2-(trimethylsilyl)androsta-1,4-diene-3,17-dione | 1025691-45-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2-(trimethylsilyl)androsta-1,4-diene-3,17-dione
• 英文别名: (8R,9S,10S,13S,14S)-10,13-dimethyl-2-trimethylsilyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 1025691-45-5
• 化学式: C₂₂H₃₂O₂Si
• 分子量: 356.58
• InChiKey: HHZNICSYTUTLRD-HSDNQCAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-acetoxy-1α-(trimethylsilyl)androsta-2,4-dien-17-one 在 air 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以51%的产率得到2-(trimethylsilyl)androsta-1,4-diene-3,17-dione
  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

• 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.