(1R,4R)-2-benzyl-5-trifluoromethanesulfonyloxybicyclo[2.2.1]hepta-2,5-diene | 608489-12-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (1R,4R)-2-benzyl-5-trifluoromethanesulfonyloxybicyclo[2.2.1]hepta-2,5-diene
• 英文别名: [(1R,4R)-5-benzyl-2-bicyclo[2.2.1]hepta-2,5-dienyl] trifluoromethanesulfonate
• CAS: 608489-12-9
• 化学式: C₁₅H₁₃F₃O₃S
• 分子量: 330.328
• InChiKey: ABDJNHWEVKAHMO-OLZOCXBDSA-N

物化性质

• 沸点：
  402.6±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苄基溴化镁 、 (1R,4R)-2-benzyl-5-trifluoromethanesulfonyloxybicyclo[2.2.1]hepta-2,5-diene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 乙醚 为溶剂， 以45%的产率得到(R,R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene
  参考文献：
  名称：

  A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts:  Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-Addition

  摘要：

  As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to alpha,beta-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.

  DOI：

  10.1021/ja037367z
• 作为产物：
  描述：

  (,)-双环[2.2.1]庚烷-2,5-二酮 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 (1R,4R)-2-benzyl-5-trifluoromethanesulfonyloxybicyclo[2.2.1]hepta-2,5-diene
  参考文献：
  名称：

  A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts:  Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-Addition

  摘要：

  As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to alpha,beta-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.

  DOI：

  10.1021/ja037367z

文献信息

• A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts:  Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-Addition
  作者：Tamio Hayashi、Kazuhito Ueyama、Norihito Tokunaga、Kazuhiro Yoshida

  DOI：10.1021/ja037367z

  日期：2003.9.1

  As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to alpha,beta-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.