methyl 2-acetyl-4-(3-fluorophenyl)-4-oxobutanoate | 947400-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetyl-4-(3-fluorophenyl)-4-oxobutanoate
• CAS: 947400-59-1
• 化学式: C₁₃H₁₃FO₄
• 分子量: 252.242
• InChiKey: VFXUHEBLLGCLTL-UHFFFAOYSA-N

物化性质

• 沸点：
  383.0±37.0 °C(predicted)
• 密度：
  1.208±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-acetyl-4-(3-fluorophenyl)-4-oxobutanoate 在 甲醇 、 sodium hydroxide 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 5-(3-fluorophenyl)-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  PYRROLE DERIVATIVE OR SALT THEREOF

  摘要：

  公开号：

  EP1988075B1
• 作为产物：
  描述：

  3-氟溴代苯乙酮 、 乙酰乙酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以65%的产率得到methyl 2-acetyl-4-(3-fluorophenyl)-4-oxobutanoate
  参考文献：
  名称：

  催化不对称Paal-Knorr反应高阻转选择性合成芳基吡咯

  摘要：

  首次开发了一种利用催化不对称 Paal-Knorr 反应获得对映体纯芳基吡咯的通用且有效的方法。以高产率获得了范围广泛的轴向手性芳基吡咯，具有良好到出色的对映选择性。成功的关键是使用包含路易斯酸和手性磷酸的联合酸催化系统来实现有效的对映控制。值得注意的是，在上述不对称反应中观察到了意想不到的对映选择性的溶剂依赖性反转。

  DOI：

  10.1021/jacs.6b09634

文献信息

• Organocatalytic Atroposelective Synthesis of N−N Axially Chiral Indoles and Pyrroles by De Novo Ring Formation
  作者：Ke‐Wei Chen、Zhi‐Han Chen、Shuang Yang、Shu‐Fang Wu、Yu‐Chen Zhang、Feng Shi

  DOI：10.1002/anie.202116829

  日期：2022.4.19

  The first highly atroposelective construction of N−N axially chiral indole scaffolds was established via a new strategy of de novo ring formation, which is also applicable for the synthesis of N−N axially chiral bispyrroles. Such N−N axially chiral heterocycles can be converted into chiral organocatalysts. They may also display potent anticancer activity, thus offering new members of the N−N atropisomer

  通过从头形成环的新策略建立了第一个高度选择性的 N-N 轴向手性吲哚支架构建，该策略也适用于 N-N 轴向手性双吡咯的合成。这种NN轴向手性杂环可以转化为手性有机催化剂。它们还可能显示出有效的抗癌活性，从而为 N-N 阻转异构体家族的新成员提供了在合成和药物化学中具有前景的应用。
• Pyrrole Derivative or Salt Thereof
  申请人：Seo Ryushi

  公开号：US20090036421A1

  公开（公告）日：2009-02-05

  [Problem] To provide a compound which may be used for the prevention and/or treatment of diseases in which 5-HT 2B receptor and 5-HT 7 receptor are concerned, particularly for the treatment of irritable bowel syndrome (IBS). [Means for Resolution] It was found that a pyrrole derivative characterized by the possession of a guanidinocarbonyl group or amido group as a substituent group at the 3-position, or a pharmaceutically acceptable salt thereof, has a strong antagonism for both of the 5-HT 2B receptor and 5-HT 7 receptor. In addition, the compound of the present invention having the antagonistic activity for both of the receptors showed a good pharmacological action in comparison with the case in which an antagonist selective for either one of the receptors was used alone. Based on the above, the compound of the present invention is useful for the prevention and/or treatment of diseases in which 5-HT 2B receptor and 5-HT 7 receptor are concerned, particularly for the treatment of irritable bowel syndrome (IBS).

  [问题] 提供一种可用于预防和/或治疗与5-HT2B受体和5-HT7受体有关的疾病，特别是治疗肠易激综合征（IBS）的化合物。 [解决方案] 发现一种吡咯衍生物，在其3位具有胍基甲酰基基团或酰胺基团作为取代基团，或其药学上可接受的盐，具有对5-HT2B受体和5-HT7受体的强拮抗作用。此外，与仅使用对其中一种受体选择性拮抗剂相比，具有对两种受体拮抗活性的本发明化合物显示出良好的药理作用。基于上述，本发明化合物对于预防和/或治疗与5-HT2B受体和5-HT7受体有关的疾病，特别是治疗肠易激综合征（IBS）是有用的。
• Pyrrole derivative or salt thereof
  申请人：Astellas Pharma Inc.

  公开号：US08222274B2

  公开（公告）日：2012-07-17

  [Problem] To provide a compound which may be used for the prevention and/or treatment of diseases in which 5-HT2B receptor and 5-HT7 receptor are concerned, particularly for the treatment of irritable bowel syndrome (IBS). [Means for Resolution] It was found that a pyrrole derivative characterized by the possession of a guanidinocarbonyl group or amido group as a substituent group at the 3-position, or a pharmaceutically acceptable salt thereof, has a strong antagonism for both of the 5-HT2B receptor and 5-HT7 receptor. In addition, the compound of the present invention having the antagonistic activity for both of the receptors showed a good pharmacological action in comparison with the case in which an antagonist selective for either one of the receptors was used alone. Based on the above, the compound of the present invention is useful for the prevention and/or treatment of diseases in which 5-HT2B receptor and 5-HT7 receptor are concerned, particularly for the treatment of irritable bowel syndrome (IBS).

  [问题] 提供一种化合物，可用于预防和/或治疗与5-HT2B受体和5-HT7受体有关的疾病，特别是治疗肠易激综合征（IBS）。 [解决方法] 发现一种吡咯衍生物，其在3位具有胍基羰基基团或酰胺基团作为取代基团，或其药学上可接受的盐，具有对5-HT2B受体和5-HT7受体的强烈拮抗作用。此外，本发明的化合物具有对两种受体的拮抗活性，与仅使用选择性拮抗剂的情况相比，表现出良好的药理作用。基于以上，本发明的化合物对于预防和/或治疗与5-HT2B受体和5-HT7受体有关的疾病，特别是治疗肠易激综合征（IBS）非常有用。
• US8222274B2
  申请人：——

  公开号：US8222274B2

  公开（公告）日：2012-07-17
• Highly Atroposelective Synthesis of Arylpyrroles by Catalytic Asymmetric Paal–Knorr Reaction
  作者：Lei Zhang、Jian Zhang、Ji Ma、Dao-Juan Cheng、Bin Tan

  DOI：10.1021/jacs.6b09634

  日期：2017.2.8

  efficient method for accessing enantiomerically pure arylpyrroles by utilizing the catalytic asymmetric Paal-Knorr reaction has been developed for the first time. A wide range of axially chiral arylpyrroles were obtained in high yields with good to excellent enantioselectivities. The key to success is the use of the combined-acid catalytic system involving a Lewis acid and a chiral phosphoric acid for

  首次开发了一种利用催化不对称 Paal-Knorr 反应获得对映体纯芳基吡咯的通用且有效的方法。以高产率获得了范围广泛的轴向手性芳基吡咯，具有良好到出色的对映选择性。成功的关键是使用包含路易斯酸和手性磷酸的联合酸催化系统来实现有效的对映控制。值得注意的是，在上述不对称反应中观察到了意想不到的对映选择性的溶剂依赖性反转。