7-bromo-8-hydroxy-4,8-dimethyl-3(E)-nonenyl tert-butyldimethylsilyl ether | 162132-03-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 7-bromo-8-hydroxy-4,8-dimethyl-3(E)-nonenyl tert-butyldimethylsilyl ether
• CAS: 162132-03-8
• 化学式: C₁₇H₃₅BrO₂Si
• 分子量: 379.453
• InChiKey: DVPAFHPYLQHOIP-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-bromo-8-hydroxy-4,8-dimethyl-3(E)-nonenyl tert-butyldimethylsilyl ether 在 potassium carbonate 、 过碘酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 (4E)-4-methyl-7-(1,1,2,2-tetramethyl-1-silapropoxy)hept-4-enal
  参考文献：
  名称：

  （±）-androst-4-en-3-one-17-羧酸的全合成

  摘要：

  标题化合物（1）的合成已经通过具有烯醇乙酸酯作为终止剂的环氧化物（7d）的多环化而完成。

  DOI：

  10.1039/c39840000721
• 作为产物：
  描述：

  homogeraniol t-butyldimethylsilyl ether 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以66%的产率得到7-bromo-8-hydroxy-4,8-dimethyl-3(E)-nonenyl tert-butyldimethylsilyl ether
  参考文献：
  名称：

  （±）-androst-4-en-3-one-17-羧酸的全合成

  摘要：

  标题化合物（1）的合成已经通过具有烯醇乙酸酯作为终止剂的环氧化物（7d）的多环化而完成。

  DOI：

  10.1039/c39840000721

文献信息

• Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Nafsika H. Georgopapadakou、Peter G. Hartman、Petra Scheliga

  DOI：10.1021/ja00107a011

  日期：1995.1

  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.