3,4-dibromo-3-methyldihydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,4-dibromo-3-methyldihydrofuran-2-one
• 英文别名: (3R,4R)-3,4-dibromo-3-methyloxolan-2-one
• 化学式: C₅H₆Br₂O₂
• 分子量: 257.909
• InChiKey: YKJURPJTZGVSML-WUJLRWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-3-methyldihydrofuran-2-one 在 lithium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以59%的产率得到(E)-3-bromo-2-buten-1-ol
  参考文献：
  名称：

  A Scalable Route to Trisubstituted (E)-Vinyl Bromides

  摘要：

  An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

  DOI：

  10.1021/ol051376q
• 作为产物：
  描述：

  3-甲基-2(5H)-呋喃酮 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到3,4-dibromo-3-methyldihydrofuran-2-one
  参考文献：
  名称：

  A Scalable Route to Trisubstituted (E)-Vinyl Bromides

  摘要：

  An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

  DOI：

  10.1021/ol051376q

文献信息

• A Scalable Route to Trisubstituted (<i>E</i>)-Vinyl Bromides
  作者：Cheon-Gyu Cho、Won-Suk Kim、Amos B. Smith

  DOI：10.1021/ol051376q

  日期：2005.8.1

  An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.