activated by heating at 80 degrees C/0.1 torr for 16 h and later deactivated with variable amounts of water (1.5-4.5%), in 50:1 ratio with regard to the substrate and in the presence of non-polar solvents, like hexane. The deprotection rate depends on the steric bulkiness of the silicon substituents, following the order TMS > > TBDMS approximate to TIPS > TBDPS, as well as on the type of the attached carbon. The procedure can discriminate between different silyl groups located at equivalent positions of the same molecule affording the corresponding monoprotected alcohols in very good yields.

  DOI：

  10.1016/s0040-4020(01)85572-1
• 作为产物：
  描述：

  6-((tert-butyldiphenylsilyl)oxy)hexan-2-ol 、 三甲基氯硅烷 在 咪唑 作用下， 以62%的产率得到1-t-butyldiphenylsilyloxy-5-trimethylsilyloxyhexane
  参考文献：
  名称：

  Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers

  摘要：

  The selective cleavage of primary and secondary trimethylsilyl (TMS), triisopropylsilyl (TIPS), tert-butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) ethers with neutral alumina under very mild conditions is described. The method involves utilization of the support, previously activated by heating at 80 degrees C/0.1 torr for 16 h and later deactivated with variable amounts of water (1.5-4.5%), in 50:1 ratio with regard to the substrate and in the presence of non-polar solvents, like hexane. The deprotection rate depends on the steric bulkiness of the silicon substituents, following the order TMS > > TBDMS approximate to TIPS > TBDPS, as well as on the type of the attached carbon. The procedure can discriminate between different silyl groups located at equivalent positions of the same molecule affording the corresponding monoprotected alcohols in very good yields.

  DOI：

  10.1016/s0040-4020(01)85572-1

文献信息

• Feixas Joan, Capdevila Anna, Guerrero Angel, Tetrahedron, 50 (1994) N 28, S 8539-8550
  作者：Feixas Joan, Capdevila Anna, Guerrero Angel

  DOI：——

  日期：——
• Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers
  作者：Joan Feixas、Anna Capdevila、Angel Guerrero

  DOI：10.1016/s0040-4020(01)85572-1

  日期：1994.1

  The selective cleavage of primary and secondary trimethylsilyl (TMS), triisopropylsilyl (TIPS), tert-butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) ethers with neutral alumina under very mild conditions is described. The method involves utilization of the support, previously activated by heating at 80 degrees C/0.1 torr for 16 h and later deactivated with variable amounts of water (1.5-4.5%), in 50:1 ratio with regard to the substrate and in the presence of non-polar solvents, like hexane. The deprotection rate depends on the steric bulkiness of the silicon substituents, following the order TMS > > TBDMS approximate to TIPS > TBDPS, as well as on the type of the attached carbon. The procedure can discriminate between different silyl groups located at equivalent positions of the same molecule affording the corresponding monoprotected alcohols in very good yields.