(1S,3R,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,3'-cyclopentane]-1'-one | 131232-81-0

• 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: (1S,3R,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,3'-cyclopentane]-1'-one
• CAS: 131232-81-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: HACUFGGZRFAFMD-OPQQBVKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,3'-cyclopentane]-1'-one 在 palladium diacetate 、 palladium dichloride 氧气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 90.0~95.0 ℃ 、101.32 kPa 条件下， 反应 14.0h， 以71%的产率得到(1S,3R,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,4'-cyclopent-2-ene]-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：

  2-((1S,2R,4R)-3,3-dimethylbicyclo[2.2.1]heptan-2-yl)acetyl chloride 在 dirhodium tetraacetate 草酰氯 、 水 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 (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

文献信息

• SONAWANE, HARIKISAN R.;BELLUR, NAJIUNDIAH S.;AHUJA, JAIMALA R.;KULKARNI, +, J. ORG. CHEM., 56,(1991) N, C. 1434-1439
  作者：SONAWANE, HARIKISAN R.、BELLUR, NAJIUNDIAH S.、AHUJA, JAIMALA R.、KULKARNI, +

  DOI：——

  日期：——