2-[(1S)-4-methylcyclohexa-2,4-dien-1-yl]propanoic acid | 208336-25-8

• 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: 2-[(1S)-4-methylcyclohexa-2,4-dien-1-yl]propanoic acid
• CAS: 208336-25-8
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ZPSLHALRDVIKTA-YGPZHTELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1S)-4-methylcyclohexa-2,4-dien-1-yl]propanoic acid 在 palladium diacetate 氧气 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 58.0h， 生成 (3R,3aR,5R,7aS)-5-hydroxy-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one
  参考文献：
  名称：

  Enantiocontrolled Formal Total Synthesis of Paeonilactone A and B from (S)-(+)-Carvone.

  摘要：

  A synthesis of enantiomerically pure lactone 11a from commercially available (S)-(+)-carvone has been developed. The synthesis constitutes a formal synthesis of paeonilactone A and B and involves a stereoselective palladium-catalyzed 1,4-oxylactonization of a conjugated diene to introduce two of the oxygen substituents required for the target.

  DOI：

  10.3891/acta.chem.scand.52-0524
• 作为产物：
  描述：

  (4S)-p-mentha-1,5-dien-9-ol 在 氢氧化钾 、 草酰氯 、 silver nitrate 、 二甲基亚砜 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成 2-[(1S)-4-methylcyclohexa-2,4-dien-1-yl]propanoic acid
  参考文献：
  名称：

  Enantiocontrolled Formal Total Synthesis of Paeonilactone A and B from (S)-(+)-Carvone.

  摘要：

  A synthesis of enantiomerically pure lactone 11a from commercially available (S)-(+)-carvone has been developed. The synthesis constitutes a formal synthesis of paeonilactone A and B and involves a stereoselective palladium-catalyzed 1,4-oxylactonization of a conjugated diene to introduce two of the oxygen substituents required for the target.

  DOI：

  10.3891/acta.chem.scand.52-0524

文献信息

• Enantiocontrolled Formal Total Synthesis of Paeonilactone A and B from (S)-(+)-Carvone.
  作者：Magnus Rönn、Pher G. Andersson、Jan-E. Bäckvall、Olle Matsson、Jadwiga Trocha-Grimshaw、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0524

  日期：——

  A synthesis of enantiomerically pure lactone 11a from commercially available (S)-(+)-carvone has been developed. The synthesis constitutes a formal synthesis of paeonilactone A and B and involves a stereoselective palladium-catalyzed 1,4-oxylactonization of a conjugated diene to introduce two of the oxygen substituents required for the target.