3-(phenyldimethylsilyl)cyclohex-2-enone | 82202-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(phenyldimethylsilyl)cyclohex-2-enone
• 英文别名: 3-dimethylphenylsilyl-2-cyclohexen-1-one；3-[Dimethyl(phenyl)silyl]cyclohex-2-en-1-one
• CAS: 82202-13-9
• 化学式: C₁₄H₁₈OSi
• 分子量: 230.382
• InChiKey: OCTGGSIHGBBGTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-二甲基苯基甲硅烷基-1-环己烯基三甲基甲硅烷基醚 在 air 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以31%的产率得到3-(phenyldimethylsilyl)cyclohex-2-enone
  参考文献：
  名称：

  Silicon-Induced Ene-Type Reaction in the Thermal Conversion of Enolates to β-Silyl Enones with Molecular Dioxygen

  摘要：

  Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with molecular dioxygen in toluene at 110 degrees C produced the corresponding conjugated enones in yields up to 88% yield. The reaction of the same type failed on replacement of the silyl group at the C-3 position with an isopropyl group. These results indicate the existence of an unprecedented silicon-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed.

  DOI：

  10.1021/ol800007v

文献信息

• The synthesis of αβ-unsaturated ketones from β-silylenones and β-silylynones
  作者：Ian Fleming、David A. Perry

  DOI：10.1016/s0040-4020(01)93277-6

  日期：——

  Conjugate addition, followed by alkylation, bromination and desilyl-bromination make the β-silylketone (4) an a3d3-synthon (5) and the β-silylynone (6) a 2a3d3-synthon (7).

  共轭加成，然后进行烷基化，溴化和去甲硅烷基溴化反应，使β-甲硅烷基酮（4）成为3 d 3-合成子（5）和β-甲硅烷基酮（6）成为2a 3 d 3-合成子（7）。
• Synthesis of cyclic β-silylenones via oxidative rearrangement of tertiary α-hydroxy allylsilanes with PCC
  作者：Xia Wu、Jian Lei、Zhen Lei Song

  DOI：10.1016/j.cclet.2010.10.018

  日期：2011.3

  Abstract An oxidative rearrangement of cyclic tertiary α -hydroxy allylsilanes has been carried out in refluxing ClCH 2 CH 2 Cl with pyridinium chlorochromate (PCC). The reaction provides a convenient method to synthesize cyclic β -silylenones in modest to excellent yields.

  摘要在氯仿吡啶鎓氯化铬（PCC）回流ClCH 2 CH 2 Cl的条件下，进行了环状叔α-羟基烯丙基硅烷的氧化重排。该反应提供了以适中至优异的产率合成环状β-硅烯酮的简便方法。
• FLEMING, I.;PERRY, D. A., TETRAHEDRON, 1981, 37, N 23, 4027-4034
  作者：FLEMING, I.、PERRY, D. A.

  DOI：——

  日期：——
• Silicon-Induced Ene-Type Reaction in the Thermal Conversion of Enolates to β-Silyl Enones with Molecular Dioxygen
  作者：Jih Ru Hwu、Chien Hsien Chen、Chuan-I Hsu、Asish R. Das、Yen Cheng Li、Lung Ching Lin

  DOI：10.1021/ol800007v

  日期：2008.5.1

  Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with molecular dioxygen in toluene at 110 degrees C produced the corresponding conjugated enones in yields up to 88% yield. The reaction of the same type failed on replacement of the silyl group at the C-3 position with an isopropyl group. These results indicate the existence of an unprecedented silicon-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed.