2-((S)-3-Iodo-2-methyl-propyl)-furan | 158530-56-4

• 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: 2-((S)-3-Iodo-2-methyl-propyl)-furan
• CAS: 158530-56-4
• 化学式: C₈H₁₁IO
• 分子量: 250.079
• InChiKey: XNBNNYKHTOABRE-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-((S)-3-Iodo-2-methyl-propyl)-furan 在 Celite 、 叔丁基锂 、 silver carbonate 作用下， 以 苯 为溶剂， 生成 (E)-(S)-7-Furan-2-yl-6-methyl-hept-2-en-4-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
• 作为产物：
  描述：

  (S)-3-(2-furyl)-2-methylpropyl toluene-4-sulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以99%的产率得到2-((S)-3-Iodo-2-methyl-propyl)-furan
  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