(E)-4-(tert-butyldimethylsilanyloxy)-2-fluoro-3-methyl-but-2-enoic acid ethyl ester | 940003-83-8

• 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: (E)-4-(tert-butyldimethylsilanyloxy)-2-fluoro-3-methyl-but-2-enoic acid ethyl ester
• 英文别名: (E)-2-fluoro-4-(tert-butyldimethylsilyloxy)-3-methyl-but-2-enoic acid ethyl ester；ethyl (E)-4-[tert-butyl(dimethyl)silyl]oxy-2-fluoro-3-methylbut-2-enoate
• CAS: 940003-83-8
• 化学式: C₁₃H₂₅FO₃Si
• 分子量: 276.424
• InChiKey: HWEBRMVTSFRIBA-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(tert-butyldimethylsilanyloxy)-2-fluoro-3-methyl-but-2-enoic acid ethyl ester 在 diethylzinc 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (+/-)-[2-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-fluorocyclopropyl]-methanol
  参考文献：
  名称：

  Synthesis and antiviral activity of C-fluoro-branched cyclopropyl nucleosides

  摘要：

  A series of novel fluorocyclopropyl nucleosides were synthesized starting from acetol using the Simmons-Smith reaction as a key reaction. All the nucleosides synthesized were assayed against several viruses. Among the compounds synthesized, the uracil analogue 22 showed moderate anti-HCMV activity (10.61 mu g/mL, in AD-169). (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.11.002
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 1-(叔丁基二甲基硅氧基)-2-丙酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 六甲基磷酰三胺 为溶剂， 以51%的产率得到(E)-4-(tert-butyldimethylsilanyloxy)-2-fluoro-3-methyl-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Selective Synthesis and Application to the Synthesis of (E)-Fluorovinyl Nucleosides

  摘要：

  A selective method for synthesizing (E)fluorovinyl was developed. Novel acyclic (E)-fluorovinyl versions of neplanocin A were designed and selectively synthesized as potential antiviral agents. The condensation of the bromide 7 with the nucleosidic bases (5-FU, C, A, G) and the deprotection afforded the desired acyclic fluorovinyl nucleosides. The synthesized compounds 11, 12, 13, and 16 were evaluated for their antiviral activity. The guanine derivative 16 showed toxicity-dependent anti-HIV-1 activity in MT-4 cells.

  DOI：

  10.1080/15257770701845170