2-(苄氧基)-5-氟苯甲醛 | 312314-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(苄氧基)-5-氟苯甲醛
• 英文名称: 2-(benzyloxy)-5-fluorobenzaldehyde
• 英文别名: 2-benzyloxy-5-fluoro-benzaldehyde；2-benzyloxy-5-fluorobenzaldehyde；5-fluoro-2-phenylmethoxybenzaldehyde
• CAS: 312314-37-7
• 化学式: C₁₄H₁₁FO₂
• 分子量: 230.239
• InChiKey: DGBMOFXIJPHQAW-UHFFFAOYSA-N

物化性质

• 熔点：
  46 °C
• 沸点：
  369.3±27.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(苄氧基)-5-氟苯甲醛 在 咪唑 、 盐酸 、 sodium tetrahydroborate 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 C₃₅H₃₀N₂O₂ 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 碘 、 sodium hydride 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 三乙胺 、 甲烷磺酰基叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 、 mineral oil 为溶剂， 25.0 ℃ 、405.33 kPa 条件下， 反应 0.08h， 生成 methyl (R)-6-fluorochroman-2-carboxylate
  参考文献：
  名称：

  对映选择性铜催化的分子内酚O ？H键插入：手性2-羧基二氢苯并呋喃，二氢苯并吡喃和四氢苯并氧杂环庚烷的合成

  摘要：

  有效：一个铜催化卡宾成酚类的O对映选择性分子内插入 H键已经研制成功。该方法可用于在温和和中性条件下以高收率和出色的对映选择性合成标题化合物（参见方案）。NaBAr F =四[3,5-双（三氟甲基）苯基]硼酸钠。

  DOI：

  10.1002/anie.201209455
• 作为产物：
  描述：

  4-氟苯酚 在 potassium carbonate 、 magnesium 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.5h， 生成 2-(苄氧基)-5-氟苯甲醛
  参考文献：
  名称：

  Effect of Ring Fluorination on the Pharmacology of Hallucinogenic Tryptamines

  摘要：

  A series of fluorinated analogues of the hallucinogenic tryptamines N,N-diethyltryptamine (DET), 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT, psilocin), and 5-methoxy-DMT was synthesized to investigate possible explanations for the inactivity of 6-fluoro-DET as a hallucinogen and to determine the effects of fluorination on the molecular recognition and activation of these compounds at serotonin receptor subtypes. The target compounds were evaluated using in vivo behavioral assays for hallucinogen-like and 6-HT1A agonist activity and in vitro radioligand competition assays for their affinity at 5-HT2A, 5-HT2C, and 5-HT1A receptor sites. Functional activity at the 5-HT2A receptor was determined for all compounds. In addition, for some compounds functional activity was determined at the 5-HT1A receptor. Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues. One of the tryptamines, 4-fluoro-5-methoxy-DMT (6), displayed high 5-HT1A agonist activity, with potency greater than that of the 5-HT1A agonist 8-OH-DPAT. The ED50 Of 6 in the two-lever drug discrimination paradigm using rats trained to discriminate the 5-HT1A agonist LY293284 was 0.17 mu mol/kg, and the K-i at [H-3] 8-OH-DPAT-labeled 5-HT1A receptors was 0.23 nM. The results indicate that fluorination of hallucinogenic tryptamines generally has little effect on 5-HT2A/2C receptor affinity or intrinsic activity. Affinity at the 5-HT1A receptor was reduced, however, in all but one example, and all of the compounds tested were full agonists but with reduced functional potency at this serotonin receptor subtype. The one notable exception was 4-fluoro-5-methoxy-DMT (6), which had markedly enhanced 5-HT1A receptor affinity and functional potency. Although it is generally considered that hallucinogenic activity results from 5-HT2A receptor activation, the present results suggest a possible role for involvement of the 5-HT1A receptor with tryptamines.

  DOI：

  10.1021/jm000339w

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• TRIAZOLE ACC INHIBITORS AND USES THEREOF
  申请人：Gilead Apollo, LLC

  公开号：US20170166584A1

  公开（公告）日：2017-06-15

  The present invention provides triazole compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了三唑化合物，可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及其组合物和使用方法。
• [EN] HEXAHYDROPYRAZINOBENZ- OR -PYRIDO-OXAZEPINES CARRYING AN OXYGEN-CONTAINING SUBSTITUENT AND USE THEREOF IN THE TREATMENT OF 5-HT2C-DEPENDENT DISORDERS<br/>[FR] HEXAHYDROPYRAZINOBENZ- OU -PYRIDO-OXAZÉPINES TRANSPORTANT UN SUBSTITUANT CONTENANT DE L'OXYGÈNE ET SON UTILISATION POUR LE TRAITEMENT D'AFFECTIONS CONDITIONNÉES PAR 5-HT2C
  申请人：ABBVIE DEUTSCHLAND

  公开号：WO2017089458A1

  公开（公告）日：2017-06-01

  The present invention relates to compound of formula (I) (I) wherein the variables are as defined in the claims and the description. The invention further relates to a pharmaceutical composition containing such compounds, to their use as modulators, especially agonists or partial agonists, of the 5-HT2C receptor, to their use for preparing a medicament for the prevention or treatment of conditions and disorders which respond to the modulation of 5-HT2C receptor, and to methods for preventing or treating conditions and disorders which respond to the modulation of 5-HT2C receptor.

  本发明涉及通式(I)的化合物，其中变量如权利要求和说明书中所定义。本发明还涉及含有此类化合物的药物组合物，涉及它们作为调节剂，特别是5-HT2C受体的激动剂或部分激动剂的使用，涉及它们用于制备预防或治疗对5-HT2C受体调节有反应的病症和疾病的药物，以及涉及预防或治疗对5-HT2C受体调节有反应的病症和疾病的方法。
• [EN] 1-PHENYL-SUBSTITUTED HETEROCYCLYL DERIVATIVES AND THEIR USE AS PROSTAGLANDIN D2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'HÉTÉROCYCLYLE SUBSTITUÉS PAR UN 1-PHÉNYLE ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RÉCEPTEURS DE LA PROSTAGLANDINE D2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2012004722A1

  公开（公告）日：2012-01-12

  302 Abstract The present invention relates to 1-phenyl-substituted heterocyclyl derivatives of the formula (I), O Y R 5 R 6 N R 2 R 3 R 4 X Z R 1 R 7 R 7 R 10 n (I) 5 wherein X, Y, Z, n, R 1, R 2, R 3, R 4, R 5, R 6, R 7 and R 10 are as described in the description and their use as prostaglandin receptor modulators, most particularly as prostaglandin D 2 receptor modulators, in the treatment of various prostaglandin-mediated diseases and disorders, to pharmaceutical compositions containing these compounds and to processes for their preparation. 10

  本发明涉及公式(I)的1-苯基取代的杂环基衍生物，其中X、Y、Z、n、R1、R2、R3、R4、R5、R6、R7和R10如描述中所述，并且它们作为前列腺素受体调节剂的用途，特别是作为前列腺素D2受体调节剂，在治疗各种前列腺素介导的疾病和紊乱中的用途，以及含有这些化合物的制药组合物和其制备方法。
• BENZENE DERIVATIVE
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US20210332009A1

  公开（公告）日：2021-10-28

  A compound represented by general formula (I) (in the formula, all symbols are as described in the description) or a salt thereof has a potent nerve-protecting and/or -repairing activity, and therefore can be used as a therapeutic agent for neuropathy (e.g., chronic inflammatory demyelinating polyneuropathy, Guillain-Barre syndrome, periarteritis nodosa, allergic vasculitis, diabetic peripheral neuropathy, entrapment neuropathy, peripheral neuropathy associated with the administration of a chemotherapeutic drug, or peripheral neuropathy associated with Charcot-Marie-Tooth disease).

  通式（I）表示的化合物（在公式中，所有符号如描述中所述）或其盐具有强大的神经保护和/或修复活性，因此可用作神经病变的治疗剂（例如，慢性炎症性脱髓鞘性多发性神经病、吉兰-巴雷综合征、周围动脉炎、过敏性血管炎、糖尿病周围神经病变、神经卡压病变、与化疗药物治疗相关的周围神经病变，或与沙科-玛丽-图斯病相关的周围神经病变）。