9c,12c-octadecadienol, tBDMS

• 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: 9c,12c-octadecadienol, tBDMS
• 英文别名: tert-butyl-dimethyl-[(9Z,12Z)-octadeca-9,12-dienoxy]silane
• 化学式: C₂₄H₄₈OSi
• 分子量: 380.73
• InChiKey: MUKSRZAZTRGHLB-HDXUUTQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  亚麻醇 、 叔丁基二甲基氯硅烷 在 P(MeNCH₂CH₂)3N 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以88%的产率得到9c,12c-octadecadienol, tBDMS
  参考文献：
  名称：

  Nonionic Superbase-Catalyzed Silylation of Alcohols

  摘要：

  Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)(3)N, Ib, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 degrees C and on rare occasions in DMF from 24 to 80 degrees C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of Ib as a catalyst, tertiary alcohols were recovered unchanged.

  DOI：

  10.1021/jo9701492