(1E,4E)-4-methyl-1-trimethylsilyl-1,4-hexadien-3-one | 81255-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,4E)-4-methyl-1-trimethylsilyl-1,4-hexadien-3-one
• 英文别名: (1E,4E)-4-methyl-1-(trimethylsilyl)hexa-1,4-dien-3-one；(1E,4E)-4-methyl-1-trimethylsilylhexa-1,4-dien-3-one
• CAS: 81255-90-5
• 化学式: C₁₀H₁₈OSi
• 分子量: 182.338
• InChiKey: YARWDVPRWIILSG-KHHFIZIMSA-N

物化性质

• 沸点：
  123 °C(Press: 13 Torr)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1E,4E)-4-methyl-1-trimethylsilyl-1,4-hexadien-3-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以75%的产率得到2,3-二甲基-2-环戊烯酮
  参考文献：
  名称：

  Polymer-Mediated Reactions. A Nazarov-Like Cyclization

  摘要：

  The polymer PEDOT+ mediates a Nazarov-like cyclization of dienones, in an heterogeneous system and in hydrocarbon solvents. The polymer-mediated reactions show clear differences in product formation when compared to the same reaction with tosic acid, or when compared to reports in the literature. Comparable or improved yields are observed, as well as the ability to give a Nazarov product in cases where treatment with acid fails to give cyclization, or leads to an undesirable rearrangement. In addition, the ability to recycle the polymer makes this a potentially useful protocol for an important organic chemical reaction.

  DOI：

  10.1055/s-0030-1261194
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 在 nickel(IV) oxide 、 氯化铵 作用下， 以 乙醚 为溶剂， 生成 (1E,4E)-4-methyl-1-trimethylsilyl-1,4-hexadien-3-one
  参考文献：
  名称：

  Silicon-directed Nazarov cyclization

  摘要：

  DOI：

  10.1021/ja00373a055

文献信息

• Silicon-DirectedNazarov Reactions II. Preparation and Cyclization of ?-Silyl-substituted Divinyl Ketones
  作者：Todd K. Jones、Scott E. Denmark

  DOI：10.1002/hlca.19830660802

  日期：1983.12.14

  Two general methods for the preparation of β-silyl-substituted divinyl ketones have been developed starting from either α, β-unsaturated aldehydes or simple ketones. Anhydrous FeCl3 induces the cyclization to cyclopentenones under mild conditions and in good yields with predictable and complete control over the position of the double bond in the five-membered ring. The observed effects of substituents

  从α，β-不饱和醛或简单的酮开始，已经开发了两种制备β-甲硅烷基取代的二乙烯基酮的通用方法。无水FeCl 3在温和条件下以高收率诱导环化成环戊烯酮，并且可预测和完全控制五元环中双键的位置。观察到的取代基对速率的影响可以通过速率决定性阳离子电环化来解释。已显示甲硅烷基取代会阻碍反应。
• DENMARK, S. E.;JONES, T. K., J. AMER. CHEM. SOC., 1982, 104, N 9, 2642-2645
  作者：DENMARK, S. E.、JONES, T. K.

  DOI：——

  日期：——
• JONES, T. K.;DENMARK, S. E., HELV. CHIM. ACTA, 1983, 66, N 8, 2377-2396
  作者：JONES, T. K.、DENMARK, S. E.

  DOI：——

  日期：——
• Polymer-Mediated Reactions. A Nazarov-Like Cyclization
  作者：Michael Smith、Christopher Pavlik、Martha Morton、Michael Invernale、Ian Berghorn、Gregory Sotzing

  DOI：10.1055/s-0030-1261194

  日期：2011.9

  The polymer PEDOT+ mediates a Nazarov-like cyclization of dienones, in an heterogeneous system and in hydrocarbon solvents. The polymer-mediated reactions show clear differences in product formation when compared to the same reaction with tosic acid, or when compared to reports in the literature. Comparable or improved yields are observed, as well as the ability to give a Nazarov product in cases where treatment with acid fails to give cyclization, or leads to an undesirable rearrangement. In addition, the ability to recycle the polymer makes this a potentially useful protocol for an important organic chemical reaction.
• Silicon-directed Nazarov cyclization
  作者：S. E. Denmark、T. K. Jones

  DOI：10.1021/ja00373a055

  日期：1982.5