5-bromo-4-phenyl-2(5H)-furanone | 1575-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-bromo-4-phenyl-2(5H)-furanone
• 英文别名: 4-Brom-3-phenyl-buten-(2)-olid；2-bromo-3-phenyl-2H-furan-5-one
• CAS: 1575-55-9
• 化学式: C₁₀H₇BrO₂
• 分子量: 239.068
• InChiKey: SGWUWILUMDUZLS-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  369.2±42.0 °C(Predicted)
• 密度：
  1.636±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  5-bromo-4-phenyl-2(5H)-furanone 、 3-oxo-2-phthalimido-propionic acid methyl ester 在 potassium tert-butylate 作用下， 生成 methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(3-phenyl-5-oxo-2,5-dihydrofuran-2-yloxy)acrylate
  参考文献：
  名称：

  N-Phthaloylglycine-Derived Strigol Analogues. Influence of the D-Ring on Seed Germination Activity of the Parasitic Weeds Striga hermonthica and Orobanche crenata

  摘要：

  Several strigol analogues with modifications in the D-ring were synthesized and assayed for germination stimulatory activity of seeds of Striga hermonthica and Orobanche crenata. All of these D-ring analogues are derived from N-phthaloylglycine as the common ABC-fragment. It was concluded that the correct structure of the 2(5H)-furanone D-ring is essential to retain full biological activity.

  DOI：

  10.1021/jf9604652
• 作为产物：
  描述：

  4-苯基四氢呋喃-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 生成 5-bromo-4-phenyl-2(5H)-furanone
  参考文献：
  名称：

  通过芳烃重氮盐与2,5-二氢呋喃的Heck反应快速合成4-芳基-γ-丁内酯，-呋喃-2（5H）-和-5-烷氧基呋喃-2（5H）-

  摘要：

  描述了涉及2,5-二氢呋喃的Heck反应和随后的迭代NBS氧化反应的4-取代呋喃-2（5H）-酮的异常简单而短的合成序列。

  DOI：

  10.1016/0040-4039(96)01994-6

文献信息

• <i>N</i>-Phthaloylglycine-Derived Strigol Analogues. Influence of the D-Ring on Seed Germination Activity of the Parasitic Weeds <i>Striga hermonthica</i> and <i>Orobanche crenata</i>
  作者：Jan Willem J. F. Thuring、Harry H. Bitter、Margreet M. de Kok、Gérard H. L. Nefkens、Annemiek M. D. A. van Riel、Binne Zwanenburg

  DOI：10.1021/jf9604652

  日期：1997.6.1

  Several strigol analogues with modifications in the D-ring were synthesized and assayed for germination stimulatory activity of seeds of Striga hermonthica and Orobanche crenata. All of these D-ring analogues are derived from N-phthaloylglycine as the common ABC-fragment. It was concluded that the correct structure of the 2(5H)-furanone D-ring is essential to retain full biological activity.
• An expeditious synthesis of 4-aryl-γ-butyrolactones, -furan-2(5H)-ones and -5-alkoxyfuran-2(5H)-ones via Heck-reaction of arenediazonium salts with 2,5-dihydrofuran
  作者：Goverdhan Mehia、Saunitra Sengupta

  DOI：10.1016/0040-4039(96)01994-6

  日期：1996.11

  An exceptionally simple and short synthetic sequence to 4-substituted furan-2(5H)-ones involving a Heck reaction on 2,5-dihydrofuran and subsequent iterative NBS oxidation is described.

  描述了涉及2,5-二氢呋喃的Heck反应和随后的迭代NBS氧化反应的4-取代呋喃-2（5H）-酮的异常简单而短的合成序列。