4-oxo-4-(1-tosyl-1H-pyrrol-3-yl)butanoic acid | 194352-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-oxo-4-(1-tosyl-1H-pyrrol-3-yl)butanoic acid
• 英文别名: 4-[1-(tosyl)-3-pyrrolyl]-4-oxobutyric acid；4-[1-(4-Methylphenyl)sulfonylpyrrol-3-yl]-4-oxobutanoic acid
• CAS: 194352-59-5
• 化学式: C₁₅H₁₅NO₅S
• 分子量: 321.354
• InChiKey: QTYOYOHMZRCZHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-oxo-4-(1-tosyl-1H-pyrrol-3-yl)butanoic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 1-(1,3-Benzodioxol-5-yl)-4-[1-(4-methylphenyl)sulfonylpyrrol-3-yl]butan-1-ol
  参考文献：
  名称：

  分子内Friedel-Crafts反应合成（±）-γ-瓜环烷

  摘要：

  摘要 通过使用N-甲苯磺酰基吡咯作为主要的结构单元，可以实现γ-二十烷的全合成。合成过程同时使用分子间和分子内Friedel-Crafts反应，以及后期吡咯中间体的完全非对映选择性氢化。 通过使用N-甲苯磺酰基吡咯作为主要的结构单元，可以实现γ-二十烷的全合成。合成过程同时使用分子间和分子内Friedel-Crafts反应，以及后期吡咯中间体的完全非对映选择性氢化。

  DOI：

  10.1055/s-0036-1589067
• 作为产物：
  描述：

  对甲苯磺酰氯 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.75h， 生成 4-oxo-4-(1-tosyl-1H-pyrrol-3-yl)butanoic acid
  参考文献：
  名称：

  A novel necroptosis inhibitor—necrostatin-21 and its SAR study

  摘要：

  An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.073

文献信息

• Derivatives of 4-hydroxybutanoic acid and of its higher homologue as ligands of $g(g)-hydroxybutyrate (ghb) receptors, pharmaceutical compositions containing same and pharmaceutical uses
  申请人：Bourguignon Jean-Jacques

  公开号：US20050113366A1

  公开（公告）日：2005-05-26

  The invention concerns the field of synthesis organic chemistry applied to the pharmaceutical field and concerns novel derivatives of 4-hydroxybutanoic acid and its higher homologue, 5-hydroxypentanoic acid, their crotonic homologues, pharmaceutical compositions containing them and their pharmaceutical uses. Said novel derivatives are capable of binding with γ-hydroxybutyrate (GHB)-specific receptors and hence capable of exhibiting agonist or antagonist properties, in particular for treating sleep disorders, anxiety and general diseases of the central nervous system. The invention also concerns compounds of general formula (I) wherein the substituents are as defined in the description.

  该发明涉及合成有机化学领域应用于制药领域，涉及4-羟基丁酸及其较高同系物5-羟基戊酸的新颖衍生物，它们的丁烯酸同系物，含有它们的药物组合物以及它们的药用。所述新颖衍生物能够与γ-羟基丁酸盐（GHB）特异性受体结合，因此能够表现出激动剂或拮抗剂特性，特别用于治疗睡眠障碍、焦虑和中枢神经系统的一般疾病。该发明还涉及一般式（I）的化合物，其中取代基如描述中所定义。
• Design of Chiral Poly(Pyrroles)
  作者：Susanne Pleus、Marion Schwientek

  DOI：10.1080/00397919708004998

  日期：1997.9

  The synthesis of three 3-substituted and one N-substituted chiral pyrrole derivatives as well as their electropolymerization conditions are described. The new materials thus obtained possess recognition properties as enantioselective electrodes.
• Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel–Crafts Reaction
  作者：Bao Doan、Xin Tan、Chin Ang、Roderick Bates

  DOI：10.1055/s-0036-1589067

  日期：2017.10

  Abstract A total synthesis of γ-lycorane has been achieved by employing N-tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel–Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate. A total synthesis of γ-lycorane has been achieved by employing N-tosylpyrrole as a key building block

  摘要 通过使用N-甲苯磺酰基吡咯作为主要的结构单元，可以实现γ-二十烷的全合成。合成过程同时使用分子间和分子内Friedel-Crafts反应，以及后期吡咯中间体的完全非对映选择性氢化。 通过使用N-甲苯磺酰基吡咯作为主要的结构单元，可以实现γ-二十烷的全合成。合成过程同时使用分子间和分子内Friedel-Crafts反应，以及后期吡咯中间体的完全非对映选择性氢化。
• A novel necroptosis inhibitor—necrostatin-21 and its SAR study
  作者：Zhijie Wu、Ying Li、Yu Cai、Junying Yuan、Chengye Yuan

  DOI：10.1016/j.bmcl.2013.06.073

  日期：2013.9

  An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM. (C) 2013 Elsevier Ltd. All rights reserved.