2-fluoro-3,4-dihydroxybenzaldehyde | 61338-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-fluoro-3,4-dihydroxybenzaldehyde
• 英文别名: 2-fluoroprotocatechualdehyde
• CAS: 61338-95-2
• 化学式: C₇H₅FO₃
• 分子量: 156.113
• InChiKey: OPJXZKBYNBTYPN-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  280.4±35.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-fluoro-3,4-dihydroxybenzaldehyde 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4-Chloro-phenyl)-(3-cyclopentyloxy-2-fluoro-4-methoxy-phenyl)-methanol
  参考文献：
  名称：

  Discovery of L-791,943: A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor

  摘要：

  Structure-activity relationship studies directed toward improving the potency and metabolic stability of CDP-840 (3) resulted in the discovery of L-791,943 (1 In) as a potent (HWB TNF-alpha = 0.67 muM) and orally active phosphodiesterase type 4 (PDE4) inhibitor. This compound, which bears a stable bis-difluoromethoxy catechol and a pendant hexafluorocarbinol, exhibited a long half-life in rat and in squirrel monkey. It is well tolerated in ferret with an emetic threshold greater than 30 mg/kg (po) and was found to be active in the ovalbumin-induced bronchoconstriction model in guinea pig and in the ascaris-induced bronchoconstriction models in sheep and squirrel monkey. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00190-7
• 作为产物：
  描述：

  2-氟-3,4-二甲氧基苯甲醛 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到2-fluoro-3,4-dihydroxybenzaldehyde
  参考文献：
  名称：

  环氟化异丙肾上腺素的合成和肾上腺素能激动剂特性。

  摘要：

  通过还原相应的环氟化3,4-双（苄氧基）苯乙醇胺和丙酮之间形成的席夫碱，然后在草酸存在下进行还原性脱苄基反应，合成2-氟-，5-氟-和6-氟异丙基肾上腺素。酸产生结晶的中性草酸酯。在分离的豚鼠心房中确定了明显的β-肾上腺素能。2-氟和5-氟异丙肾上腺素与（+/-）-异丙肾上腺素等效，而6-氟异丙肾上腺素实际上是无活性的。任何氟代异丙肾上腺素均未显示出α-肾上腺素能激动剂活性（豚鼠主动脉）。氟异丙肾上腺素从大鼠脑分离的膜制剂中置换出α-和β-特异性放射性配体与器官制剂的反应一致。从而，明显的氟诱导的特异性是由于受体结合位点的特异性。讨论了氟取代的影响，涉及6-氟取代基对异丙肾上腺素β-激动剂性能的明显负面影响，由于2-氟取代基引起的效力缺乏任何增加以及氟-取代的可能性诱导芳环电子密度的变化，这可能是氟代异丙肾上腺素和氟去甲肾上腺素的氟诱导的特异性的合理原因。

  DOI：

  10.1021/jm00348a014

文献信息

• PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
  申请人：Philippe Michel

  公开号：US20100028280A1

  公开（公告）日：2010-02-04

  The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

  该发明涉及一种直发角蛋白纤维的拉直过程，包括：(i)将至少两种变性剂含有的拉直组合物涂抹到角蛋白纤维上的步骤，(ii)使用加热装置将角蛋白纤维的温度升高至110至250°C的步骤。
• Halogen substituted .alpha.-(aminoalkyl)-3,4-dihydroxybenzyl alcohols
  申请人：SmithKline Corporation

  公开号：US03976695A1

  公开（公告）日：1976-08-24

  Halogen substituted .alpha.-(aminoalkyl)-3,4-dihydroxybenzyl alcohols having .beta.-adrenergic stimulant activity, particularly as selective bronchodilators. The .alpha.-aminomethyl derivatives are prepared by the condensation of an appropriately substituted styrene oxide with a primary amine followed by removal of the ether protective group(s). The .alpha.-aminoethyl or .alpha.-aminopropyl derivatives are prepared by the condensation of an appropriately substituted .alpha.-bromoalkyl phenyl ketone with an N-benzyl secondary amine followed by reduction of the ketone moiety and removal of the ether protective group(s).

  具有β-肾上腺素激动剂活性的卤代α-(氨基烷基)-3,4-二羟基苯甲醇，特别是作为选择性支气管扩张剂。α-氨甲基衍生物通过适当取代的苯乙烯环氧化物与一级胺缩合制备，随后去除醚保护基。α-氨乙基或α-氨丙基衍生物通过适当取代的α-溴烷基苯酮与N-苄基二级胺缩合制备，随后还原酮基团并去除醚保护基。
• Method for straightening keratinous fibers using heating means and an aromatic compound
  申请人：L'Oreal

  公开号：US11044978B2

  公开（公告）日：2021-06-29

  The invention concerns a method for straightening keratinous fibers including: (i) a step of applying on the keratinous fibers a hair straightening composition containing at least one polyhydroxylated aromatic compound, (ii) a step of increasing the temperature of the keratinous fibers, using heating means, to a temperature ranging between 110 and 250° C.

  本发明涉及一种拉直角质纤维的方法，包括：(i) 在角质纤维上涂抹含有至少一种多羟基芳香族化合物的拉直头发组合物，(ii) 使用加热装置将角质纤维的温度提高到 110 至 250 摄氏度之间。
• Synthesis and biological activities of fluorinated chalcone derivatives
  作者：Chika Nakamura、Nobuhide Kawasaki、Hideki Miyataka、Ezhuthachan Jayachandran、In Ho Kim、Kenneth L Kirk、Takeo Taguchi、Yoshio Takeuchi、Hitoshi Hori、Toshio Satoh

  DOI：10.1016/s0968-0896(01)00319-4

  日期：2002.3

  We have designed and synthesized new 5-lipoxygenase inhibitors, fluorinated 3,4-dihydroxychalcones, and evaluated their biological activities with respect to antiperoxidation activity and in vitro antitumor activities. All fluorinated chalcones tested showed 5-lipoxygenase inhibition on rat basophilic leukemia-1 (RBL-1) cells and inhibitory action on Fe3+ -ADP induced NADPH-dependent lipid peroxidation in rat liver microsomes. The potencies were comparable or better to that of the lead 3,4-dihydroxychalcone. 6-Fluoro-3,4-dihydroxy-2',4'-dimethoxy chalcone (7) was the most effective compound in the in vitro assay using a human cancer cell line panel (HCC panel) consisting of 39 systems. (C) 2002 Elsevier Science Ltd. All rights reserved.
• KIRK, K. L.;CANTACUZENE, D.;COLLINS, B.;CHEN, G. T.;NIMIT, Y.;CREVELING, +, J. MED. CHEM., 1982, 25, N 6, 680-684
  作者：KIRK, K. L.、CANTACUZENE, D.、COLLINS, B.、CHEN, G. T.、NIMIT, Y.、CREVELING, +

  DOI：——

  日期：——