[(5aS,6S,8aS)-8a-hex-5-enyl-2,2-dimethyl-4-oxo-5a,6,7,8-tetrahydro-5H-pentaleno[1,2-d][1,3]dioxin-6-yl] methyl carbonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(5aS,6S,8aS)-8a-hex-5-enyl-2,2-dimethyl-4-oxo-5a,6,7,8-tetrahydro-5H-pentaleno[1,2-d][1,3]dioxin-6-yl] methyl carbonate
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: CZUCPGMVQLMYBG-SIFCLUCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(5aS,6S,8aS)-8a-hex-5-enyl-2,2-dimethyl-4-oxo-5a,6,7,8-tetrahydro-5H-pentaleno[1,2-d][1,3]dioxin-6-yl] methyl carbonate 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 2.5h， 以61%的产率得到
  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 、 氨 、 双氧水 、 乙酸酐 、 lithium 、 三氟乙酸 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 37.33h， 生成 [(5aS,6S,8aS)-8a-hex-5-enyl-2,2-dimethyl-4-oxo-5a,6,7,8-tetrahydro-5H-pentaleno[1,2-d][1,3]dioxin-6-yl] methyl carbonate
  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.