(1R,2R)-2-endo-hydroxy-2-exo-(N,N-dimethylaminopropyl)-1,3,3-trimethylbicyclo<2.2.1>heptane

• 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)-2-endo-hydroxy-2-exo-(N,N-dimethylaminopropyl)-1,3,3-trimethylbicyclo<2.2.1>heptane
• 英文别名: (1R,2R,4S)-2-[3-(dimethylamino)propyl]-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• 化学式: C₁₅H₂₉NO
• 分子量: 239.401
• InChiKey: YNYYIEIAUNKJON-CFVMTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 、 3-dimethylaminopropyllithium 在 cerium(III) chloride 作用下， 生成 (1R,2R)-2-endo-hydroxy-2-exo-(N,N-dimethylaminopropyl)-1,3,3-trimethylbicyclo<2.2.1>heptane
  参考文献：
  名称：

  从（+）-樟脑和（-）-杏仁酮一步合成高度光学选择性的新型旋光性氨基醇

  摘要：

  从CeCl 3活化的（+）-樟脑脂和（-）-甲ench酮以及N-官能化的有机锂化合物制备了新的旋光氨基醇。所获得的氨基醇以高收率和高达64％的对映选择性催化将二乙基锌添加到苯甲醛中。

  DOI：

  10.1016/s0957-4166(97)00182-1

文献信息

• Anhydrous cerium(III) chloride — Effect of the drying process on activity and efficiency
  作者：Vladimir Dimitrov、Kalina Kostova、Miroslav Genov

  DOI：10.1016/s0040-4039(96)01479-7

  日期：1996.9

  The activity and efficiency of anhydrous CeCl3 depend strongly on the drying procedure. Deactivation of CeCl3 occurs during the drying process as a result of hydrolysis by the hydrate water, when heating above 90 degrees C. The highly active CeCl3, prepared by an improved drying procedure, is demonstrated to activate rapidly (in catalytic and stoichiometric amounts) ketones at room temperature, providing excellent addition of organometallic reagents. Copyright (C) 1996 Elsevier Science Ltd
• Cerium(III) chloride as catalytic and stoichiometric promoter of the quantitative addition of organometallic reagents to (+)-camphor and (-)-fenchone
  作者：Vladimir Dimitrov、Svetoslav Bratovanov、Svetlana Simova、Kalina Kostova

  DOI：10.1016/s0040-4039(00)73475-7

  日期：1994.9

  Quantitative addition of organolithium and Grignard reagents to camphor (1) and fenchone (2) proceeds via precomplexation of the ketone with CeCl3 at room temperature. Excellent addition using catalytic or substoichiometric amounts of CeCl3 is demonstrated for the first time.
• Highly diastereoselective synthesis of new optically active aminoalcohols in one step from (+)-camphor and (−)-fenchone
  作者：Miroslav Genov、Kalina Kostova、Vladimir Dimitrov

  DOI：10.1016/s0957-4166(97)00182-1

  日期：1997.6

  New optically active aminoalcohols have been prepared from CeCl3-activated (+)-camphor and (−)-fenchone and N-functionalized organolithium compounds. The aminoalcohols obtained catalyze the addition of diethylzinc to benzaldehyde in high yields and enantioselectivities up to 64%.

  从CeCl 3活化的（+）-樟脑脂和（-）-甲ench酮以及N-官能化的有机锂化合物制备了新的旋光氨基醇。所获得的氨基醇以高收率和高达64％的对映选择性催化将二乙基锌添加到苯甲醛中。