<2R-(2α(S*),3aα,4α,7α,7aα)>-2-Chlor-β-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)-oxy>-benzolethanamin | 133163-15-2

• 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: <2R-(2α(S*),3aα,4α,7α,7aα)>-2-Chlor-β-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)-oxy>-benzolethanamin
• 英文别名: (2S)-2-(2-chlorophenyl)-2-[[(1R,2S,4R,6S,7R)-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decan-4-yl]oxy]ethanamine
• CAS: 133163-15-2
• 化学式: C₂₀H₂₈ClNO₂
• 分子量: 349.901
• InChiKey: XQHUEOGKGVJRLW-GVVKDUARSA-N

物化性质

• 沸点：
  444.8±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2R-(2α(S*),3aα,4α,7α,7aα)>-2-Chlor-β-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)-oxy>-benzolethanamin 在 盐酸 作用下， 以 甲醇 为溶剂， 以91%的产率得到<2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-2-methoxy-7,8,8-trimethyl-4,7-methanobenzofuran
  参考文献：
  名称：

  Aminoalkohole, 2. Mitt.: Ein Verfahren zur Herstellung enantiomerenreiner pharmakologisch aktiver ?-Aminoalkohole

  摘要：

  A synthesis of beta-aminoalcohols is described starting from racemic or enantiomerically pure alpha-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminium hydride yielded O-protected beta-aminoalcohols. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected aminoalcohols were separated. Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure beta-aminoalcohols or their corresponding hydrochlorides.

  DOI：

  10.1007/bf00813211
• 作为产物：
  描述：

  <2R-(2α(R*/S*),3aα,4α,7α,7aα)>-2-Chloro-α-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>benzeneacetonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以24.8%的产率得到<2R-(2α(R*),3aα,4α,7α,7aα)>-2-Chlor-β-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)-oxy>-benzolethanamin
  参考文献：
  名称：

  Aminoalkohole, 2. Mitt.: Ein Verfahren zur Herstellung enantiomerenreiner pharmakologisch aktiver ?-Aminoalkohole

  摘要：

  A synthesis of beta-aminoalcohols is described starting from racemic or enantiomerically pure alpha-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminium hydride yielded O-protected beta-aminoalcohols. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected aminoalcohols were separated. Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure beta-aminoalcohols or their corresponding hydrochlorides.

  DOI：

  10.1007/bf00813211

文献信息

• Aminoalkohole, 3. Mitt. Ein Verfahren zur Herstellung von enantiomerenreinen pharmakologisch aktiven N-substituierten ?-Aminoalkoholen
  作者：C. R. Noe、M. Knollm�ller、P. G�rtner、W. Fleischhacker、E. Katikarides

  DOI：10.1007/bf00807429

  日期：1995.5

  A synthesis of N-substituted beta-aminoalcohols is described starting from enantiomerically pure O-MBF- or O-MBE-protected beta-aminoalcohols which can be prepared via LiAlH4 reduction of O-protected cyanohydrines.
• Aminoalkohole, 2. Mitt.: Ein Verfahren zur Herstellung enantiomerenreiner pharmakologisch aktiver ?-Aminoalkohole
  作者：C. R. Noe、M. Knollm�ller、P. G�rtner、W. Fleischhacker、E. Katikarides

  DOI：10.1007/bf00813211

  日期：1995.4

  A synthesis of beta-aminoalcohols is described starting from racemic or enantiomerically pure alpha-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminium hydride yielded O-protected beta-aminoalcohols. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected aminoalcohols were separated. Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure beta-aminoalcohols or their corresponding hydrochlorides.