4,8,8-trimethylbicyclo[4.4.0]dec-3-en-10-one | 104849-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,8,8-trimethylbicyclo[4.4.0]dec-3-en-10-one
• 英文别名: (4aS,8aS)-3,3,6-trimethyl-2,4,4a,5,8,8a-hexahydronaphthalen-1-one
• CAS: 104849-83-4
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: WQYIPEYEEAHSQO-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  cis-1-bromo-4,8,8-trimethylbicyclo[4.4.0]dec-3-en-10-one 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 三正丁胺 、 二氢吡啶 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到4,8,8-trimethylbicyclo[4.4.0]dec-3-en-10-one
  参考文献：
  名称：

  A Tin-Free Route to trans-Diels–Alder Motifs by Visible Light Photoredox Catalysis

  摘要：

  A tin-free trans-Diels-Alder paradigm for the stereoselective synthesis of trans-fused polycyclic systems was developed through the photocatalytic reductive dehalogenation of alpha-haloketones promoted by visible light. Good to excellent diastereoselectivities were observed in the stereoselective construction of trans-fused octalone derivatives under mild reaction conditions.

  DOI：

  10.1021/acs.joc.5b00041

文献信息

• Diels Alder reactions of cycloalkenones. 11. Regioselectivity of 2-cyclohexenones
  作者：E. Charles Angell、Francesco Fringuelli、Lucio Minuti、Ferdinando Pizzo、Aldo Taticchi、Ernest Wenkert

  DOI：10.1021/jo00376a023

  日期：1986.12
• A Tin-Free Route to <i>trans</i>-Diels–Alder Motifs by Visible Light Photoredox Catalysis
  作者：Jun Hee Lee、Sun-il Mho

  DOI：10.1021/acs.joc.5b00041

  日期：2015.3.20

  A tin-free trans-Diels-Alder paradigm for the stereoselective synthesis of trans-fused polycyclic systems was developed through the photocatalytic reductive dehalogenation of alpha-haloketones promoted by visible light. Good to excellent diastereoselectivities were observed in the stereoselective construction of trans-fused octalone derivatives under mild reaction conditions.