3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one | 329328-49-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one
• 英文别名: 3-bromo-4-(4-methylthiophenyl)-2(5H)-furanone；2-bromo-3-(4-methylsulfanyl-phenyl)-2-buten-4-olide；2(5H)-Furanone, 3-bromo-4-[4-(methylthio)phenyl]-；4-bromo-3-(4-methylsulfanylphenyl)-2H-furan-5-one
• CAS: 329328-49-6
• 化学式: C₁₁H₉BrO₂S
• 分子量: 285.161
• InChiKey: WPNUSSNBVFFESQ-UHFFFAOYSA-N

物化性质

• 沸点：
  441.6±45.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one 在 bis-triphenylphosphine-palladium(II) chloride Oxone 、 苄基三乙基氯化铵 、 cesium fluoride 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 生成 罗非昔布
  参考文献：
  名称：

  Reinvestigation of Mucohalic Acids, Versatile and Useful Building Blocks for Highly Functionalized α,β-Unsaturated γ-Butyrolactones

  摘要：

  [GRAPHICS]Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.

  DOI：

  10.1021/ol027122b
• 作为产物：
  描述：

  3,4-二溴呋喃-2(5H)-酮 、 4-甲硫基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 苄基三乙基氯化铵 、 cesium fluoride 作用下， 反应 72.0h， 以74%的产率得到3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one
  参考文献：
  名称：

  合成芳基[11C]甲基砜的通用方法：成像环氧合酶2表达的潜在PET探针。

  摘要：

  已经开发了一种通用的一锅法，用于将被掩蔽为丁酸酯的芳基硫醇部分转化为相应的11C-标记的甲基砜基团。这种方法的潜力已通过成功放射性合成几种高选择性环氧合酶2（COX-2）抑制剂（如罗非考昔，依托昔布和3-（4-甲基磺酰基苯基）-4-苯基-5）的11碳类似物得到了证明。 -三氟甲基异恶唑，收率高。11C标记的COX-2抑制剂获得的化学和放射化学纯度> 99％，比活度> 1000 Ci / mmol。

  DOI：

  10.1016/j.bmcl.2005.06.080

文献信息

• Preparation of aryl-substituted butenolides using mucohalic acids
  申请人：Blazecka Garth Peter

  公开号：US20050131239A1

  公开（公告）日：2005-06-16

  Methods and materials for preparing 3-aryl-2-buten-4-olides and 2,3-bisaryl-2-buten-4-olides are disclosed. The methods include reacting a mucohalic acid with a reducing agent to give a 2,3-dihalo-2-buten-4-olide, which undergoes at least one Pd catalyzed cross-coupling reaction with an arylboronic acid.

  制备3-芳基-2-丁烯-4-内酯和2,3-双芳基-2-丁烯-4-内酯的方法和材料被公开。这些方法包括将粘酸与还原剂反应以得到2,3-二卤代-2-丁烯-4-内酯，该卤代物至少与一种芳基硼酸进行钯催化的交叉偶联反应。
• Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones
  作者：Fabio Bellina、Chiara Anselmi、Stéphane Viel、Luisa Mannina、Renzo Rossi

  DOI：10.1016/s0040-4020(01)01017-1

  日期：2001.12

  4-Aryl-3-bromo-2(5H)-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5H)-furanone either with arylboronic acids in the presence of Ag2O and a catalytic amount of PdCl2(MeCN)2 or with aryl(trialkyl)stannanes in the presence of a catalyst precursor consisting of AsPh3 and a Pd(II) or a Pd(0) compound. These monobromo derivatives have been

  通过在Ag 2的存在下用芳基硼酸处理易得的3,4-二溴-2（5 H）-呋喃酮，以令人满意的产率选择性合成了4-Aryl-3-bromo-2（5 H）-呋喃酮在由AsPh 3和Pd（II）或Pd（0）化合物组成的催化剂前体存在下，由O和催化量的PdCl 2（MeCN）2或与芳基（三烷基）锡烷一起催化。这些一溴衍生物已被用作各种（Z）-4-芳基-5- [1-（芳基）亚甲基] -3-溴-2（5 H-呋喃酮，包括具有与报道的天然存在的rubrolide N相对应的结构的化合物。这些合成化合物的结构和立体化学均已通过NMR技术明确确定。
• Rossi; Bellina; Raugei, Synlett, 2000, # 12, p. 1749 - 1752
  作者：Rossi、Bellina、Raugei

  DOI：——

  日期：——
• Reinvestigation of Mucohalic Acids, Versatile and Useful Building Blocks for Highly Functionalized α,β-Unsaturated γ-Butyrolactones
  作者：Ji Zhang、Peter G. Blazecka、Daniel Belmont、James G. Davidson

  DOI：10.1021/ol027122b

  日期：2002.12.1

  [GRAPHICS]Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.
• A general method for the synthesis of aryl [11C]methylsulfones: Potential PET probes for imaging cyclooxygenase-2 expression
  作者：Vattoly J. Majo、Jaya Prabhakaran、Norman R. Simpson、Ronald L. Van Heertum、J. John Mann、J.S. Dileep Kumar

  DOI：10.1016/j.bmcl.2005.06.080

  日期：2005.10

  methylsulfone group. The potential of this methodology has been demonstrated by the successful radiosynthesis of carbon-11 analogues of several highly selective cyclooxygenase-2 (COX-2) inhibitors such as Rofecoxib, Etoricoxib, and 3-(4-methylsulfonylphenyl)-4-phenyl-5-trifluoromethyl isoxazole in high yield. The chemical and radiochemical purities obtained for the 11C-labeled COX-2 inhibitors are >99%

  已经开发了一种通用的一锅法，用于将被掩蔽为丁酸酯的芳基硫醇部分转化为相应的11C-标记的甲基砜基团。这种方法的潜力已通过成功放射性合成几种高选择性环氧合酶2（COX-2）抑制剂（如罗非考昔，依托昔布和3-（4-甲基磺酰基苯基）-4-苯基-5）的11碳类似物得到了证明。 -三氟甲基异恶唑，收率高。11C标记的COX-2抑制剂获得的化学和放射化学纯度> 99％，比活度> 1000 Ci / mmol。