(1R,2S,3S,5R)-2-methylaminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol | 1003078-70-3

• 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: (1R,2S,3S,5R)-2-methylaminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
• 英文别名: (1R,2S,3S,5R)-6,6-dimethyl-2-(methylaminomethyl)bicyclo[3.1.1]heptane-2,3-diol
• CAS: 1003078-70-3
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: VCPWXWPCBYILJF-SDNRWEOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2S,3S,5R)-2-[(benzylmethylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以86%的产率得到(1R,2S,3S,5R)-2-methylaminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
  参考文献：
  名称：

  Synthesis and application of monoterpene-based chiral aminodiols

  摘要：

  Primary, secondary and tertiary aminodiols were synthetized regio- and stereoselectively from (-)-alpha-pinene 1 via a-pinene oxide 2, (-)-trans-pinocarveol 3 and key intermediate epoxy alcohol 4. N-Benzyl derivative 5 was transformed to spiro-fused oxazolidine 13 in a highly regioselective ring closure. Aminodiols and their derivatives 5-13 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde, resulting in chiral 1-phenyl- 1-propanol. The substituent effect on the nitrogen was studied in detail and the best enantioselectivity was observed in the case of N-methyl-N-benzyl-substituted derivative 8. The phenomenon was interpreted by using molecular modelling at an ab initio level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.065