(2S)-2-(1H-pyrrol-1-yl)glutaric acid | 46293-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-(1H-pyrrol-1-yl)glutaric acid
• 英文别名: (2S)-2-pyrrol-1-ylpentanedioic acid
• CAS: 46293-28-1
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: KMDQALUEPILHTH-ZETCQYMHSA-N

物化性质

• 沸点：
  391.5±32.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-(1H-pyrrol-1-yl)glutaric acid 在 Rh/Al₂O₃ 盐酸 、 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 3.0h， 生成 methyl 8-hydroxyoctahydroindolizine-5-carboxylate
  参考文献：
  名称：

  Bond, Timothy J.; Jenkins, Robert; Ridley, Andrew C., Journal of the Chemical Society. Perkin transactions I, 1993, # 19, p. 2241 - 2242

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 L-谷氨酸 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.75h， 以59%的产率得到(2S)-2-(1H-pyrrol-1-yl)glutaric acid
  参考文献：
  名称：

  The synthesis of chiral 1-(1H-pyrrole) derivatives

  摘要：

  Enantiomerically pure primary amines possessing an epimerizable center, such as alpha-amino acids and their ester hydrochlorides, undergo condensation with tetrahydro-2,5-dimethoxyfuran 2 in acetic acid or acetic acid containing sodium acetate at 80 degrees C for 30 min. to give the corresponding 1-(1H-pyrrolyl) derivatives with partial racemization (9-18%). By replacing the solvent with a stirred mixture of aqueous acetic acid and 1,2-dichloroethane in the case of the acids and with water-1,2-dichloroethane for the ester hydrochlorides, repetition of the previous experiment gives the corresponding pyrroles in high yield and with complete retention of configuration, beta-Aminoalcohols are also efficiently converted to their 1-(1H-pyrrolyl) derivatives in a stirred, warm mixture of aqueous acetic acid and 1,2-dichloroethane. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00111-5

文献信息

• [EN] 4-ALKYL SUBSTITUTED 3,4-DIHYDROPYRROLO[1,2-a]PYRAZIN-1(2H)-ONE DERIVATIVES AS KINASES INHIBITORS<br/>[FR] DÉRIVÉS 3,4-DIHYDROPYRROLO[1,2-A]PYRAZIN-1(2H)-ONE SUBSTITUÉ PAR 4-ALKYLE EN TANT QU'INHIBITEURS DE KINASES
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2013050448A1

  公开（公告）日：2013-04-11

  The present invention relates to 4-alkyl substituted 3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing such these compounds or the pharmaceutical compositions containing them.

  本发明涉及4-烷基取代的3,4-二氢吡咯并[1,2-a]吡嗪-1(2H)-酮衍生物，其调节蛋白激酶的活性，因此在治疗由失调的蛋白激酶活性引起的疾病方面具有用途。本发明还提供了制备这些化合物的方法，包括这些化合物的药物组合物，以及利用这些化合物或含有它们的药物组合物治疗疾病的方法。
• 4-ALKYL SUBSTITUTED 3,4-DIHYDROPYRROLO[1,2-a]PYRAZIN-1(2H)-ONE DERIVATIVES AS KINASES INHIBITORS
  申请人：NERVIANO MEDICAL SCIENCES S.R.L.

  公开号：US20140249146A1

  公开（公告）日：2014-09-04

  The present invention relates to 4-alkyl substituted 3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing such these compounds or the pharmaceutical compositions containing them.

  本发明涉及调节蛋白激酶活性的4-烷基取代的3,4-二氢吡咯并[1,2-a]吡嗪-1(2H)-酮衍生物，因此在治疗由蛋白激酶活性失调引起的疾病方面具有用途。本发明还提供了制备这些化合物的方法，包括这些化合物的药物组合物，以及利用这些化合物或含有它们的药物组合物治疗疾病的方法。
• Bond, Timothy J.; Jenkins, Robert; Ridley, Andrew C., Journal of the Chemical Society. Perkin transactions I, 1993, # 19, p. 2241 - 2242
  作者：Bond, Timothy J.、Jenkins, Robert、Ridley, Andrew C.、Taylor, Paul C.

  DOI：——

  日期：——
• The synthesis of chiral 1-(1H-pyrrole) derivatives
  作者：Charles W. Jefford、Fabienne de Villedon de Naide、Krzysztof Sienkiewicz

  DOI：10.1016/0957-4166(96)00111-5

  日期：1996.4

  Enantiomerically pure primary amines possessing an epimerizable center, such as alpha-amino acids and their ester hydrochlorides, undergo condensation with tetrahydro-2,5-dimethoxyfuran 2 in acetic acid or acetic acid containing sodium acetate at 80 degrees C for 30 min. to give the corresponding 1-(1H-pyrrolyl) derivatives with partial racemization (9-18%). By replacing the solvent with a stirred mixture of aqueous acetic acid and 1,2-dichloroethane in the case of the acids and with water-1,2-dichloroethane for the ester hydrochlorides, repetition of the previous experiment gives the corresponding pyrroles in high yield and with complete retention of configuration, beta-Aminoalcohols are also efficiently converted to their 1-(1H-pyrrolyl) derivatives in a stirred, warm mixture of aqueous acetic acid and 1,2-dichloroethane. Copyright (C) 1996 Elsevier Science Ltd