(3R,5aR,7aS,8S,10aS,10bR)-8-[(5E)-6,10-dimethylundeca-1,5,9-trien-2-yl]-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-3-ol | 1043909-56-3

• 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: (3R,5aR,7aS,8S,10aS,10bR)-8-[(5E)-6,10-dimethylundeca-1,5,9-trien-2-yl]-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-3-ol
• CAS: 1043909-56-3
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: ITLOEEQARWGFHJ-GVZFMBMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,5aR,7aS,8S,10aS,10bR)-8-[(5E)-6,10-dimethylundeca-1,5,9-trien-2-yl]-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-3-ol 在 Oxone 、 Shi's ketone 、 四丁基硫酸氢铵 、 edetate disodium 、 potassium carbonate 作用下， 以 1,2-dimethoxymethane 、 水 、 乙腈 为溶剂， 以37.4%的产率得到(3R,5aR,7aS,8S,10aS,10bR)-8-[4-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]but-1-en-2-yl]-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-3-ol
  参考文献：
  名称：

  Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

  摘要：

  We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

  DOI：

  10.1021/ja1006806
• 作为产物：
  描述：

  (4E)-1-[(3R,5aR,7aR,8R,10aS,10bR)-3-hydroxy-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-8-yl]-5,9-dimethyldeca-4,8-dien-1-one 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.25h， 生成 (3R,5aR,7aS,8S,10aS,10bR)-8-[(5E)-6,10-dimethylundeca-1,5,9-trien-2-yl]-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-3-ol 、 (3R,5aR,7aS,8R,10aS,10bR)-8-[(5E)-6,10-dimethylundeca-1,5,9-trien-2-yl]-4,4,7a,10b-tetramethyl-1,2,3,5a,6,7,8,9,10,10a-decahydroindeno[5,4-b]oxepin-3-ol
  参考文献：
  名称：

  Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

  摘要：

  We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

  DOI：

  10.1021/ja1006806

文献信息

• Mimicking Biosynthesis: Total Synthesis of the Triterpene Natural Product Abudinol B from a Squalene-like Precursor
  作者：Rongbiao Tong、Frank E. McDonald

  DOI：10.1002/anie.200800749

  日期：2008.5.26