Pseudopterosin F | 124645-98-3

• 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: Pseudopterosin F
• 英文别名: (2R,3R,4S,5S)-2-[[(4R,6S,6aR,9S)-1-hydroxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-2-yl]oxy]oxane-3,4,5-triol
• CAS: 124645-98-3
• 化学式: C₂₅H₃₆O₆
• 分子量: 432.557
• InChiKey: MWZXYPPIOWWIFA-PMMNNFIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Pseudopterosin F 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 (4R,6S,6aR,9S)-1-Methoxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-2-ol
  参考文献：
  名称：

  New anti-inflammatory pseudopterosins from the marine octocoral Pseudopterogorgia elisabethae

  摘要：

  DOI：

  10.1021/jo00303a030
• 作为产物：
  描述：

  amphilectosin B 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以87%的产率得到Pseudopterosin F
  参考文献：
  名称：

  Identification of Amphilectosins as Key Intermediates in Pseudopterosin Biosynthesis

  摘要：

  Amphilectosins A and B have been identified from the organic extract of Pseudopterogorgia elisabethae collected in the Florida Keys, along with seco-pseudopterosins and pseudopterosins. The structures of the amphilectosins, "C-12-C-13 dehydro seco-pseudopterosins", suggested that these metabolites provide the biosynthetic link between the seco-pseudopterosins (serrulatane diterpenes) and pseudopterosins (amphilectane diterpenes). This biosynthetic relationship was confirmed through various radiolabeling experiments. Incubation studies with the amphilectosins revealed the selective transformation of amphilectosin A to pseudopterosin Y and the transformation of amphilectosin B to pseudopterosin F, which suggests that alpha/beta stereochemistry for the isobutenyl group in the pseudopterosins arises from the selective ring closure of the cis- and transamphilectosins.

  DOI：

  10.1021/jo050282r

文献信息

• New anti-inflammatory pseudopterosins from the marine octocoral Pseudopterogorgia elisabethae
  作者：Vassilios Roussis、Zhongde Wu、William Fenical、Scott A. Strobel、Gregory D. Van Duyne、Jon Clardy

  DOI：10.1021/jo00303a030

  日期：1990.8
• Identification of Amphilectosins as Key Intermediates in Pseudopterosin Biosynthesis
  作者：Tyrone A. Ferns、Russell G. Kerr

  DOI：10.1021/jo050282r

  日期：2005.8.1

  Amphilectosins A and B have been identified from the organic extract of Pseudopterogorgia elisabethae collected in the Florida Keys, along with seco-pseudopterosins and pseudopterosins. The structures of the amphilectosins, "C-12-C-13 dehydro seco-pseudopterosins", suggested that these metabolites provide the biosynthetic link between the seco-pseudopterosins (serrulatane diterpenes) and pseudopterosins (amphilectane diterpenes). This biosynthetic relationship was confirmed through various radiolabeling experiments. Incubation studies with the amphilectosins revealed the selective transformation of amphilectosin A to pseudopterosin Y and the transformation of amphilectosin B to pseudopterosin F, which suggests that alpha/beta stereochemistry for the isobutenyl group in the pseudopterosins arises from the selective ring closure of the cis- and transamphilectosins.