二环<3.3.0>辛-1(5)-烯-2,6-二酮 | 104266-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 二环<3.3.0>辛-1(5)-烯-2,6-二酮
• 英文名称: bicyclo<3.3.0>oct-1(5)-ene-2,6-dione
• 英文别名: 2,3,5,6-Tetrahydropentalene-1,4-dione；2,3,5,6-tetrahydropentalene-1,4-dione
• CAS: 104266-86-6
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: DDPUSFUAJNOWSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  287.3±10.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二环<3.3.0>辛-1(5)-烯-2,6-二酮 在 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 2,6-二叔丁基-4-甲基吡啶 、 二甲基硫 、 双氧水 、 L-Selectride 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 乙腈 、 苯 为溶剂， 反应 42.55h， 生成 (1R,4R,5S)-4-methoxy-9,12-dioxatricyclo[6.6.0.01,5]tetradec-7-ene
  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 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 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

文献信息

• Cyclopentannulation with a 1,3-dicarbonyl dipole equivalent. Synthesis of bicyclo[3.3.0]oct-1(5)-ene-2,6-dione
  作者：Denis R. St. Laurent、Leo A. Paquette

  DOI：10.1021/jo00370a021

  日期：1986.10
• 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.