(1R,4R)-spiro[5-benzylbicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane] | 608489-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4R)-spiro[5-benzylbicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]
• 英文别名: (1'R,4'R)-2'-benzylspiro[1,3-dioxolane-2,5'-bicyclo[2.2.1]hept-2-ene]
• CAS: 608489-10-7
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: AEHRBHWWJLJCMS-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4R)-spiro[5-benzylbicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane] 在 盐酸 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 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
• 作为产物：
  描述：

  (,)-双环[2.2.1]庚烷-2,5-二酮 在 (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)-spiro[5-benzylbicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]
  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.