α-trimethylsilylethenyl butyl ketone | 155102-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-trimethylsilylethenyl butyl ketone
• 英文别名: 2-trimethylsilyl-1-hepten-3-one；2-Trimethylsilylhept-1-en-3-one
• CAS: 155102-12-8
• 化学式: C₁₀H₂₀OSi
• 分子量: 184.354
• InChiKey: ITOUOGMLCAFYNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-trimethylsilylethenyl butyl ketone 、 苯甲醛 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到2-(Hydroxy-phenyl-methyl)-hept-1-en-3-one
  参考文献：
  名称：

  α-三甲基甲硅烷基-α,β-不饱和酮作为 1-炔基阴离子合成物的用途

  摘要：

  在醛的存在下用四丁基氟化铵处理 α-三甲基甲硅烷基-α,β-不饱和酮，以良好的收率提供了 α-(1-羟烷基)-α,β-不饱和酮。反应通过烯丙醇酯进行。新方法成功应用于由α-三甲基甲硅烷基-α,β-不饱和酯合成α-(1-羟烷基)-α,β-不饱和酯。

  DOI：

  10.1246/cl.1994.1211
• 作为产物：
  描述：

  三甲基乙炔基硅 在 titanium(IV) isopropylate 、 4 A molecular sieve 、 氧气 、 tetraphenylporphyrin 作用下， 反应 11.0h， 生成 α-trimethylsilylethenyl butyl ketone
  参考文献：
  名称：

  Highly Regio- and Diastereoselective One-Pot Synthesis of Silyl Epoxy Alcohols and Vinylsilanes by Direct Hydroxy-Epoxidation

  摘要：

  A direct synthesis of silyl epoxy alcohols from vinyl silanes is described. It consists of the regioselective ene reaction of the vinylsilanes with singlet oxygen, which proceeds with predominant hydrogen abstraction at the position geminal to the silyl group. The resulting silyl allylic hydroperoxides were treated, without isolation, subsequently with Ti(O-i-Pr)(4) to afford the silyl epoxy alcohols in good yields and very high diastereomeric ratios, which ranged from 93:7 to greater than 97:3. Alternatively, the vinylsilanes were photooxygenated directly in the presence of the titanium catalyst and the silyl epoxy alcohols obtained in good yields. The method was applied to di- and trisubstituted acyclic vinylsilanes with a methyl group geminal to silicon and cyclic derivatives all give consistently good results. In this novel hydroxy-epoxidation, the regioselectivity of the singlet oxygen ene reaction as well as the diastereoselectivity of the oxygen transfer can be controlled by the steering effects of the silyl group.

  DOI：

  10.1021/jo00091a021

文献信息

• One-Pot Synthesis of α-Trimethylsilyl Enones from Vinylsilanes
  作者：Waldemar Adam、Markus J. Richter

  DOI：10.1055/s-1994-25433

  日期：——

  Photooxygenation of vinylsilanes in the presence of acetic anhydride and pyridine afforded α-trimethylsilyl enones 1 in moderate to good yields. Since the required starting materials are readily available, the present approach constitutes a useful alternative to existing methods for the preparation of α-trimethylsilyl enones 1.

  在乙酸酐和吡啶的存在下，通过乙烯基硅烷的光氧化反应可以中等至良好的产率获得α-三甲基硅基烯酮1。由于所需的起始材料易于获得，因此本方法为现有制备α-三甲基硅基烯酮1的方法提供了一个有用的替代方案。
• Matsumoto Kozo, Oshima Koichiro, Utimoto Kiitiro, Chem. Lett, (1994) N 7, S 1211-1214
  作者：Matsumoto Kozo, Oshima Koichiro, Utimoto Kiitiro

  DOI：——

  日期：——