6-(benzylamino)-5-methyl-5-(4-methylphenyl)bicyclo[2.2.2]octan-2-one | 1236831-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(benzylamino)-5-methyl-5-(4-methylphenyl)bicyclo[2.2.2]octan-2-one
• 英文别名: 6-(benzylamino)-5-methyl-5-(4-methylphenyl)-bicyclo[2.2.2]octan-2-one；(1S,4S,5R,6S)-6-(benzylamino)-5-methyl-5-(4-methylphenyl)bicyclo[2.2.2]octan-2-one
• CAS: 1236831-90-5
• 化学式: C₂₃H₂₇NO
• 分子量: 333.473
• InChiKey: AXYVBVZCPGZMDZ-MQFRRQCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 2-(对甲苯基)丙醛 、 苄胺 在 (S)-N-(4-十二烷基苯磺酰基)吡咯烷-2-甲酰胺 作用下， 以 甲苯 为溶剂， 反应 72.5h， 生成 6-(benzylamino)-5-methyl-5-(4-methylphenyl)bicyclo[2.2.2]octan-2-one 、 6-(benzylamino)-5-methyl-5-(4-methylphenyl)bicyclo[2.2.2]octan-2-one
  参考文献：
  名称：

  Organocatalyzed, enantioselective synthesis of bicyclo-[2.2.2]-octanes containing benzylic, all-carbon quaternary centers

  摘要：

  Proline aryl sulfonamide-catalyzed, multi-component couplings have been developed for accessing densely functionalized [2.2.2] bicyclic ketones containing up to four contiguous chiral centers including an all-carbon benzylic quaternary center in high enantio- and diastereoselectivity. Application to the bicyclic core of the recently isolated alkaloid kopsonoline is illustrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.094

文献信息

• Organocatalyzed, enantioselective synthesis of bicyclo-[2.2.2]-octanes containing benzylic, all-carbon quaternary centers
  作者：Hua Yang、Rich G. Carter

  DOI：10.1016/j.tet.2010.01.094

  日期：2010.6

  Proline aryl sulfonamide-catalyzed, multi-component couplings have been developed for accessing densely functionalized [2.2.2] bicyclic ketones containing up to four contiguous chiral centers including an all-carbon benzylic quaternary center in high enantio- and diastereoselectivity. Application to the bicyclic core of the recently isolated alkaloid kopsonoline is illustrated. (C) 2010 Elsevier Ltd. All rights reserved.