3,5-二氟-2-甲氧基苯甲醛 | 131782-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二氟-2-甲氧基苯甲醛
• 中文别名: 2-甲氧基-3,5-二氟苯甲醛
• 英文名称: 3,5-difluoro-2-methoxybenzaldehyde
• CAS: 131782-50-8
• 化学式: C₈H₆F₂O₂
• mdl: MFCD06246883
• 分子量: 172.131
• InChiKey: OHIQTYCWUIZOBK-UHFFFAOYSA-N

物化性质

• 沸点：
  243.9±35.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3,5-二氟-2-甲氧基苯甲醛 在 咪唑 、 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-<(tert-butyldimethylsilyl)oxy>-3,5-difluoro-2-methoxybenzene
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024
• 作为产物：
  描述：

  3,5-difluoro-2-methoxy-4-(trimethylsilyl)benzaldehyde 在 2,2,2-三氟乙醇 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3,5-二氟-2-甲氧基苯甲醛
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024

文献信息

• Naphthalenylmethoxypiperidines as renin inhibitors
  申请人：Hoffmann-La Roche Inc.

  公开号：US06376672B1

  公开（公告）日：2002-04-23

  The present invention relates to compound of formula (I) wherein R1, R2 and R3 are as defined in the description and claims and pharmaceutically acceptable salts thereof. The compounds are useful for treating diseases associated with restenosis, glaucoma, cardiac infarct, high blood pressure and end organ damage, e.g. cardiac insufficiency and kidney insufficiency.

  本发明涉及式(I)的化合物 式中R1、R2和R3定义如描述和权利要求所述，以及药用可接受的盐。这些化合物用于治疗与再狭窄、青光眼、心肌梗死、高血压和终末器官损伤有关的疾病，例如心功能不全和肾功能不全。
• Silver(I)-Catalyzed Route to Pyrroles: Synthesis of Halogenated Pseudilins as Allosteric Inhibitors for Myosin ATPase and X-ray Crystal Structures of the Protein-Inhibitor Complexes
  作者：René Martin、Célia Risacher、André Barthel、Anne Jäger、Arndt W. Schmidt、Sabine Richter、Markus Böhl、Matthias Preller、Krishna Chinthalapudi、Dietmar J. Manstein、Herwig O. Gutzeit、Hans-Joachim Knölker

  DOI：10.1002/ejoc.201402177

  日期：2014.7

  and pentachloropseudilin represent a new class of isoform-specific allosteric inhibitors of myosin ATPase. Herein, we describe an application of the silver(I)-catalyzed cycloisomerization of N-(homopropargyl)toluenesulfonamides to the total syntheses of these natural products and several non-natural analogues. Moreover, we examine the inhibitiory effect of pentahalogenated pseudilins on myosin ATPase

  五卤化 2-芳基吡咯型生物碱 pentabrompseudilin 和 pentachloropseudin 代表了一类新的肌球蛋白 ATP 酶的异构体特异性变构抑制剂。在此，我们描述了银 (I) 催化的 N-（高炔丙基）甲苯磺酰胺环异构化在这些天然产物和几种非天然类似物的全合成中的应用。此外，我们检查了五卤化假素对肌球蛋白 ATP 酶活性的抑制作用。
• 一种二芳基喹啉化合物的制备方法
  申请人：湖南华腾制药有限公司

  公开号：CN108689990A

  公开（公告）日：2018-10-23

  本发明提供了一种二芳基喹啉衍生物的制备方法，以6‑溴‑2‑甲氧基喹啉和三取代苯甲醛为起始原料，经锂化加成得到仲醇，再经羟基还原，卤原子取代，再锂化加成的方法得到目标产物，该化合物在药物化学领域具有广泛的应用前景。
• Benzyl amines, a process for their production and their use as anti-inflammatory agents
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1878717A1

  公开（公告）日：2008-01-16

  The present invention relates to the compounds of formula I, processes for their production and their use as anti-inflammatory agents.

  本发明涉及式I化合物，其生产工艺以及作为抗炎药物的用途。
• Total Synthesis of Pentabromo- and Pentachloropseudilin, and Synthetic Analogues-Allosteric Inhibitors of Myosin ATPase
  作者：René Martin、Anne Jäger、Markus Böhl、Sabine Richter、Roman Fedorov、Dietmar J. Manstein、Herwig O. Gutzeit、Hans-Joachim Knölker

  DOI：10.1002/anie.200903743

  日期：2009.10.12

  Stopping myo: The total syntheses of the title compounds have been achieved using a highly efficient silver(I)‐catalyzed cyclization of N‐tosyl‐homopropargylamines. The pseudilin derivatives represent a novel class of myosin inhibitors. A new allosteric binding pocket of the Dictyostelium myosin‐2 motor domain has been identified for pentabromopseudilin (1) by using an X‐ray crystal structure determination

  终止肌细胞：使用高效的银（I）催化的N-甲苯磺酰基-高炔丙基胺的环化反应，可以实现标题化合物的总合成。假单胞菌素衍生物代表一类新型的肌球蛋白抑制剂。通过抑制物-蛋白质复合物的X射线晶体结构测定，已经确定了五溴单丝菌素（Ditabyoopseselin）（1）已确定了一个新的变种，即网柄菌肌球蛋白2运动域的变构结合口袋。