3-hydroxy-11-(tetrahydropyran-2-yloxy)dodecane-5,7-dione

• 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: 3-hydroxy-11-(tetrahydropyran-2-yloxy)dodecane-5,7-dione
• 英文别名: (11S)-3-hydroxy-11-(oxan-2-yloxy)dodecane-5,7-dione
• 化学式: C₁₇H₃₀O₅
• 分子量: 314.422
• InChiKey: JBIMKODBCJHZPR-CBCUQQMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-11-(tetrahydropyran-2-yloxy)dodecane-5,7-dione 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 (2R,6S,8S)-2-ethyl-8-methyl-1,7-dioxaspiro<5.5>undecan-4-one 、 (2S,6R,8S)-2-ethyl-8-methyl-1,7-dioxaspiro<5.5>undecan-4-one 、 (2R,6R,8S)-2-ethyl-8-methyl-1,7-dioxaspiro<5.5>undecan-4-one
  参考文献：
  名称：

  Syntheses of 2-ethyl-8-methyl-1,7-dioxaspiro[5.5]undecanols

  摘要：

  Synthetic approaches to ring- and side-chain hydroxy derivatives of the 2-ethyl-8-methyl-1,7-dioxaspiro-[5.5]undecane system 8 are described. Alkylation reactions of diethyl 3-oxopentanedioate, pentane-2,4-dione and acetone N,N-dimethylhydrazone have been employed. Appropriate choices of enantiomeric iodides in the alkylation sequences, sometimes followed by asymmetric dihydroxylation of derived hydroxyenones, have permitted access to key enantiomers of these alcohols, which have been fully characterised by H-1 and C-13 NMR spectroscopy, gas chromatographic-mass spectrometric methods, and chiral gas chromatography.

  DOI：

  10.1039/p19950000901
• 作为产物：
  描述：

  丙醛 、 (S)-8-(Tetrahydro-pyran-2-yloxy)-nonane-2,4-dione 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以3.06 g的产率得到3-hydroxy-11-(tetrahydropyran-2-yloxy)dodecane-5,7-dione
  参考文献：
  名称：

  Syntheses of 2-ethyl-8-methyl-1,7-dioxaspiro[5.5]undecanols

  摘要：

  Synthetic approaches to ring- and side-chain hydroxy derivatives of the 2-ethyl-8-methyl-1,7-dioxaspiro-[5.5]undecane system 8 are described. Alkylation reactions of diethyl 3-oxopentanedioate, pentane-2,4-dione and acetone N,N-dimethylhydrazone have been employed. Appropriate choices of enantiomeric iodides in the alkylation sequences, sometimes followed by asymmetric dihydroxylation of derived hydroxyenones, have permitted access to key enantiomers of these alcohols, which have been fully characterised by H-1 and C-13 NMR spectroscopy, gas chromatographic-mass spectrometric methods, and chiral gas chromatography.

  DOI：

  10.1039/p19950000901

文献信息

• Syntheses of 2-ethyl-8-methyl-1,7-dioxaspiro[5.5]undecanols
  作者：Mark F. Jacobs、Bill D. Suthers、Achim Hübener、William Kitching

  DOI：10.1039/p19950000901

  日期：——

  Synthetic approaches to ring- and side-chain hydroxy derivatives of the 2-ethyl-8-methyl-1,7-dioxaspiro-[5.5]undecane system 8 are described. Alkylation reactions of diethyl 3-oxopentanedioate, pentane-2,4-dione and acetone N,N-dimethylhydrazone have been employed. Appropriate choices of enantiomeric iodides in the alkylation sequences, sometimes followed by asymmetric dihydroxylation of derived hydroxyenones, have permitted access to key enantiomers of these alcohols, which have been fully characterised by H-1 and C-13 NMR spectroscopy, gas chromatographic-mass spectrometric methods, and chiral gas chromatography.