ethyl (E)-3-(4-bromobut-3-ynyloxy)acrylate | 1232167-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (E)-3-(4-bromobut-3-ynyloxy)acrylate
• CAS: 1232167-98-4
• 化学式: C₉H₁₁BrO₃
• 分子量: 247.089
• InChiKey: KLRIDGCJKPHTCF-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  ethyl (E)-3-(4-bromobut-3-ynyloxy)acrylate 在 六甲基磷酰三胺 、 samarium diiodide 、 六氟异丙醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以66%的产率得到ethyl (3Z)-{3-(bromomethylene)tetrahydrofuran-2-yl}acetate
  参考文献：
  名称：

  Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters

  摘要：

  An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.

  DOI：

  10.1021/ol101034s
• 作为产物：
  描述：

  ethyl 3-(but-3-yn-1-yloxy)acrylate 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 以91%的产率得到ethyl (E)-3-(4-bromobut-3-ynyloxy)acrylate
  参考文献：
  名称：

  Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters

  摘要：

  An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.

  DOI：

  10.1021/ol101034s