4-(Dimethylphenylsilyl)but-2-yn-1-ol | 137200-58-9

• 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: 4-(Dimethylphenylsilyl)but-2-yn-1-ol
• 英文别名: 4-(dimethylphenylsilyl)-2-butyn-1-ol；4-[Dimethyl(phenyl)silyl]but-2-yn-1-ol
• CAS: 137200-58-9
• 化学式: C₁₂H₁₆OSi
• 分子量: 204.344
• InChiKey: SRKRTNJXJBBSPF-UHFFFAOYSA-N

物化性质

• 沸点：
  313.6±22.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(Dimethylphenylsilyl)but-2-yn-1-ol 在 TEA 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 4-(dimethylphenylsilyl)-2-butynyl iodide
  参考文献：
  名称：

  Cyclooctane or cyclohexane annulations based on intramolecular additions of allylsilanes to conjugated dienones

  摘要：

  The scope and limitations of alkenyl dienone cyclizations for the formation of fused cyclooctane or cyclohexane systems are described.

  DOI：

  10.1021/jo00012a034
• 作为产物：
  描述：

  苯基二甲基氯硅烷 在 碘 正丁基锂 、 magnesium 作用下， 反应 4.83h， 生成 4-(Dimethylphenylsilyl)but-2-yn-1-ol
  参考文献：
  名称：

  Cyclooctane or cyclohexane annulations based on intramolecular additions of allylsilanes to conjugated dienones

  摘要：

  The scope and limitations of alkenyl dienone cyclizations for the formation of fused cyclooctane or cyclohexane systems are described.

  DOI：

  10.1021/jo00012a034

文献信息

• Palladium(II)-Catalyzed Cycloisomerization of Functionalized 1,5-Hexadienes
  作者：Björn Nelson、Wolf Hiller、Annett Pollex、Martin Hiersemann

  DOI：10.1021/ol201795w

  日期：2011.8.19

  Scope and limitations of the Pd(II)-catalyzed cycloisomerization of functionalized 1,5-hexadienes have been studied. In situ NMR experiments indicate a challenging competition between various reaction pathways. A careful balance between substrate structure, nature of the precatalyst, and reaction conditions was required to gain access to a useful building block for sesquiterpene total synthesis.
• Sequential Homoaldolization. Cuprate Rearrangement in a Stereoselective Synthesis of Stannyl Dienes: Application to the Synthesis of the Western C10-C15 Subunit of (.+-.)-Tylosin Aglycon
  作者：Patrick Le Menez、Valerie Fargeas、Isabelle Berque、Jacques Poisson、Janick Ardisson、Jean-Yves Lallemand、Ange Pancrazi

  DOI：10.1021/jo00117a007

  日期：1995.6

  A stereospecific synthesis of stannyl diene 5, corresponding to the C10-C15 fragment of(+/-)-tylosin aglycon 2, was reported. Silyl carbamate 16, submitted to the Hoppe homoaldolization conditions with propanal, gave the anti aldol product 17 in 89% yield. Further treatment including oxidation of the silyl group led to lactone 21. The corresponding dihydrofuran 23 was then transformed into vinylstannane 25, via an efficient Kocienski rearrangement. An iodine exchange was performed on 25 and followed by a Stille coupling reaction with tributylstannyl acetylide. Stannyl cupration of the resulting silylated enyne 27 led in 44% yield to a 1:1 mixture of the desired (E,E)-stannyl diene 5b and the unexpected (E,Z) isomer 29. The same reaction performed on desilylated enyne 28 delivered in 85% yield the pure (E,E)-stannyl diene 5.
• MAJETICH, GEORGE;HULL, KENNETH;CASARES, ADA M.;KHETANI, VIKRAM, J. ORG. CHEM., 56,(1991) N2, C. 3958-3973
  作者：MAJETICH, GEORGE、HULL, KENNETH、CASARES, ADA M.、KHETANI, VIKRAM

  DOI：——

  日期：——
• Cyclooctane or cyclohexane annulations based on intramolecular additions of allylsilanes to conjugated dienones
  作者：George Majetich、Kenneth Hull、Ada M. Casares、Vikram Khetani

  DOI：10.1021/jo00012a034

  日期：1991.6

  The scope and limitations of alkenyl dienone cyclizations for the formation of fused cyclooctane or cyclohexane systems are described.