1-diazo-4-[(1S,2R,4R)-3,3-dimethyl-2-bicyclo[2.2.1]heptanyl]butan-2-one | 131131-46-9

• 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
• 英文名称: 1-diazo-4-[(1S,2R,4R)-3,3-dimethyl-2-bicyclo[2.2.1]heptanyl]butan-2-one
• CAS: 131131-46-9
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: SYKVRPKOKXVDML-HOSYDEDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-diazo-4-[(1S,2R,4R)-3,3-dimethyl-2-bicyclo[2.2.1]heptanyl]butan-2-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到(1S,3R,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,3'-cyclopentane]-1'-one
  参考文献：
  名称：

  Site-selective rhodium(II) acetate mediated intramolecular metal-carbene insertions into carbon-hydrogen bonds of bicyclo[2.2.1]heptanes: effcient syntheses of (+)-albene and (-)-.beta.-santalene

  摘要：

  Treatment of alpha-diazo ketones 1a-d and 2a-d with catalytic amounts of rhodium(II) acetate led to selective carbene insertions into C-H bonds resulting in cyclopentane-annulated products in high yields. The highly selective insertion realized into the exo-methyl C-H bond of 1a has been utilized in the syntheses of (+)-albene (8) and (-)-beta-santalene (11).

  DOI：

  10.1021/jo00004a019
• 作为产物：
  描述：

  Isocamphenilanylessigsaeure 在 草酰氯 、 水 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 为溶剂， 反应 28.0h， 生成 1-diazo-4-[(1S,2R,4R)-3,3-dimethyl-2-bicyclo[2.2.1]heptanyl]butan-2-one
  参考文献：
  名称：

  Site-selective rhodium(II) acetate mediated intramolecular metal-carbene insertions into carbon-hydrogen bonds of bicyclo[2.2.1]heptanes: effcient syntheses of (+)-albene and (-)-.beta.-santalene

  摘要：

  Treatment of alpha-diazo ketones 1a-d and 2a-d with catalytic amounts of rhodium(II) acetate led to selective carbene insertions into C-H bonds resulting in cyclopentane-annulated products in high yields. The highly selective insertion realized into the exo-methyl C-H bond of 1a has been utilized in the syntheses of (+)-albene (8) and (-)-beta-santalene (11).

  DOI：

  10.1021/jo00004a019

文献信息

• Site-selective rhodium(II) acetate mediated intramolecular metal-carbene insertions into carbon-hydrogen bonds of bicyclo[2.2.1]heptanes: effcient syntheses of (+)-albene and (-)-.beta.-santalene
  作者：Harikisan R. Sonawane、Nanjundiah S. Bellur、Jaimala R. Ahuja、Dilip G. Kulkarni

  DOI：10.1021/jo00004a019

  日期：1991.2

  Treatment of alpha-diazo ketones 1a-d and 2a-d with catalytic amounts of rhodium(II) acetate led to selective carbene insertions into C-H bonds resulting in cyclopentane-annulated products in high yields. The highly selective insertion realized into the exo-methyl C-H bond of 1a has been utilized in the syntheses of (+)-albene (8) and (-)-beta-santalene (11).