4-Hydroxy-3,4,5,6-tetrahydro-2H-pentalen-1-one | 162281-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-3,4,5,6-tetrahydro-2H-pentalen-1-one
• CAS: 162281-90-5
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: BUWYXRHIMWJZMG-UHFFFAOYSA-N

物化性质

• 沸点：
  318.6±21.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  4-Hydroxy-3,4,5,6-tetrahydro-2H-pentalen-1-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到二环<3.3.0>辛-1(5)-烯-2,6-二酮
  参考文献：
  名称：

  Inside-outside stereoisomerism. VII. Methodology for the Synthesis of 3-Oxygenated Ingenanes. The First Ingenol Analogs with High Affinity for Protein Kinase C

  摘要：

  Previous work from our laboratories has demonstrated that the intramolecular dioxenone photocycloaddition reaction leads to a stereoselective synthesis of the carbocyclic ring system of the ingenane diterpenes with the ''inside-outside'' stereochemical relationship that is required for biological activity. Two different approaches for the synthesis of C-3 oxygenated analogs of ingenol and the preparation of the first ingenane analog with high affinity for protein kinase C are described.

  DOI：

  10.1021/jo00110a048
• 作为产物：
  描述：

  3,4,5,6-tetrahydro-2H-pentalen-1-one 在 sodium hydroxide 、 高氯酸 、 双氧水 作用下， 生成 4-Hydroxy-3,4,5,6-tetrahydro-2H-pentalen-1-one
  参考文献：
  名称：

  Inside-outside stereoisomerism. VII. Methodology for the Synthesis of 3-Oxygenated Ingenanes. The First Ingenol Analogs with High Affinity for Protein Kinase C

  摘要：

  Previous work from our laboratories has demonstrated that the intramolecular dioxenone photocycloaddition reaction leads to a stereoselective synthesis of the carbocyclic ring system of the ingenane diterpenes with the ''inside-outside'' stereochemical relationship that is required for biological activity. Two different approaches for the synthesis of C-3 oxygenated analogs of ingenol and the preparation of the first ingenane analog with high affinity for protein kinase C are described.

  DOI：

  10.1021/jo00110a048

文献信息

• Inside-outside stereoisomerism. VII. Methodology for the Synthesis of 3-Oxygenated Ingenanes. The First Ingenol Analogs with High Affinity for Protein Kinase C
  作者：Jeffrey D. Winkler、Bor-Cherng Hong、Afshin Bahador、Marcelo G. Kazanietz、Peter M. Blumberg

  DOI：10.1021/jo00110a048

  日期：1995.3

  Previous work from our laboratories has demonstrated that the intramolecular dioxenone photocycloaddition reaction leads to a stereoselective synthesis of the carbocyclic ring system of the ingenane diterpenes with the ''inside-outside'' stereochemical relationship that is required for biological activity. Two different approaches for the synthesis of C-3 oxygenated analogs of ingenol and the preparation of the first ingenane analog with high affinity for protein kinase C are described.