Ethyl (4R)-2,4-dimethyl-6-hydroxyhex-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (4R)-2,4-dimethyl-6-hydroxyhex-2-enoate
• 英文别名: ethyl (E,4R)-6-hydroxy-2,4-dimethylhex-2-enoate
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: NONYQGMVPHQGNI-KGOFQHAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl (4R)-2,4-dimethyl-6-hydroxyhex-2-enoate 在 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到Ethyl (2S)-2-<(2S,3R)-3-Methyltetrahydrofuran-2-yl>-2-iodopropanonate
  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
• 作为产物：
  描述：

  乙氧甲酰基亚乙基三苯基 、 α-甲基-γ-丁内酯 在 二异丁基氢化铝 作用下， 生成 Ethyl (4R)-2,4-dimethyl-6-hydroxyhex-2-enoate
  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