2-acetyl-5-fluoro-benzonitrile | 1363508-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-5-fluoro-benzonitrile
• 英文别名: 2-Acetyl-5-fluorobenzonitrile
• CAS: 1363508-10-4
• 化学式: C₉H₆FNO
• 分子量: 163.151
• InChiKey: QPYDBZLGNHINTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-5-fluoro-benzonitrile 在 sodium tetrahydroborate 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 48.5h， 以80%的产率得到6-fluoro-3-methylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s
• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 盐酸 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 乙二醇二乙醚 、 水 为溶剂， 反应 4.08h， 生成 2-acetyl-5-fluoro-benzonitrile
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s

文献信息

• [EN] NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2014202458A1

  公开（公告）日：2014-12-24

  The present invention discloses compounds according to Formula I: Wherein R 1a, R 1b, R 2, R 4, R5, R 6, R 7, R 8, W, X, Y, Z, Cy, and the subscript a are as defined herein. The present invention relates to compounds inhibiting autotaxin (NPP2 or ENPP2), methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving fibrotic diseases,proliferative diseases, inflammatory diseases, autoimmune diseases, respiratory diseases, cardiovascular diseases, neurodegenerative diseases, dermatological disorders, and/or abnormal angiogenesis associated diseases by administering the compound of the invention.

  本发明公开了根据式I的化合物：其中R 1a、R 1b、R 2、R 4、R5、R 6、R 7、R 8、W、X、Y、Z、Cy和下标a如本文所定义。本发明涉及抑制自体脂肪酶（NPP2或ENPP2）的化合物，其制备方法，包含其的药物组合物，以及使用该化合物进行预防和/或治疗涉及纤维化疾病、增殖性疾病、炎症性疾病、自身免疫疾病、呼吸系统疾病、心血管疾病、神经退行性疾病、皮肤病和/或与异常血管生成相关疾病的方法。
• [EN] COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT DESTINÉS À TRAITER LES TROUBLES INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2014139882A1

  公开（公告）日：2014-09-18

  The present invention discloses compounds according to Formula I: Wherein R1a, R1b, R2, R4, R5, R6a, R6b, R7, R8, W, X, Cy, and the subscript a are as defined herein. The present invention relates to compounds inhibiting autotaxin (NPP2 or ENPP2), methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving fibrotic diseases, proliferative diseases, inflammatory diseases, autoimmune diseases, respiratory diseases, cardiovascular diseases, neurodegenerative diseases, dermatological disorders, and/or abnormal angiogenesis associated diseasesby administering the compound of the invention.

  本发明公开了根据式I的化合物：其中R1a、R1b、R2、R4、R5、R6a、R6b、R7、R8、W、X、Cy和下标a如本文所定义。本发明涉及抑制自体脂肪酶（NPP2或ENPP2）的化合物，其制备方法，包含其的药物组合物，以及使用该化合物进行预防和/或治疗涉及纤维化疾病、增生性疾病、炎症性疾病、自身免疫疾病、呼吸系统疾病、心血管疾病、神经退行性疾病、皮肤病和/或与异常血管生成相关疾病的方法。
• NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS
  申请人：Galapagos NV

  公开号：US20170362227A1

  公开（公告）日：2017-12-21

  The present invention discloses compounds according to Formula I: Wherein R 1a , R 1b , R 2 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8 , W, X, Cy, and the subscript a are as defined herein. The present invention relates to compounds inhibiting autotaxin (NPP2 or ENPP2), methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving fibrotic diseases, proliferative diseases, inflammatory diseases, autoimmune diseases, respiratory diseases, cardiovascular diseases, neurodegenerative diseases, dermatological disorders, and/or abnormal angiogenesis associated diseases by administering the compound of the invention.

  本发明揭示了符合公式I的化合物：其中，R1a，R1b，R2，R4，R5，R6a，R6b，R7，R8，W，X，Cy和下标a如本文所定义。本发明涉及抑制自体脂肪酸酰肌醇磷酸酯酶（NPP2或ENPP2）的化合物，其制备方法，包含它们的制药组合物和使用它们的治疗方法，用于预防和/或治疗涉及纤维化疾病，增生性疾病，炎症性疾病，自身免疫性疾病，呼吸系统疾病，心血管疾病，神经退行性疾病，皮肤疾病和/或异常血管生成相关疾病，通过给予本发明的化合物。
• 一种含三氮唑结构的二苯醚类化合物的防治或控制植物病害的用途、方法及其组合物
  申请人：海利尔药业集团股份有限公司

  公开号：CN115088722A

  公开（公告）日：2022-09-23

  本发明属于农药领域，具体涉及一种含三氮唑结构的二苯醚类化合物的用途、使用方法及其组合物，所述化合物具有式(I)结构：式中各基团定义如说明书中所示；本发明还公开了如上所述的化合物的使用方法。本发明的含三氮唑结构的二苯醚类化合物具有比已知化合物更佳的杀菌活性以及更优秀的作物安全性，尤其对植物锈病、褐腐病及轮纹病等具有极佳的生物活性。
• Compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders
  申请人：Galapagos NV

  公开号：US10125132B2

  公开（公告）日：2018-11-13

  The present invention discloses compounds according to Formula I: Wherein R1a, R1b, R2, R4, R5, R6a, R6b, R7, R8, W, X, Cy, and the subscript a are as defined herein. The present invention relates to compounds inhibiting autotaxin (NPP2 or ENPP2), methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving fibrotic diseases, proliferative diseases, inflammatory diseases, autoimmune diseases, respiratory diseases, cardiovascular diseases, neurodegenerative diseases, dermatological disorders, and/or abnormal angiogenesis associated diseases by administering the compound of the invention.

  本发明公开了符合式 I 的化合物： 其中 R1a、R1b、R2、R4、R5、R6a、R6b、R7、R8、W、X、Cy 和下标 a 如本文所定义。 本发明涉及抑制自体表皮生长因子（NPP2 或 ENPP2）的化合物、其生产方法、包含其的药物组合物和使用其的治疗方法，用于通过施用本发明化合物预防和/或治疗涉及纤维化疾病、增殖性疾病、炎症性疾病、自身免疫性疾病、呼吸系统疾病、心血管疾病、神经退行性疾病、皮肤病和/或异常血管生成相关疾病。