silphinen-3,5-dione

• 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: silphinen-3,5-dione
• 英文别名: (1R,5S,8R,11R)-5,7,7,11-tetramethyltricyclo[6.3.0.01,5]undec-2-ene-4,6-dione
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: YQHSMMDPMZHSTH-QPNXVFALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  柏木脑 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 苯基氯化硒 、 三氟化硼乙醚 、 双氧水 、 sodium acetate 、 potassium hydride 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 二异丙胺 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 61.5h， 生成 silphinen-3,5-dione
  参考文献：
  名称：

  Synthesis of angular triquinanes from (+)-β-cedrol

  摘要：

  Angular triquinanes such as (+)-silphinan-3,5-dione, silphin-3-en-3,5-dione or 2-bromosilphin-3-en-3,5-dione have been obtained from (+)-beta-cedrene in seven steps and an overall yield of 8%. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00928-4

文献信息

• C-5-Substituted Antifeedant Silphinene Sesquiterpenes from <i>Senecio </i><i>p</i><i>almensis</i>
  作者：Matías Reina、Matthias Nold、Omar Santana、Juan Carlos Orihuela、Azucena González-Coloma

  DOI：10.1021/np0105533

  日期：2002.4.1

  The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1), 6,7-epoxy-3(15)-caryophyllene (2), 6,7-epoxy-2,9-humuladiene (3), 5alpha-angeloyloxysilphinen-3-one (4), and 5alpha-acetoxysilphinen-3-one (6) were isolated from bioactive fractions of Senecio palmensis. The structures of these compounds were established by spectroscopic analysis and chemical evidence. The semisynthetic analogues silphinen-3,5-dione (9), 5alpha-hydroxysilphinen-3-one (10), 5beta-hydroxysilphinen-3-one (11), 5beta-acetoxysilphinen-3-one (12), and 5beta-isobutyryloxysilphinen-3-one (13) were generated to carry out a structure-activity study on the antifeedant action of these molecules against several divergent insect species.
• Synthesis of angular triquinanes from (+)-β-cedrol
  作者：Marie-Christine Pierre、Alphonse Tenaglia、Maurice Santelli

  DOI：10.1016/s0040-4020(98)00928-4

  日期：1998.12

  Angular triquinanes such as (+)-silphinan-3,5-dione, silphin-3-en-3,5-dione or 2-bromosilphin-3-en-3,5-dione have been obtained from (+)-beta-cedrene in seven steps and an overall yield of 8%. (C) 1998 Elsevier Science Ltd. All rights reserved.