ethyl 2-phenyl-4-hydroxythiophene-3-carboxylate | 1022-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 2-phenyl-4-hydroxythiophene-3-carboxylate
• 英文别名: 4-hydroxy-2-phenyl-3-thiophenecarboxylic acid ethyl ester；4-Hydroxy-2-phenyl-thiophen-3-carbonsaeure-aethylester；3-Ethoxycarbonyl-4-hydroxy-2-phenyl-thiophen；4-Hydroxy-2-phenyl-thiophen-carbonsaeure-(3)-aethylester；4-hydroxy-2-phenyl-thiophene-3-carboxylic acid ethyl ester；4-Hydroxy-3-aethoxycarbonyl-2-phenyl-thiophen；3-Thiophenecarboxylic acid, 4-hydroxy-2-phenyl-, ethyl ester；ethyl 4-hydroxy-2-phenylthiophene-3-carboxylate
• CAS: 1022-06-6
• 化学式: C₁₃H₁₂O₃S
• 分子量: 248.302
• InChiKey: HHZBUAFTFOSISN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-phenyl-4-hydroxythiophene-3-carboxylate 在 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 以90%的产率得到5-[(E)-Hydroxyimino]-4-oxo-2-phenyl-4,5-dihydro-thiophene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  4-羟基-5-肟基-3-噻吩羧酸酯与肼的反应。吡唑基硫代异羟肟酸的形成

  摘要：

  已经研究了4-羟基-5-氧亚氨基-3-噻吩羧酸盐与肼和取代的肼的反应。已经显示反应的产物是吡唑-3-或5-硫代异羟肟酸，而不是贝纳利和席尔伯斯特伦先前描述的。提出了两种替代机制来解释区域化学结果。吡唑-3-和5-硫代异羟肟酸的结构以及相应的腈已通过独立合成，与已知化合物进行比较以及质子和碳磁共振以及远距离HETCOR实验得到了证明。

  DOI：

  10.1002/jhet.5570340210
• 作为产物：
  描述：

  2-巯基-S-硫代苯甲酰乙酸 在 rhodium(II) octanoate 、 三乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-羰基二咪唑 作用下， 以 苯 为溶剂， 反应 46.0h， 生成 ethyl 2-phenyl-4-hydroxythiophene-3-carboxylate
  参考文献：
  名称：

  Rhodium(II) Catalyzed Cyclization of Diazo Thiocarbonyl Compounds for Heterocycloic Synthesis

  摘要：

  The mesoionic thioisomunchnone system was prepared from the rhodium(II) acetate catalyzed cyclization of a diazothioamide and was found to undergo smooth 1,3-dipolar cycloaddition with N-phenylmaleimide. In contrast to this system, the rhodium(II) reaction of an alpha-diazo-beta-oxo ester containing a thiocarbonyl group produced a cyclic thiocarbonyl ylide which extruded sulfur from a transient episulfide intermediate.

  DOI：

  10.3987/com-92-s29

文献信息

• Rhodium(II) Catalyzed Cyclization of Diazo Thiocarbonyl Compounds for Heterocycloic Synthesis
  作者：Albert Padwa、Frederic R. Kinder、William R. Nadler、Lin Zhi

  DOI：10.3987/com-92-s29

  日期：——

  The mesoionic thioisomunchnone system was prepared from the rhodium(II) acetate catalyzed cyclization of a diazothioamide and was found to undergo smooth 1,3-dipolar cycloaddition with N-phenylmaleimide. In contrast to this system, the rhodium(II) reaction of an alpha-diazo-beta-oxo ester containing a thiocarbonyl group produced a cyclic thiocarbonyl ylide which extruded sulfur from a transient episulfide intermediate.
• Reaction of 4-hydroxy-5-oximino-3-thiophenecarboxylates with hydrazines. Formation of pyrazolylthiohydroxamic acids
  作者：R. L. Robey、C. A. Alt、E. E. Van Meter

  DOI：10.1002/jhet.5570340210

  日期：1997.3

  The reactions of 4-hydroxy-5-oximino-3-thiophenecarboxylates with hydrazine and substituted hydrazines have been investigated. The products of the reactions have been shown to be pyrazole-3- or 5-thiohydroxamic acids rather than the hydrazones previously described by Benary and Silberstrom. Two alternate mechanisms are proposed which account for the regiochemical outcome. The structures of the pyrazole-3-

  已经研究了4-羟基-5-氧亚氨基-3-噻吩羧酸盐与肼和取代的肼的反应。已经显示反应的产物是吡唑-3-或5-硫代异羟肟酸，而不是贝纳利和席尔伯斯特伦先前描述的。提出了两种替代机制来解释区域化学结果。吡唑-3-和5-硫代异羟肟酸的结构以及相应的腈已通过独立合成，与已知化合物进行比较以及质子和碳磁共振以及远距离HETCOR实验得到了证明。