5-(4-formylphenyl)thiophene-2-carboxylic acid methyl ester

• 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: 5-(4-formylphenyl)thiophene-2-carboxylic acid methyl ester
• 英文别名: 5-(4-Formyl-phenyl)-thiophene-2-carboxylic acid methyl ester；methyl 5-(4-formylphenyl)thiophene-2-carboxylate
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: OLTMJKPSUFCFMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苯乙胺 、 5-(4-formylphenyl)thiophene-2-carboxylic acid methyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 5-[4-(phenethylamino-methyl)-phenyl]-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  [EN] BIARYL LINKED HYDROXAMATES: PREPARATION AND PHARMACEUTICAL APPLICATIONS
  [FR] HYDROXAMATES LIES AU BIARYLE: PREPARATION ET APPLICATIONS PHARMACEUTIQUES

  摘要：

  本发明涉及羟肟酸酯化合物，这些化合物是组蛋白去乙酰化酶的抑制剂。更具体地，本发明涉及含有联苯基的化合物及其制备方法。这些化合物可能作为治疗增殖性疾病以及与组蛋白去乙酰化酶活性有关的其他疾病的药物而有用。公式（I），其中Z是单键或C1-C4烃基，A是芳香环，B是芳香环。

  公开号：

  WO2005040161A1
• 作为产物：
  描述：

  甲醇 、 4-甲酰基苯硼酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium diacetate 、 potassium carbonate 、 三氟乙酸 作用下， 生成 5-(4-formylphenyl)thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Microwave-Assisted Aqueous Suzuki Cross-Coupling Reactions

  摘要：

  The poly(ethylene glycol) ester of bromo-, iodo-, and triflate-para-substituted benzoates are smoothly cross-coupled with aryl boronic acids (Suzuki reaction) under "ligandless" palladium acetate catalysis in water. The reaction proceeds without organic cosolvent under conventional thermal conditions (70 degrees C, 2 h) and under microwave irradiation (75 W, 2-4 min). The polymeric support remains stable under both reaction conditions. Whereas conventional thermal conditions induced ester cleavage (up to 45%), this side reaction is suppressed when microwave conditions are employed. Aryl nonaflates give fair yields under these conditions. Non-polymer-bound aryl halides form biaryls in good to excellent yields in water/poly(ethylene glycol) mixtures under microwave irradiation (4 min, 75 W).

  DOI：

  10.1021/jo982135h

文献信息

• Biaryl linked hydroxamates: preparation and pharmaceutical applications
  申请人：Stunkel Walter

  公开号：US20070167499A1

  公开（公告）日：2007-07-19

  The present invention relates to hydroxamate compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to biaryl containing compounds and methods for their preparation. These compounds may be useful as medicaments for the treatment of proliferative disorders as well as other diseases involving, relating to or associated with enzymes having histone deacetylase activities. Formula (I), where Z is a single bond or C 1 -C 4 hydrocarbon, A is an aromatic ring, B is an aromatic ring.

  本发明涉及一种羟酸酰胺化合物，其是组蛋白去乙酰化酶的抑制剂。更具体地说，本发明涉及含有双芳基的化合物及其制备方法。这些化合物可以作为药物用于治疗增生性疾病以及涉及、与组蛋白去乙酰化酶活性有关的其他疾病。其中，公式（I）中，Z为单键或C1-C4烃基，A为芳香环，B为芳香环。
• BIARYL LINKED HYDROXAMATES: PREPARATION AND PHARMACEUTICAL APPLICATIONS
  申请人：S*Bio Pte Ltd

  公开号：EP1682538A1

  公开（公告）日：2006-07-26
• EP1682538A4
  申请人：——

  公开号：EP1682538A4

  公开（公告）日：2009-05-27
• Microwave-Assisted Aqueous Suzuki Cross-Coupling Reactions
  作者：Carsten G. Blettner、Wilfried A. König、Wolfgang Stenzel、Theo Schotten

  DOI：10.1021/jo982135h

  日期：1999.5.1

  The poly(ethylene glycol) ester of bromo-, iodo-, and triflate-para-substituted benzoates are smoothly cross-coupled with aryl boronic acids (Suzuki reaction) under "ligandless" palladium acetate catalysis in water. The reaction proceeds without organic cosolvent under conventional thermal conditions (70 degrees C, 2 h) and under microwave irradiation (75 W, 2-4 min). The polymeric support remains stable under both reaction conditions. Whereas conventional thermal conditions induced ester cleavage (up to 45%), this side reaction is suppressed when microwave conditions are employed. Aryl nonaflates give fair yields under these conditions. Non-polymer-bound aryl halides form biaryls in good to excellent yields in water/poly(ethylene glycol) mixtures under microwave irradiation (4 min, 75 W).
• [EN] BIARYL LINKED HYDROXAMATES: PREPARATION AND PHARMACEUTICAL APPLICATIONS<br/>[FR] HYDROXAMATES LIES AU BIARYLE: PREPARATION ET APPLICATIONS PHARMACEUTIQUES
  申请人：S BIO PTE LTD

  公开号：WO2005040161A1

  公开（公告）日：2005-05-06

  The present invention relates to hydroxamate compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to biaryl containing compounds and methods for their preparation. These compounds may be useful as medicaments for the treatment of proliferative disorders as well as other diseases involving, relating to or associated with enzymes having histone deacetylase activities. Formula (I), where Z is a single bond or C1-C4 hydrocarbon, A is an aromatic ring, B is an aromatic ring.

  本发明涉及羟肟酸酯化合物，这些化合物是组蛋白去乙酰化酶的抑制剂。更具体地，本发明涉及含有联苯基的化合物及其制备方法。这些化合物可能作为治疗增殖性疾病以及与组蛋白去乙酰化酶活性有关的其他疾病的药物而有用。公式（I），其中Z是单键或C1-C4烃基，A是芳香环，B是芳香环。