3-fluoro-N-hydroxy-4-methoxybenzimidoyl chloride | 677728-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-fluoro-N-hydroxy-4-methoxybenzimidoyl chloride
• 英文别名: 3-fluoro-N-hydroxy-4-methoxybenzenecarboximidoyl chloride
• CAS: 677728-80-2
• 化学式: C₈H₇ClFNO₂
• mdl: MFCD22419955
• 分子量: 203.6
• InChiKey: DTSYHJRTWLCQJV-UHFFFAOYSA-N

物化性质

• 沸点：
  327.1±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 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：
  41.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-fluoro-N-hydroxy-4-methoxybenzimidoyl chloride 、 烯丙基腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)acetonitrile
  参考文献：
  名称：

  Novel derivatives of ISO-1 as potent inhibitors of MIF biological function

  摘要：

  A series of novel 1,2,4-oxadiazole, phthalimide, amide and other derivatives of ISO-1 were synthesized and probed for inhibition of macrophage migration inhibitory factor (MIF) activity. Several compounds inhibited MIF enzymatic activity at levels better than ISO-1. Of note, compounds 7, 22, 23, 24, 25 and 27 inhibited the spontaneous secretion/release/recognition of MIF from freshly isolated human peripheral blood mononuclear cells and, more importantly, inhibited the MIF-induced production of interleukin-6 (IL-6) and/or interleukin-1b (IL-1b) significantly better than ISO-1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.052
• 作为产物：
  描述：

  3-氟-4-甲氧基苯甲醛 在 盐酸羟胺 作用下， 反应 3.0h， 生成 3-fluoro-N-hydroxy-4-methoxybenzimidoyl chloride
  参考文献：
  名称：

  蒙脱土Cu（II）催化多米诺骨牌一锅多组分合成3,5-二取代异恶唑

  摘要：

  已经开发了一种简单有效的单锅多组分方法，该方法使用可回收的蒙脱石粘土负载的Cu（II）/ NaN 3催化体系，在水性条件下直接从相应的醛和末端炔烃直接合成3,5-二取代的异恶唑。“多米诺”一锅式MCR方法涉及醛的羟基胺化，然后氯化，然后生成反应性“腈”，该炔与炔烃进行1,3-偶极环加成反应，生成3,5-二取代异恶唑。该方法操作简单，区域选择性，经济，并且具有出色的官能团相容性，可以高收率合成结构多样的异恶唑。

  DOI：

  10.1016/j.tetlet.2013.04.102

文献信息

• Stereospecific 1,4‐Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes
  作者：Kai Yang、Feng Zhang、Tongchang Fang、Guan Zhang、Qiuling Song

  DOI：10.1002/anie.201906057

  日期：2019.9.16

  Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer

  本文报道了用于由肟氯化物和芳基硼​​酸合成单几何型酮肟的立体有规的1,4-金属盐重排。该策略在温和的反应条件下具有宽泛的底物范围和出色的立体选择性。与常规方法相比，可以选择性地并且排他地获得不对称二芳基肟的每种构型以及芳基烷基酮肟的热力学上较不稳定的Z异构体。一类未开发的分子，不对称二芳基肟和芳基烷基肟的Z异构体的反应性使得能够有效地获得具有单一构型的相应异喹啉，异喹啉N-氧化物和酰胺。
• Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains
  作者：Hamish S. Sutherland、Adrian Blaser、Iveta Kmentova、Scott G. Franzblau、Baojie Wan、Yuehong Wang、Zhenkun Ma、Brian D. Palmer、William A. Denny、Andrew M. Thompson

  DOI：10.1021/jm901378u

  日期：2010.1.28

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.