(1R,2R,3R,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol | 1013027-64-9

• 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,2R,3R,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
• CAS: 1013027-64-9
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: LGVDAZQPWJBBGX-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 、 N-苄氧羰基-L-脯氨酸 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到(S)-benzyl 2-((1R,2R,3R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarbamoyl)-pyrrolidine-1-carboxylate
  参考文献：
  名称：

  2-Hydroxy-3-[(S)-prolinamido]pinanes as novel bifunctional organocatalysts for asymmetric aldol reactions in aqueous media

  摘要：

  Novel (S)-prolinamides with stereoisomeric 2-hydroxy-3-aminopinane units have been synthesized. In the presence of (1R,2R,3S,5R)-2-hydroxy-3-[(S)-prolinamido]pinane (5 mol %) cyclic ketones reacted with (hetero-)aromatic aldehydes in aqueous media to afford chiral aldols in high yields. The reaction had moderate to high diastereo- (dr up to 91/9) and enantioselectivities (up to 83% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.013
• 作为产物：
  描述：

  (1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以100%的产率得到(1R,2R,3R,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols

  摘要：

  Both cis- and trans-1,2-amino alcohols 5 and their N-alkylated derivatives 6 were prepared from (-)-alpha-pinene 7 as chirality source and utilized in asymmetric borane reduction of arylketones 12 employing a one-pot multi-substrate screening. The oxazaborolidine catalysts were generated in situ from amino alcohols 5 and 6 and trimethyl borate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.020