(Z)-5-benzylidene-3-bromo-2,5-dihydrofuran-2-one | 208194-66-5

• 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: (Z)-5-benzylidene-3-bromo-2,5-dihydrofuran-2-one
• 英文别名: (5Z)-5-benzylidene-3-bromofuran-2-one
• CAS: 208194-66-5
• 化学式: C₁₁H₇BrO₂
• 分子量: 251.079
• InChiKey: COUGDSLUYXXJAE-TWGQIWQCSA-N

物化性质

• 沸点：
  368.055±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.677±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-1-phenyl-(2-tributylstannyl)ethene 、 (Z)-5-benzylidene-3-bromo-2,5-dihydrofuran-2-one 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 三苯胂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以65%的产率得到(5Z)-5-benzylidene-3-[(E)-2-phenylethenyl]furan-2-one
  参考文献：
  名称：

  Stepwise Cross-Couplings of a Dibromo-γ-methylenebutenolide as an Access to Z-Configured α-Alkenyl-γ-alkylidenebutenolides. Straightforward ­Synthesis of the Antibiotic Lissoclinolide

  摘要：

  Z-异构体的α-溴-γ-(溴亚甲基)丁烯酮是分别从α-天使醇内酯或乙酰丙酸通过三步和四步合成的。通过与不饱和的锡烷进行连续的Stille偶联反应，首先引入γ取代基，然后引入α取代基，这允许使用不同的第二种不饱和锡烷。因此，获得了α-烯基-γ-烷基亚丁烯内酯及其芳烃类似物，具有Z选择性。

  DOI：

  10.1055/s-2005-868506
• 作为产物：
  描述：

  (苯乙炔基)氯化锌 在 四(三苯基膦)钯 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (Z)-5-benzylidene-3-bromo-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones

  摘要：

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00322-0

文献信息

• Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives
  作者：Petr Šenel、Lucie Tichotová、Ivan Votruba、Vladimír Buchta、Marcel Špulák、Jiří Kuneš、Milan Nobilis、Ondřej Krenk、Milan Pour

  DOI：10.1016/j.bmc.2010.01.030

  日期：2010.3

  parent furanone structure were therefore prepared and evaluated. In line with the ease of elimination of the substituent from C5, low activities of the 5-alkoxy compounds were observed. On the other hand, their 5-aryloxymethyl congeners were found to be capable of liberating the antifungally active 5-methylene furanone into the testing medium. The antifungal effect of the 5-alkylidene derivatives was

  发现先前描述为高度抗真菌活性的5-乙酰氧基甲基-3-（4-溴苯基）-2,5-二氢呋喃-2-酮可通过DMSO异常消除C5处的酯基来提供相应的5-亚甲基衍生物在抗真菌试验条件下。由于后者具有与最初报道的抗真菌作用几乎相同的抗真菌作用，因此5-乙酰氧基甲基呋喃酮仅用作实际的抗真菌活性物质的前体。因此，制备并评估了一系列在母体呋喃酮结构的C5处具有烷氧基，芳氧基和亚烷基取代基的化合物。与从C5中消除取代基的容易性相一致，观察到5-烷氧基化合物的活性低。另一方面，发现它们的5-芳氧基甲基同源物能够将抗真菌活性的5-亚甲基呋喃酮释放到测试介质中。5-亚烷基衍生物的抗真菌作用对亚烷基部分的取代高度敏感。为了保持化合物的高活性，在烯丙基位置的取代基是必需的。细胞抑制活性的并行评估显示抗真菌活性衍生物对HeLa S3和CCRF-CEM系的中等活性。用5-亚甲基-3-（4-溴苯基）-2,5-二氢呋喃-2-酮处
• Stepwise Cross-Couplings of a Dibromo-γ-methylenebutenolide as an Access to <i>Z</i>-Configured α-Alkenyl-γ-alkylidenebutenolides. Straightforward ­Synthesis of the Antibiotic Lissoclinolide
  作者：Reinhard Brückner、Achim Sorg、Frederik Blank

  DOI：10.1055/s-2005-868506

  日期：——

  The Z-isomer of α-bromo-γ-(bromomethylene)butenol­ide was prepared from α-angelica lactone or levulinic acid in three and four steps, respectively. Successive Stille-couplings with an ­unsaturated stannane, with the potential to use a different second unsaturated stannane, involved the γ-substituent first and the α-substituent thereafter. Thereby, α-alkenyl-γ-alkylidenebutenolides and their arene analogs were obtained Z-selectively.

  Z-异构体的α-溴-γ-(溴亚甲基)丁烯酮是分别从α-天使醇内酯或乙酰丙酸通过三步和四步合成的。通过与不饱和的锡烷进行连续的Stille偶联反应，首先引入γ取代基，然后引入α取代基，这允许使用不同的第二种不饱和锡烷。因此，获得了α-烯基-γ-烷基亚丁烯内酯及其芳烃类似物，具有Z选择性。
• A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones
  作者：Renzo Rossi、Fabio Bellina、Luisa Mannina

  DOI：10.1016/s0040-4039(98)00322-0

  日期：1998.5

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.