methyl (Z)-(4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate | 1451878-34-4

• 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: methyl (Z)-(4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate
• 英文别名: methyl (4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate；methyl (2Z)-2-(4-bromo-3-methyl-5-oxofuran-2-ylidene)acetate
• CAS: 1451878-34-4
• 化学式: C₈H₇BrO₄
• 分子量: 247.045
• InChiKey: QIHJMDZZCCYNJC-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-(4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate 在 bis-triphenylphosphine-palladium(II) chloride 、 溶剂黄146 、 cesium fluoride 、 <15N>ammonium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 methyl (4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-[¹⁵N]pyrrol-2-ylidene)ethanoate
  参考文献：
  名称：

  Total synthesis and characterization of the bilirubin oxidation product (Z)-2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX B)

  摘要：

  Bilirubin oxidation end products (BOXes) show significant physiological effects and are connected to severe diseases such as subarachnoid hemorrhage induced cerebral vasospasm. BOX B (2-(4-ethenyl-3methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide) was prepared via a five-step synthesis starting from methyl (4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate that was vinylated and then reacted with NH4OAc, LiOH, (COCl)(2), and finally with ammonia yielding Z-BOX B. Derivatives of Z-BOX A and Z-BOX B with [N-15]labeled lactam rings were synthesized accordingly. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.108
• 作为产物：
  描述：

  3-溴-4-甲基呋喃-2,5-二酮 、 甲氧羰基亚甲基三苯基正膦 以 甲苯 为溶剂， 反应 6.0h， 以64%的产率得到methyl (Z)-(3-bromo-4-methyl-5-oxofuran-2(5H)-ylidene)ethanoate
  参考文献：
  名称：

  Total Synthesis and Detection of the Bilirubin Oxidation Product (Z)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX A)

  摘要：

  The selective total synthesis of the pure Z-isomer of BOX A (8a), a product of oxidative heme degradation with significant physiological impact, was achieved in four to six steps starting from 3-bromo-4-methylfuran-2,5-dione (1). Z-BOX A forms a strong hydrogen bridge framework in the crystalline state. LC-MS techniques allow identification and characterization of isomeric forms of BOX A.

  DOI：

  10.1021/ol402221b

文献信息

• Total Synthesis and Detection of the Bilirubin Oxidation Product (<i>Z</i>)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2<i>H</i>-pyrrol-2-ylidene)ethanamide (<i>Z</i>-BOX A)
  作者：Maurice Klopfleisch、Raphael A. Seidel、Helmar Görls、Hannes Richter、Rainer Beckert、Wolfgang Imhof、Markus Reiher、Georg Pohnert、Matthias Westerhausen

  DOI：10.1021/ol402221b

  日期：2013.9.6

  The selective total synthesis of the pure Z-isomer of BOX A (8a), a product of oxidative heme degradation with significant physiological impact, was achieved in four to six steps starting from 3-bromo-4-methylfuran-2,5-dione (1). Z-BOX A forms a strong hydrogen bridge framework in the crystalline state. LC-MS techniques allow identification and characterization of isomeric forms of BOX A.
• Total synthesis and characterization of the bilirubin oxidation product (Z)-2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX B)
  作者：Raphael A. Seidel、Björn Schowtka、Maurice Klopfleisch、Toni Kühl、Andreas Weiland、Alexander Koch、Helmar Görls、Diana Imhof、Georg Pohnert、Matthias Westerhausen

  DOI：10.1016/j.tetlet.2014.09.108

  日期：2014.11

  Bilirubin oxidation end products (BOXes) show significant physiological effects and are connected to severe diseases such as subarachnoid hemorrhage induced cerebral vasospasm. BOX B (2-(4-ethenyl-3methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide) was prepared via a five-step synthesis starting from methyl (4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate that was vinylated and then reacted with NH4OAc, LiOH, (COCl)(2), and finally with ammonia yielding Z-BOX B. Derivatives of Z-BOX A and Z-BOX B with [N-15]labeled lactam rings were synthesized accordingly. (C) 2014 Elsevier Ltd. All rights reserved.