(Z)-2-Methyl-5-(dimethylphenylsilyl)-4-nonen-3-ol | 141412-31-9

• 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: (Z)-2-Methyl-5-(dimethylphenylsilyl)-4-nonen-3-ol
• 英文别名: (Z)-5-[dimethyl(phenyl)silyl]-2-methylnon-4-en-3-ol
• CAS: 141412-31-9
• 化学式: C₁₈H₃₀OSi
• 分子量: 290.521
• InChiKey: ZOLAVJBGUFCKLJ-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (Z)-2-Methyl-5-(tributylstannyl)-4-nonen-3-yl dimethylphenylsilyl ether 在 水 、 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以79%的产率得到(Z)-2-Methyl-5-(dimethylphenylsilyl)-4-nonen-3-ol
  参考文献：
  名称：

  Studies in the Transmetalation of Cyclopropyl, Vinyl, and Epoxy Stannanes

  摘要：

  Diastereomerically pure cyclopropyl, vinyl, and epoxy stannanes have been converted to the corresponding organolithium species and trapped with a variety of electrophiles. The stereochemistry of the products was retained throughout the transmetalation-trapping sequence. The stereochemistry of the tributyltin moiety and the carbinol side chain was shown to have a dramatic influence on the rate of transmetalation. 1,4-Silyl migrations were observed for silicon groups of varying steric bulk, and crossover experiments showed the migration was an intramolecular process. Access to silanes which are difficult to prepare was achieved.

  DOI：

  10.1021/jo00118a043

文献信息

• 1,4-Silyl migration reactions. Applicability to alkyl-, vinyl-, and cyclopropylsilanes
  作者：Mark Lautens、Patrick H. M. Delanghe、Jane Betty Goh、C. H. Zhang

  DOI：10.1021/jo00038a006

  日期：1992.6

  A series of silyl protected alcohols containing a tin substituent were found to undergo transmetalation followed by silyl migration from oxygen to carbon in the presence of methyllithium.