(R)-2-(tetrahydropyran-2-yloxy)dodec-10-en-6-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (R)-2-(tetrahydropyran-2-yloxy)dodec-10-en-6-one
• 英文别名: (E,2R)-2-(oxan-2-yloxy)dodec-10-en-6-one
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: CTOMSGSKMSPERY-OVBWGHLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(tetrahydropyran-2-yloxy)dodec-10-en-6-one 在 盐酸 、 AD-mix-α 、 甲基磺酰胺 作用下， 生成 2-<(2S,6S,8R,12S)-(8-methyl-1,7-dioxaspiro<5.5>undecan-2-yl)>ethanol
  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：

  反式-5-溴-2-戊烯 、 丙酮二甲腙 、 1-iodo<3-tetrahydro-2H-pyran-2-yl>oxybutane 在 正丁基锂 、 silica gel 作用下， 生成 (R)-2-(tetrahydropyran-2-yloxy)dodec-10-en-6-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

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.