(R*)-2-<(R*)-phenyl(trimethylsilyl)methyl>-1-hexanol | 144038-46-0

• 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: (R*)-2-<(R*)-phenyl(trimethylsilyl)methyl>-1-hexanol
• 英文别名: (2R)-2-[(R)-phenyl(trimethylsilyl)methyl]hexan-1-ol
• CAS: 144038-46-0
• 化学式: C₁₆H₂₈OSi
• 分子量: 264.483
• InChiKey: JRKDPORPMCDZAG-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Trimethyl-[2-(phenyl-phenylsulfanyl-methyl)-hexyloxy]-silane 在 lithium di-tert-butylbiphenylide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以95%的产率得到(R*)-2-<(R*)-phenyl(trimethylsilyl)methyl>-1-hexanol
  参考文献：
  名称：

  Regiochemically and stereochemically defined synthesis of allylsilanes

  摘要：

  Allyl sulfides containing a siloxy or hydroxy group at appropriate positions were successfully converted by two methods into two types of allylsilanes with almost complete stereo- and regiocontrol. In one method, an allyllithium was generated from the siloxy compound after which the silyl group migrated from oxygen to the carbanionic site. The reaction of 4-[[(trimethylsilyl)oxy]methyl]-3-methyl-2-cyclohexenyl phenyl sulfide with lithium di-tert-butylbiphenylide (LDBB) led to an exclusive formation of (1R*,2R*)-2-methyl-2-(trimethylsilyl)-3-cyclohexene-1-methanol. The second method involved the silylation of an oxyanion-carbanion. Using this method, (1R*,4R*)-1-methyl-4-(trimethylsilyl)-2-cyclohexene-1-methanol was obtained by treating its lithium alkoxide with LDBB followed by silylation with chlorotrimethylsilane.

  DOI：

  10.1021/ja00073a018

文献信息

• Regio- and Stereo-defined Synthesis of Organosilicon Compounds via Rearrangement of Silyl Group
  作者：Shinji Marumoto、Isao Kuwajima

  DOI：10.1246/cl.1992.1421

  日期：1992.8

  On treating with LDBB, 2-substituted 3-phenylthioalkyl silyl ethers were converted to the corresponding 3-silylated alkanols with high anti selectivity. Application to silyl ethers containing allylic sulfide moieties provided a useful methodology for the regio- and stereo-defined synthesis of allylsilanes.

  在用LDBB处理时，2-取代的3-苯硫代烷基甲硅烷基醚以高抗选择性转化为相应的3-甲硅烷基化烷醇。应用于含有烯丙基硫化物部分的甲硅烷基醚为烯丙基硅烷的区域和立体定义合成提供了一种有用的方法。