(E)-ethyl 4-(tert-butyldiphenylsilanyloxy)-2-fluoro-2-butenol | 186953-21-9

• 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: (E)-ethyl 4-(tert-butyldiphenylsilanyloxy)-2-fluoro-2-butenol
• 英文别名: (E)-4-[tert-butyl(diphenyl)silyl]oxy-2-fluorobut-2-en-1-ol
• CAS: 186953-21-9
• 化学式: C₂₀H₂₅FO₂Si
• 分子量: 344.501
• InChiKey: AHILSSOBRWGUOF-SAPNQHFASA-N

物化性质

• 沸点：
  407.3±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(tert-butyldiphenylsilanyloxy)-2-fluoro-2-butenol 在 吡啶 、 diethylzinc 、 sodium hydride 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  DESIGN AND SYNTHESIS OF NOVEL FLUOROCYCLOPROPANOID NUCLEOSIDES

  摘要：

  Novel fluorocyclopropanoid nucleosides were designed, synthesized and evaluated their antiviral activities against poliovirus, HSV, HIV, and HBV.

  DOI：

  10.1081/ncn-100002349
• 作为产物：
  描述：

  叔丁基二苯基硅烷 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 (E)-ethyl 4-(tert-butyldiphenylsilanyloxy)-2-fluoro-2-butenol
  参考文献：
  名称：

  Synthesis of Retinals Fluorinated at Odd-Numbered Side-Chain Positions and of the Corresponding Fluorobacteriorhodopsins

  摘要：

  Conventional Horner-Wadsworth-Emmons and Wittig condensations were used to fluorinate the odd-numbered positions of the retinal side chain past C-7. The stereochemically labile cis-fluororetinals were easily converted into the most stable trans-flouretinals, which were incubated with bacterio-opsin. Contrary to expectations, the fluorinated retinals provided artificial pigments with near normal absorption properties, showing that any electrostatic interactions between the fluorine atoms and protein groups were insufficient to prevent normal binding. The new artificial pigments had smaller opsin shifts than did native bacteriorhodopsin, which is interpreted as due either to greater electrostatic interaction between the protonated imine and its counterion, or to local interactions between the fluorine substituents and nearby polar protein groups.

  DOI：

  10.1021/jo961355x

文献信息

• Inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and VAP-1 mediated adhesion useful for treatment and prevention of diseases
  申请人：Wang Yanjun Eric

  公开号：US20070293548A1

  公开（公告）日：2007-12-20

  Compositions and methods of using compositions for treatment of inflammatory diseases and immune disorders are provided. Allylamino compounds are disclosed which are inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and/or vascular adhesion protein 1 (VAP-1). The compounds have therapeutic utility in suppressing inflammation and inflammatory responses, and in treatment of several disorders, including multiple sclerosis and stroke.

  提供了用于治疗炎症性疾病和免疫紊乱的组合物及使用组合物的方法。公开了一种烯丙胺化合物，它们是半胱氨酸敏感胺氧化酶（SSAO）和/或血管粘附蛋白1（VAP-1）的抑制剂。这些化合物在抑制炎症和炎症反应方面具有治疗效用，并可用于治疗多发性硬化症和中风等多种疾病。
• DESIGN AND SYNTHESIS OF NOVEL FLUOROCYCLOPROPANOID NUCLEOSIDES
  作者：Young Rang Lee、Ju-Hyun Park、Raok Jeon、Lak Shin Jeong、Moon Woo Chun、Hee-Doo Kim

  DOI：10.1081/ncn-100002349

  日期：2001.3.31

  Novel fluorocyclopropanoid nucleosides were designed, synthesized and evaluated their antiviral activities against poliovirus, HSV, HIV, and HBV.
• Synthesis of Retinals Fluorinated at Odd-Numbered Side-Chain Positions and of the Corresponding Fluorobacteriorhodopsins
  作者：Andrés Francesch、Rosana Alvarez、Susana López、Angel R. de Lera

  DOI：10.1021/jo961355x

  日期：1997.1.1

  Conventional Horner-Wadsworth-Emmons and Wittig condensations were used to fluorinate the odd-numbered positions of the retinal side chain past C-7. The stereochemically labile cis-fluororetinals were easily converted into the most stable trans-flouretinals, which were incubated with bacterio-opsin. Contrary to expectations, the fluorinated retinals provided artificial pigments with near normal absorption properties, showing that any electrostatic interactions between the fluorine atoms and protein groups were insufficient to prevent normal binding. The new artificial pigments had smaller opsin shifts than did native bacteriorhodopsin, which is interpreted as due either to greater electrostatic interaction between the protonated imine and its counterion, or to local interactions between the fluorine substituents and nearby polar protein groups.