(S)-6-Furan-2-yl-2,5-dimethyl-hex-1-en-3-one | 158530-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (S)-6-Furan-2-yl-2,5-dimethyl-hex-1-en-3-one
• CAS: 158530-61-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: KSXJQNUFDBAJQA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-6-Furan-2-yl-2,5-dimethyl-hex-1-en-3-one 在 甲基二氯化铝 作用下， 以 乙醚 为溶剂， 反应 7.0h， 生成 (1R,3R,5R,6R,8R)-3,5,6-Trimethyl-11-oxa-tricyclo[6.2.1.0^1,6]undec-9-en-5-ol
  参考文献：
  名称：

  Thermodynamically controlled asymmetric induction: Applications with the intramolecular Diels-Alder reaction involving a furan diene

  摘要：

  Treatment of a variety of optically pure IMDAF precursors, containing one asymmetric centre on the sidearm, under thermodynamic conditions with MeAlCl(2) (-78 degrees C), provides cycloadducts with up to 5 asymmetric centres of known absolute stereochemistry. The minor cycloadduct can be equilibrated in the presence of MeAlCl(2) (-78 degrees C) to provide more of the major isomer. Treatment of the major cycloadduct with excess MeLi provides a decalin ring with up to 6 asymmetric centres, 5 of which are contiguous, in high enantiomeric excess.

  DOI：

  10.1016/0957-4166(94)80098-7
• 作为产物：
  描述：

  (S)-3-(furan-2-yl)-2-methylpropan-1-ol 在 4-二甲氨基吡啶 、 Celite 、 叔丁基锂 、 三乙胺 、 silver carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 生成 (S)-6-Furan-2-yl-2,5-dimethyl-hex-1-en-3-one
  参考文献：
  名称：

  Thermodynamically controlled asymmetric induction: Applications with the intramolecular Diels-Alder reaction involving a furan diene

  摘要：

  Treatment of a variety of optically pure IMDAF precursors, containing one asymmetric centre on the sidearm, under thermodynamic conditions with MeAlCl(2) (-78 degrees C), provides cycloadducts with up to 5 asymmetric centres of known absolute stereochemistry. The minor cycloadduct can be equilibrated in the presence of MeAlCl(2) (-78 degrees C) to provide more of the major isomer. Treatment of the major cycloadduct with excess MeLi provides a decalin ring with up to 6 asymmetric centres, 5 of which are contiguous, in high enantiomeric excess.

  DOI：

  10.1016/0957-4166(94)80098-7