1-[(1R,2R)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]propan-2-one | 251319-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[(1R,2R)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]propan-2-one
• 英文别名: 1-[(1R,2R,4S)-2-hydroxy-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]propan-2-one
• CAS: 251319-23-0
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: PJFADTYOSKJHAF-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1R,2R)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]propan-2-one 在 lithium aluminium tetrahydride 作用下， 生成 小茴香醇 、 (1R,2R)-2-[(2S)-2-hydroxypropyl]-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Preparation of Chiral Hydroxy Carbonyl Compounds and Diols by Ozonolysis of Olefinic Isoborneol and Fenchol Derivatives: Characterization of Stable Ozonides by1H-,13C-, and17O-NMR and Electrospray Ionization Mass Spectrometry

  摘要：

  The allylic and homoallylic alcohols 1-8, prepared from (+)-camphor and (-)-fenchone, were ozonized in Et2O at -78 and treated with Et3N or LiAlH4 to give the chiral hydroxy carbonyl compounds 9-16 and the diols 17-24, respectively (Scheme I). In the case of the diols 19 and WI the formation of new chiral centers proceeded with high diastereoselectivity. These diols were prepared highly diastereoselectively also by LiAlH4 reduction of the hydroxy carbonyl compounds 11 and 16a, respectively (Scheme 2). The absolute configuration of the new chiral centers in 19 and 24 was determined by X-ray and NMR methods. The ozonization of compounds 2, 3, 7, and 8 provided the relatively stable hydroxy-substituted 1,2,4-trioxolane derivatives (ozonides) 37-40 (Scheme 5) which were characterized by H-1- and C-13-NMR spectra. ESI-MS, and natural-abundance O-17-NMR spectra.

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1385::aid-hlca1385>3.0.co;2-y
• 作为产物：
  描述：

  (1R)-1,3,3-trimethyl-2-(2-methylprop-2-enyl)bicyclo[2.2.1]heptan-2-ol 在 氧气 、 臭氧 、 三乙胺 作用下， 以 乙醚 为溶剂， 以8.28 g的产率得到1-[(1R,2R)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]propan-2-one
  参考文献：
  名称：

  Preparation of Chiral Hydroxy Carbonyl Compounds and Diols by Ozonolysis of Olefinic Isoborneol and Fenchol Derivatives: Characterization of Stable Ozonides by1H-,13C-, and17O-NMR and Electrospray Ionization Mass Spectrometry

  摘要：

  The allylic and homoallylic alcohols 1-8, prepared from (+)-camphor and (-)-fenchone, were ozonized in Et2O at -78 and treated with Et3N or LiAlH4 to give the chiral hydroxy carbonyl compounds 9-16 and the diols 17-24, respectively (Scheme I). In the case of the diols 19 and WI the formation of new chiral centers proceeded with high diastereoselectivity. These diols were prepared highly diastereoselectively also by LiAlH4 reduction of the hydroxy carbonyl compounds 11 and 16a, respectively (Scheme 2). The absolute configuration of the new chiral centers in 19 and 24 was determined by X-ray and NMR methods. The ozonization of compounds 2, 3, 7, and 8 provided the relatively stable hydroxy-substituted 1,2,4-trioxolane derivatives (ozonides) 37-40 (Scheme 5) which were characterized by H-1- and C-13-NMR spectra. ESI-MS, and natural-abundance O-17-NMR spectra.

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1385::aid-hlca1385>3.0.co;2-y

文献信息

• Preparation of Chiral Hydroxy Carbonyl Compounds and Diols by Ozonolysis of Olefinic Isoborneol and Fenchol Derivatives: Characterization of Stable Ozonides by1H-,13C-, and17O-NMR and Electrospray Ionization Mass Spectrometry
  作者：Kalina Kostova、Vladimir Dimitrov、Svetlana Simova、Manfred Hesse

  DOI：10.1002/(sici)1522-2675(19990908)82:9<1385::aid-hlca1385>3.0.co;2-y

  日期：1999.9.8

  The allylic and homoallylic alcohols 1-8, prepared from (+)-camphor and (-)-fenchone, were ozonized in Et2O at -78 and treated with Et3N or LiAlH4 to give the chiral hydroxy carbonyl compounds 9-16 and the diols 17-24, respectively (Scheme I). In the case of the diols 19 and WI the formation of new chiral centers proceeded with high diastereoselectivity. These diols were prepared highly diastereoselectively also by LiAlH4 reduction of the hydroxy carbonyl compounds 11 and 16a, respectively (Scheme 2). The absolute configuration of the new chiral centers in 19 and 24 was determined by X-ray and NMR methods. The ozonization of compounds 2, 3, 7, and 8 provided the relatively stable hydroxy-substituted 1,2,4-trioxolane derivatives (ozonides) 37-40 (Scheme 5) which were characterized by H-1- and C-13-NMR spectra. ESI-MS, and natural-abundance O-17-NMR spectra.