(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester | 886580-13-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester
• CAS: 886580-13-8
• 化学式: C₁₇H₂₆O₃Si
• 分子量: 306.477
• InChiKey: CZEFNTRERUEOQI-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester 在 溴 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 (E)-2-bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-but-2-en-1-ol
  参考文献：
  名称：

  Synthesis and DNA cleavage reaction characteristics of enediyne prodrugs activated via an allylic rearrangement by base or UV irradiation

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.12.040
• 作为产物：
  描述：

  三甲基膦酰基乙酸酯 、 乙酮,2-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-1-苯基- 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 以60%的产率得到(Z)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis and DNA cleavage reaction characteristics of enediyne prodrugs activated via an allylic rearrangement by base or UV irradiation

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.12.040