homogeraniol t-butyldimethylsilyl ether | 162132-02-7

• 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: homogeraniol t-butyldimethylsilyl ether
• 英文别名: 4,8-dimethyl-3(E),7-nonadienyl tert-butyldimethylsilyl ether；tert-butyl-[(3E)-4,8-dimethylnona-3,7-dienoxy]-dimethylsilane
• CAS: 162132-02-7
• 化学式: C₁₇H₃₄OSi
• 分子量: 282.542
• InChiKey: AOVYKAFFRQLCRT-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  homogeraniol t-butyldimethylsilyl ether 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 氨 、 水 、 lithium 、 potassium carbonate 、 苯基锂 、 过碘酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 Toluene-4-sulfonic acid (3E,7E)-10-(5-hydroxy-2-methyl-cyclohex-1-enyl)-4-methyl-deca-3,7-dienyl ester
  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：

  (3Z)-4,8-二甲基-3,7-壬二烯-1-醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以91%的产率得到homogeraniol t-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

• Nucleophilic Phosphine-Catalyzed Iodocyclization of Isoprenoids Bearing an Oxygen Terminal Group
  作者：Kazuaki Ishihara、Akira Sakakura、Gakujun Shomi、Atsushi Ukai

  DOI：10.3987/com-09-s(e)1

  日期：——

  The nucleophilic phosphine-catalyzed diastereoselective iodocyclization of linear isoprenoids bearing an oxygen terminal group was investigated. TBDMS ether of homogeraniol and TBDMS ester of homogeranic acid were successfully converted to the corresponding iodopolycyclic products in the presence of a catalytic amount of triphenylphosphine with complete diastereoselectivity.
• 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.
• Total synthesis of (±)-androst-4-en-3-one-17-carboxylic acid
  作者：Jih Ru Hwu、Eric Jan Leopold

  DOI：10.1039/c39840000721

  日期：——

  The synthesis of the title compound (1) has been accomplished via the polycyclization of epoxide (7d) having an enol acetate as a terminator.

  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。