methyl 3-acetoxy-3-[(2-benzyloxy-5-bromophenyl)-2-methylene]propanoate | 1101179-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-acetoxy-3-[(2-benzyloxy-5-bromophenyl)-2-methylene]propanoate
• 英文别名: methyl 3-acetoxy-3-(2-benzyloxy-5-bromo)phenyl-2-methylenepropanoate；Methyl 2-[acetyloxy-(5-bromo-2-phenylmethoxyphenyl)methyl]prop-2-enoate
• CAS: 1101179-86-5
• 化学式: C₂₀H₁₉BrO₅
• 分子量: 419.272
• InChiKey: UEUPHKYOTSRFGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-acetoxy-3-[(2-benzyloxy-5-bromophenyl)-2-methylene]propanoate 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 36.0h， 生成 methyl (E)-3-(2-benzyloxy-5-bromo-phenyl)-2-[[[1-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl]triazol-4-yl]methylamino]methyl]prop-2-enoate
  参考文献：
  名称：

  Synthesis of cinnamate ester–AZT conjugates as potential dual-action HIV-1 integrase and reverse transcriptase inhibitors

  摘要：

  Synthetic approaches to a series of novel cinnamate ester-AZT conjugates have been explored and a successful pathway has finally been developed. alpha-(Halomethyl)cinnamate esters, obtained in high yield by treating benzyl-protected salicylaldehde-derived Baylis-Hillman adducts with acetyl bromide at low temperature, have been treated with propargylamine to afford substrates for click chemistry reactions with azidothymidine (AZT) in the presence of in situ generated Cu(I) catalyst to produce the title compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.045
• 作为产物：
  描述：

  2-苄氧基-5-溴苯甲醛 在 吡啶 、 三乙烯二胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 504.0h， 生成 methyl 3-acetoxy-3-[(2-benzyloxy-5-bromophenyl)-2-methylene]propanoate
  参考文献：
  名称：

  Synthesis of cinnamate ester–AZT conjugates as potential dual-action HIV-1 integrase and reverse transcriptase inhibitors

  摘要：

  Synthetic approaches to a series of novel cinnamate ester-AZT conjugates have been explored and a successful pathway has finally been developed. alpha-(Halomethyl)cinnamate esters, obtained in high yield by treating benzyl-protected salicylaldehde-derived Baylis-Hillman adducts with acetyl bromide at low temperature, have been treated with propargylamine to afford substrates for click chemistry reactions with azidothymidine (AZT) in the presence of in situ generated Cu(I) catalyst to produce the title compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.045

文献信息

• Application of the acetate of baylis-hillman adducts of salicylaldehydes in the synthesis of methyl 2-oxo-2,3-dihydrobenzo[<i>b</i>]oxepine-4-carboxylates
  作者：Sang-Hyun Ahn、Hee Nam Lim、Kee-Jung Lee

  DOI：10.1002/jhet.5570450622

  日期：2008.11

  A simple synthesis of several methyl 2-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates from Baylis-Hillman adducts of O-benzyl protected 2-hydroxybenzadehydes has been described through the acetylation, cyanation, debenzylation, as well as acid assisted Pinner cyclization.

  已经描述了通过乙酰化，氰化，脱苄基以及O-苄基保护的2-羟基苯甲醛的Baylis-Hillman加合物简单合成几种2-oxo-2,3-dihydrobenzo [ b ] oxepine-4-羧酸甲酯的方法。酸辅助的Pinner环化。