Ethyl (2S)-2-<(2S,3R)-3-Methyltetrahydrofuran-2-yl>propanonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: Ethyl (2S)-2-<(2S,3R)-3-Methyltetrahydrofuran-2-yl>propanonate
• 英文别名: ethyl (2S)-2-[(2S,3S)-3-methyloxolan-2-yl]propanoate
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: QNHLGWYEZUGTEA-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-甲基-γ-丁内酯 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.5h， 生成 Ethyl (2S)-2-<(2S,3R)-3-Methyltetrahydrofuran-2-yl>propanonate
  参考文献：
  名称：

  Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin

  摘要：

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.

  DOI：

  10.1021/jo00084a040

文献信息

• Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin
  作者：Y. Guindon、C. Yoakim、V. Gorys、W. W. Ogilvie、D. Delorme、J. Renaud、G. Robinson、J.-F. Lavallee、A. Slassi

  DOI：10.1021/jo00084a040

  日期：1994.3

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.