2,3:18,19-dioxidosqualene

• 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: 2,3:18,19-dioxidosqualene
• 英文别名: 2,2-dimethyl-3-[3,7,12-trimethyl-14-[3-methyl-3-(4-methyl-3-pentenyl)-2-oxiranyl]-(3E,7E,11E)-3,7,11-tetradecatrienyl]oxirane；2,2-dimethyl-3-[(3E,7E,11E)-3,7,12-trimethyl-14-[3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]tetradeca-3,7,11-trienyl]oxirane
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: IEIJIJFCWKQCEX-HAHXBMLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  角鲨烯 在 甲基(三氟甲基)-1,3-二环氧丙烷 、 二甲基二环氧乙烷 作用下， 生成 2,3:18,19-dioxidosqualene
  参考文献：
  名称：

  使用二氧杂环烷直接区域和立体选择性合成角鲨烯2,3; 22,23-二氧化物

  摘要：

  用二甲基二环氧乙烷（1a）及其三氟类似物（1b）选择性地将角鲨烯2,3（S）-氧化物和角鲨烯2,3（R）-氧化物直接转化为相应的2,3（S）； 22（S），23-二氧化物和2,3（R）; 22（R），23-二氧化物。发现这些转化具有方便的区域选择性和非对映选择性，易于获得有价值的二氧化物代谢物。强大的甲基（三氟甲基）二环氧乙烷（1b）是实现目标化合物最佳收率的选择试剂。

  DOI：

  10.1016/j.tetlet.2005.10.022

文献信息

• Dioxidosqualenes: characterization and activity as inhibitors of 2,3-oxidosqualene-lanosterol cyclase
  作者：Jose Luis Abad、Josefina Casas、Francisco Sanchez-Baeza、Angel Messeguer

  DOI：10.1021/jo00067a036

  日期：1993.7

  The preparation and characterization of dioxidosqualenes 4-10 is reported. Treatment of the appropriate epoxysqualene 1, 2, or 3 with NBS followed by chromatographic purification afforded the corresponding epoxybromohydrins 11-14 as diastereomeric mixtures, with the exception of compound 11, which could be separated into the respective racemates 11a and 11b. Further dehydrobromination with NaH in THF led to the respective dioxidosqualenes 4-8 in good conversion yields. Dioxides 9 and 10 were isolated from the crude reaction mixture of the treatment of epoxide 2 with dimethyldioxirane. Characterization of compounds 4-10 was carried out by combining IH and C-13 NMR spectral means with positive GC-MS-CI analysis. The GC-MS-CI analysis included the identification of the carbonyl compounds resulting from the cleavage of dioxido derivatives 4-10 with periodic acid. Finally, data on the activity of dioxidosqualenes as oxidosqualene-lanosterol cyclase (OSLC) inhibitors in rat liver microsomes are also presented. In this respect, 2,3:18,19-dioxidosqualene (7) was found to be the best inhibitor within the compounds assayed (IC50 = 0.11 muM), although dioxides 4, 5, and 9 also exhibited a potent inhibitory activity (IC50 = 21.3, 13.0, and 9.3 muM, respectively). The fact that these compounds could be potentially generated in an organism constitutes a remarkable difference relative to other OSLC inhibitors described to date.
• Direct regio- and stereoselective synthesis of squalene 2,3;22,23-dioxide using dioxiranes
  作者：Lucia D’Accolti、Cosimo Annese、Caterina Fusco

  DOI：10.1016/j.tetlet.2005.10.022

  日期：2005.12

  Dimethyldioxirane (1a) and its trifluoro analog (1b) were employed to achieve selectively the direct transformation of squalene 2,3(S)-oxide and of squalene 2,3(R)-oxide into the corresponding 2,3(S);22(S),23-dioxide and 2,3(R);22(R),23-dioxide, respectively. These transformations were found to occur with convenient regio- and diastereoselectivity, providing easy access to the valuable dioxides metabolites

  用二甲基二环氧乙烷（1a）及其三氟类似物（1b）选择性地将角鲨烯2,3（S）-氧化物和角鲨烯2,3（R）-氧化物直接转化为相应的2,3（S）； 22（S），23-二氧化物和2,3（R）; 22（R），23-二氧化物。发现这些转化具有方便的区域选择性和非对映选择性，易于获得有价值的二氧化物代谢物。强大的甲基（三氟甲基）二环氧乙烷（1b）是实现目标化合物最佳收率的选择试剂。