| 55786-46-4

• 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
• CAS: 55786-46-4；55786-47-5
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: CAXDZYWRFVOOSC-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 月桂烯 以 xylene 为溶剂， 生成
  参考文献：
  名称：

  De Smet,A. et al., Bulletin des Societes Chimiques Belges, 1975, vol. 84, p. 67 - 75

  摘要：

  DOI：

文献信息

• Access to Optically Active 7-Membered Rings by a 2-Step Synthetic Sequence: Cu-Catalyzed Stereoselective Cyclopropanation of Branched 1,3-Dienes/Rh-Catalyzed Stereoconvergent [5 + 2] Cycloaddition
  作者：Michele Garbo、Céline Besnard、Laure Guénée、Clément Mazet

  DOI：10.1021/acscatal.0c02956

  日期：2020.8.21

  We report a 2-step cyclopropanation/cycloaddition catalytic sequence that provides access to optically active 7-membered rings with a carboxyl-bearing tertiary stereocenter. In the first step, the Cu-catalyzed cyclopropanation of branched dienes generates vinylcyclopropanes in high yields, regioselectivity and enantioselectivity, albeit in modest cis/trans diastereoselectivity. The stereoconvergent nature of the subsequent Rh-catalyzed [5 + 2] cycloaddition with alkynes overrides this apparent limitation and affords preferentially one 7-membered ring out of the 8 or 16 possible stereoisomers that can be theoretically generated. The final regioselectivity and enantioselectivity are high in the majority of cases . The method is versatile and tolerates a broad range of functional groups.