(1S,4S)-6-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[2.2.2]oct-5-en-2-one | 132751-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4S)-6-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[2.2.2]oct-5-en-2-one
• 英文别名: (1S,4S)-6-(2-hydroxypropan-2-yl)-4-methylbicyclo[2.2.2]oct-5-en-2-one
• CAS: 132751-30-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: BDEZJKZQDDPKEA-QPUJVOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲基二环[2.2.2]辛烷-2,6-二酮 在 selenium(IV) oxide 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 (1S,4S)-6-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[2.2.2]oct-5-en-2-one
  参考文献：
  名称：

  Regio- and stereoselective oxidation of unsaturated bicyclo[2.2.2]octanones with selenium dioxide

  摘要：

  The selenium dioxide oxidation of several unsaturated bicyclo[2.2.2]octanones has been examined in connection with the projected utility of properly functionalized products in tandem oxyanionic Cope rearrangement-S(N') transformations. The oxidations studied proved to be regioselective, with attack in the olefinic sector of each molecule occurring to the exclusion of chemical reaction alpha to the carbonyl. Stereoselectivity was also often encountered, with steric factors appearing to contribute heavily to establishing the particular configuration of the newly introduced stereogenic center.

  DOI：

  10.1021/jo00007a037

文献信息

• Regio- and stereoselective oxidation of unsaturated bicyclo[2.2.2]octanones with selenium dioxide
  作者：Leo A. Paquette、Robert E. Maleczka、Fa Yang Qiu

  DOI：10.1021/jo00007a037

  日期：1991.3

  The selenium dioxide oxidation of several unsaturated bicyclo[2.2.2]octanones has been examined in connection with the projected utility of properly functionalized products in tandem oxyanionic Cope rearrangement-S(N') transformations. The oxidations studied proved to be regioselective, with attack in the olefinic sector of each molecule occurring to the exclusion of chemical reaction alpha to the carbonyl. Stereoselectivity was also often encountered, with steric factors appearing to contribute heavily to establishing the particular configuration of the newly introduced stereogenic center.