(E)-2-bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-but-2-en-1-ol | 736156-58-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-2-bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-but-2-en-1-ol
• 英文别名: (E)-2-bromo-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-en-1-ol
• CAS: 736156-58-4
• 化学式: C₁₆H₂₅BrO₂Si
• 分子量: 357.363
• InChiKey: KPELPESUFLHFEF-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (E)-2-bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-but-2-en-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-1-[2-bromo-4-(tert-butyldimethylsilanyloxy)-3-phenyl-but-2-enyl]-5-iodouracil
  参考文献：
  名称：

  Simple Synthesis of Novel Acyclic (E)-Bromovinyl Nucleosides as Potential Antiviral Agents

  摘要：

  In these study, novel acyclic ( E )-bromovinyl nucleosides were synthesized as potential antiviral agents. The coupling of the allylic bromide 9 with bases (thymine, uracil, 5-fluorouracul, 5-iodouracil, cytosine, adenine) afforded a series of novel acyclic nucleosides. The synthesized compounds were evaluated for their antiviral activity against various viruses such as HIV-1, HSV-1, HSV-2, and HCMV. 5-Iodouracil analogue 19 showed weak anti-HIV-1 activity.

  DOI：

  10.1080/15257770600793877
• 作为产物：
  描述：

  (Z)-4-(t-butyldimethylsilyloxy)-3-phenyl-but-2-enoic acid ethyl ester 在 溴 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 作用下， 以 四氯化碳 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (E)-2-bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-but-2-en-1-ol
  参考文献：
  名称：

  Simple Synthesis of Novel Acyclic (E)-Bromovinyl Nucleosides as Potential Antiviral Agents

  摘要：

  In these study, novel acyclic ( E )-bromovinyl nucleosides were synthesized as potential antiviral agents. The coupling of the allylic bromide 9 with bases (thymine, uracil, 5-fluorouracul, 5-iodouracil, cytosine, adenine) afforded a series of novel acyclic nucleosides. The synthesized compounds were evaluated for their antiviral activity against various viruses such as HIV-1, HSV-1, HSV-2, and HCMV. 5-Iodouracil analogue 19 showed weak anti-HIV-1 activity.

  DOI：

  10.1080/15257770600793877

文献信息

• Synthesis and DNA cleavage reaction characteristics of enediyne prodrugs activated via an allylic rearrangement by base or UV irradiation
  作者：Yukihiro Tachi、Wei-Min Dai、Kazuhito Tanabe、Sei-ichi Nishimoto

  DOI：10.1016/j.bmc.2005.12.040

  日期：2006.5

  A number of enediyne prodrugs 1-5 possessing in (E)-3-Ilydi-oxy-4-(2'-hydroxy-1'-phenylethylidene)cyclodeca-1,5-diyne scaffold have been synthesized via the Sonogashira Coupling and an intramolecular Nozaki-Hiyama-Kishi reaction as the key steps. Upon incubation with enediyne prodrugs 4 and 5 possessing a free hydroxymethyl group oil the exocyclic double bond, circular supercoiled DNA (Form 1) underwent single strand cleavage into Circular relaxed DNA (Form 11) in buffer solution at pH 8.5, while the silylated analogs 1-3 showed very weak DNA cleavage activity. Alternatively, the silylated analogs 1-3 Could be activated by UV irradiation via a photochemical alkene isomerization followed by an allylic rearrangement to form the putative epoxy enediyne, resulting in efficient DNA cleavage similar to the level observed with the prodrugs 4 and 5. (c) 2005 Elsevier Ltd. All rights reserved.