Methanesulfonic acid (E)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl ester | 1071009-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (E)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl ester
• CAS: 1071009-59-0
• 化学式: C₁₄H₃₀O₄SSi
• 分子量: 322.541
• InChiKey: RYBAJPBXCKAPPZ-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (E)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl ester 在 正丁基锂 、 lithium chloride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 3.75h， 生成 tert-butyl(((4E,8E)-11-((R)-6-(methoxymethoxy)-2,8-dimethylchroman-2-yl)-4,8-dimethyl-7-(phenylsulfonyl)undeca-4,8-dien-1-yl)oxy)dimethylsilane
  参考文献：
  名称：

  氟代δ-生育三烯酚衍生物的合成及其肝微粒体代谢稳定性研究。

  摘要：

  合成了氟取代的δ-生育三烯酚衍生物DT3-F2。该化合物被设计为通过用CF键取代两个甲基上每个的一个CH键来稳定δ-生育三烯酚的代谢不稳定的甲基。但是，使用小鼠肝微粒体进行的体外代谢稳定性研究表明，DT3-F2发生了意外的快速酶促CF键水解。据我们所知，这是烯丙基CF键异常代谢水解的第一个报道。

  DOI：

  10.1002/cmdc.201900676
• 作为产物：
  描述：

  (E)-tert-butyl((5-iodo-4-methylpent-4-en-1-yl)oxy)dimethylsilane 在 正丁基锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 生成 Methanesulfonic acid (E)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl ester
  参考文献：
  名称：

  Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.

  DOI：

  10.1021/ja00107a011