5-氟-3-甲基苯并呋喃 | 33118-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 5-氟-3-甲基苯并呋喃
• 英文名称: 5-fluoro-3-methylbenzofuran
• 英文别名: 5-fluoro-3-methyl-benzofuran；5-fluoro-3-methyl-1-benzofuran；5-fluoro-3-methyl benzofuran；3-Methyl-5-fluorbenzofuran
• CAS: 33118-83-1
• 化学式: C₉H₇FO
• mdl: MFCD13191783
• 分子量: 150.152
• InChiKey: LZVAHYZQDSUVNN-UHFFFAOYSA-N

物化性质

• 沸点：
  22-25 °C(Press: 0.15 Torr)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5-氟-3-甲基苯并呋喃 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以28%的产率得到5-氟苯并呋喃-3-甲醛
  参考文献：
  名称：

  Structure−Activity Relationships for a Novel Series of Dopamine D2-like Receptor Ligands Based on N-Substituted 3-Aryl-8-azabicyclo[3.2.1]octan-3-ol

  摘要：

  Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K-i(D2R/MR) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2(L)R- or hD3R-transfected HEK 293 cells (31, K-i(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, K-i(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.

  DOI：

  10.1021/jm800532x
• 作为产物：
  描述：

  2-(2-乙酰基-4-氟苯氧基)乙酸 在 sodium acetate 、 乙酸酐 作用下， 反应 5.0h， 以81%的产率得到5-氟-3-甲基苯并呋喃
  参考文献：
  名称：

  WO2006/107784

  摘要：

  公开号：
• 作为试剂：
  描述：

  sodium acetate 、 2-(2-乙酰基-4-氟苯氧基)乙酸 、 水 在 乙醚 、 氢氧化钾 、 水 、 silica gel 、 hexanes 、 5-氟-3-甲基苯并呋喃 作用下， 以 乙酸酐 为溶剂， 反应 4.0h， 以to obtain the desired product, 5-fluoro-3-methyl benzofuran (59%, 1.77 mg)的产率得到5-氟-3-甲基苯并呋喃
  参考文献：
  名称：

  Pyridazinone aldose reductase inhibitors

  摘要：

  本发明涉及新型吡啶并咪唑酮化合物、包含这些化合物的制药组合物以及使用这些化合物和组合物的方法，以抑制醛固酮还原酶，降低山梨醇水平，从而降低果糖水平，并/或治疗或预防哺乳动物的糖尿病并发症，如糖尿病神经病变、糖尿病视网膜病变、糖尿病肾病、糖尿病心肌病、糖尿病微血管病和糖尿病大血管病。本发明还涉及为非糖尿病患者提供心脏保护的方法。本发明还涉及包含本发明的醛固酮还原酶抑制剂（ARI）和山梨醇脱氢酶抑制剂的组合物和工具箱，以及使用这些组合物或工具箱治疗或预防哺乳动物的上述糖尿病并发症的方法。本发明还涉及与本发明的ARIs的其他组合物，包括与腺苷酸激动剂的组合；NHE-1抑制剂；糖原磷酸化酶抑制剂；选择性5-羟色胺再摄取抑制剂；GABA激动剂；降压剂；3-羟基-3-甲基谷氨酰辅酶A还原酶抑制剂；磷酸二酯酶-5抑制剂；以及降糖剂。

  公开号：

  US20020143017A1

文献信息

• [EN] 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE COMPOUNDS FOR THE TREATMENT OF TUBERCULOSIS<br/>[FR] COMPOSES 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE POUR LE TRAITEMENT DE LA TUBERCULOSE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2005042542A1

  公开（公告）日：2005-05-12

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: (1)in the above formula (1), R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R1 and -(CH2)nR2 may form a spiro ring represented by the formula (30) below, together with the adjacent carbon atom (in the formula below, RRR represents a piperidyl group which may have substituents on the piperidine ring), (30)and R2 represents a benzothiazolyloxy group, quinolyloxy group, pyridyloxy group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供了一种由以下一般式表示的2,3-二氢-6-硝基咪唑[2,1-b]噁唑化合物：(1)在上述式(1)中，R1代表氢原子或C1-C6烷基，n代表0至6的整数，R1和-(CH2)nR2可以与下面的式(30)一起形成一个螺环，与相邻的碳原子一起（在下面的式中，RRR代表可能在哌啶环上具有取代基的哌啶基），(30)和R2代表苯并噻唑氧基、喹啉氧基、吡啶氧基或类似物。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型耐酸细菌具有出色的杀菌作用。
• Palladium(II)-Catalyzed Transformation of 3-Alkylbenzofurans to [2,3′-Bibenzofuran]-2′(3′H)-ones: Oxidative Dimerization of 3-Alkylbenzofurans
  作者：Beom Shin Cho、Young Keun Chung

  DOI：10.1021/acs.joc.6b02864

  日期：2017.2.17

  An unprecedented oxidative dimerization by palladium catalysis has been developed using PhI(OPiv)2 as a by-standing oxidant. This provides a facile method for the synthesis of quaternary 2,3′-bibenzofuran-2′(3′)-ones from readily accessible substrates. A plausible mechanism involving a Pd(II)–Pd(IV) catalytic cycle is proposed; a trace amount of water is required for subsequent oxidation.

  使用PhI（OPiv）2作为辅助氧化剂，已经开发出前所未有的钯催化氧化二聚反应。这提供了从容易获得的底物合成季2,3'-联苯并呋喃-2'（3'）-的简便方法。提出了涉及Pd（II）–Pd（IV）催化循环的合理机制。后续的氧化需要痕量的水。
• [EN] PYRIDAZINONE ALDOSE REDUCTASE INHIBITORS<br/>[FR] INHIBITEURS PYRIDAZINONE D'ALDOSE RÉDUCTASE
  申请人：PFIZER PROD INC

  公开号：WO2002079198A1

  公开（公告）日：2002-10-10

  The present invention relates to novel pyridazinone compounds, pharmaceutical compositions comprising those compounds and to methods of using such compounds and compositions to inhibit aldose reductase, lower sorbitol levels and, thus, lower fructose levels, and/or treat or prevent diabetic complications such as diabetic neuropathy, diabetic retinopathy, diabetic nephropathy, diabetic cardiomyopathy, diabetic microangiopathy and diabetic macroangiopathy in mammals. This invention also relates to methods of affording cardioprotection to subjects not suffering from diabetes. This invention also relates to pharmaceutical compositions and kits comprising a combination of an aldose reductase inhibitor (ARI) of this invention and a sorbitol dehydrogenase inhibitor and to methods of using such compositions or kits to treat or prevent the above diabetic complications in mammals. This invention also relates to other combinations with the ARIs of this invention, including combinations with adenosine agonists; NHE-1 inhibitors; glycogen phosphorylase inhibitors; selective serotonin reuptake inhibitors; GABA agonists; antihypertensive agents; 3-hydroxy-3-methylglutaryl coenzyme A reductase-inhibitors; phosphodiesterase-5 inhibitors; and to glucose lowering agents.

  本发明涉及新型吡啶二酮化合物、包含这些化合物的制药组合物以及使用这些化合物和组合物的方法，以抑制醛糖还原酶、降低山梨醇水平，从而降低果糖水平，并/或治疗或预防哺乳动物的糖尿病并发症，如糖尿病神经病、糖尿病视网膜病、糖尿病肾病、糖尿病心肌病、糖尿病微血管病和糖尿病大血管病。本发明还涉及为非糖尿病患者提供心脏保护的方法。本发明还涉及包含本发明的醛糖还原酶抑制剂（ARI）和山梨醇脱氢酶抑制剂的组合物和工具箱，以及使用这些组合物或工具箱治疗或预防哺乳动物的上述糖尿病并发症的方法。本发明还涉及其他与本发明的ARI结合的组合物，包括与腺苷酸激动剂的组合物；NHE-1抑制剂；糖原磷酸化酶抑制剂；选择性5-羟色胺再摄取抑制剂；GABA激动剂；降压药物；3-羟基-3-甲基谷氨酰辅酶A还原酶抑制剂；磷酸二酯酶-5抑制剂；以及降血糖药物。
• [EN] COMBINATIONS OF ALDOSE REDUCTASE INHIBITORS AND CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] COMBINAISONS D'INHIBITEURS D'ALDOSE REDUCTASE ET INHIBITEURS DE CYCLO-OXYGENASE 2
  申请人：PFIZER PROD INC

  公开号：WO2002087584A1

  公开（公告）日：2002-11-07

  This invention relates to pharmaceutical compositions and kits comprising pyridazinone compounds and cyclooxygenase-2 inhibitors, therapeutic methods of treatment or prevention of certain complications arising from diabetes mellitus in mammals and therapeutic methods of treatment or prevention of cardiac tissue ischemia in mammals.

  本发明涉及含有吡啶并咪唑酮化合物和环氧合酶-2抑制剂的药物组合物和套装，以及治疗或预防哺乳动物糖尿病引起的某些并发症和心脏组织缺血的治疗方法。
• Therapies relating to combinations of aldose reductase inhibitors and cyclooxygenase-2
  申请人：Pfizer Inc

  公开号：US20040198740A1

  公开（公告）日：2004-10-07

  This invention relates to pharmaceutical compositions and kits comprising pyridazinone compounds and cyclooxygenase-2 inhibitors, therapeutic methods of treatment or prevention of certain complications arising from diabetes mellitus in mammals and therapeutic methods of treatment or prevention of cardiac tissue ischemia in mammals.

  本发明涉及药物组合物和工具包，包括吡啶并咪唑酮化合物和环氧合酶-2抑制剂，用于治疗或预防哺乳动物糖尿病引起的某些并发症的治疗方法和用于治疗或预防哺乳动物心脏组织缺血的治疗方法。