1,7,7-trimethyl-3-(pyrid-2-ylmethyl)bicyclo[2.2.1]heptan-2-one | 267228-98-8

• 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: 1,7,7-trimethyl-3-(pyrid-2-ylmethyl)bicyclo[2.2.1]heptan-2-one
• CAS: 267228-98-8
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: JSRDGZKHFUPVNP-QVNUIZJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲基锂 、 1,7,7-trimethyl-3-(pyrid-2-ylmethyl)bicyclo[2.2.1]heptan-2-one 以 四氢呋喃 、 乙醚 为溶剂， 以21%的产率得到1,7,7-trimethyl-2-methyl-3-(pyrid-2-ylmethyl)bicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  (+)-Camphor-derived amino alcohols as ligands for the catalytic enantioselective addition of diethylzinc to benzaldehydes

  摘要：

  1,7,7-Tiimethyl-3-(pyrid-2-ylmethyl) bicyclo[2.2.1]heptan-2-ol 4 and its 2-phenyl, 2-methyl and 2-butyl analogs 5-7 were synthesized, characterized and used as ligands for the addition of diethylzinc to benzaldehydes. Best results were attained with 5 mol% of amino alcohol trans-4 (2-exo,3-endo), in hexane/toluene at rt. Thus, (IS)-1-phenylpropanol was obtained in 96% yield and 89% e.e. An increase of the size of the 2-substituent had a dramatic effect on enantioselectivity and yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00295-6
• 作为产物：
  描述：

  1,7,7-trimethyl-3-(pyrid-2-ylmethylidene)bicyclo[2.2.1]heptan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以83%的产率得到1,7,7-trimethyl-3-(pyrid-2-ylmethyl)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  (+)-Camphor-derived amino alcohols as ligands for the catalytic enantioselective addition of diethylzinc to benzaldehydes

  摘要：

  1,7,7-Tiimethyl-3-(pyrid-2-ylmethyl) bicyclo[2.2.1]heptan-2-ol 4 and its 2-phenyl, 2-methyl and 2-butyl analogs 5-7 were synthesized, characterized and used as ligands for the addition of diethylzinc to benzaldehydes. Best results were attained with 5 mol% of amino alcohol trans-4 (2-exo,3-endo), in hexane/toluene at rt. Thus, (IS)-1-phenylpropanol was obtained in 96% yield and 89% e.e. An increase of the size of the 2-substituent had a dramatic effect on enantioselectivity and yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00295-6