4,5-二氯-1H-吡咯-2-羧酸 | 39209-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4,5-二氯-1H-吡咯-2-羧酸
• 中文别名: 4,5-二氯-2-吡咯甲酸
• 英文名称: 4,5-dichloro-1H-pyrrole-2-carboxylic acid
• CAS: 39209-94-4
• 化学式: C₅H₃Cl₂NO₂
• mdl: MFCD08691218
• 分子量: 179.99
• InChiKey: MNMMKOBJLQMWLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 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：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  4,5-二氯-1H-吡咯-2-羧酸 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4,5-dichloro-1H-pyrrole-2-carboxylic acid (3-methoxy-4-prop-2-ynyloxybenzyloxy)amide
  参考文献：
  名称：

  Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs

  摘要：

  A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by H-1 NMR, C-13 NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 mu g mL(-1). Compound 2a and 3a exhibited good activities against P. piricola at low dosage. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.031
• 作为产物：
  描述：

  2,2,2-三氯-1-(4,5-二氯-1H-吡咯-2-基)乙酮 在 sodium hydroxide 作用下， 以 正己烷 、 水 为溶剂， 生成 4,5-二氯-1H-吡咯-2-羧酸
  参考文献：
  名称：

  4,5-Dihalopyrrole-2-carboxamides

  摘要：

  4,5-二卤吡咯-2-羧酰胺衍生物，通过相应的4,5-二卤吡咯-2-羧酸酰氯或相应的4,5-二卤吡咯-2-基三卤甲基酮与适当胺反应制备，可用作抗菌和除草剂。

  公开号：

  US04046775A1

文献信息

• Pyrrolyl oxyphenyl ketones
  申请人：Sterling Drug Inc.

  公开号：US04000160A1

  公开（公告）日：1976-12-28

  4,5-Dihalopyrrol-2-yl oxyphenyl ketones, prepared either by Friedel-Crafts condensation of a 4,5-dihalopyrrole-2-carboxylic acid halide with an appropriate hydroxy or lower-alkoxy-substituted benzene or by condensation of a hydroxy or lower-alkoxy-substituted benzaldehyde with pyrrole in the presence of sodium hydride followed by halogenation, with elemental chlorine or bromine, of the resulting pyrrol-2-yl oxyphenyl ketone, useful as antibacterial and antifungal agents.

  4,5-二卤吡咯-2-基氧基苯酮，通过将4,5-二卤吡咯-2-羧酸卤化物与适当的羟基或较低烷氧基取代的苯反应，或者通过在氢化钠存在下将羟基或较低烷氧基取代的苯甲醛与吡咯缩合后进行卤代反应（使用氯或溴元素），制备而成，可用作抗菌和抗真菌剂。
• INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20080181923A1

  公开（公告）日：2008-07-31

  Disclosure is provided for imidazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  提供了关于咪唑衍生物化合物的披露，这些化合物可以预防、去除和/或抑制生物膜的形成，包括这些化合物的组合物、包含这些化合物的设备，以及使用它们的方法。
• INHIBITION OF BIOFILMS IN PLANTS WITH IMIDAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20090143230A1

  公开（公告）日：2009-06-04

  Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an active compound as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an active compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or plant defense activator.

  本公开提供了一种防止、去除或抑制植物或其部分中微生物生物膜形成或微生物感染的方法，包括向其施加本文所述的活性化合物的有效量或其农业可接受的盐。还提供了增强微生物杀灭剂（例如，包括铜、抗生素、噬菌体等）和/或植物防御激活剂的方法，包括施加本文所述的活性化合物。还提供了包含本文所述的活性化合物在农业可接受载体中的组合物，并在某些实施例中，这些组合物进一步包括微生物杀灭剂（例如，包括铜、抗生素、噬菌体等）和/或植物防御激活剂。
• Herbicidal pyrrole-2-carboxamides
  申请人：Sterling Drug Inc.

  公开号：US03963480A1

  公开（公告）日：1976-06-15

  4,5-Dihalopyrrole-2-carboxamide derivatives, prepared by reaction of a corresponding 4,5-dihalopyrrole-2-carboxylic acid halide or a corresponding 4,5-dihalopyrrol-2-yl trihalomethyl ketone with an appropriate amine, have antibacterial and herbicidal activities.

  4,5-二卤吡咯-2-羧酰胺衍生物，通过相应的4,5-二卤吡咯-2-羧酸酰氯或相应的4,5-二卤吡咯-2-基三卤甲基酮与适当的胺反应制备，具有抗菌和除草活性。
• Gatekeeping Ketosynthases Dictate Initiation of Assembly Line Biosynthesis of Pyrrolic Polyketides
  作者：Dongqi Yi、Atanu Acharya、James C. Gumbart、Will R. Gutekunst、Vinayak Agarwal

  DOI：10.1021/jacs.1c02371

  日期：2021.5.26

  Assembly line biosynthesis of polyketide natural products involves checkpoints where identities of thiotemplated intermediates are verified before polyketide extension reactions are allowed to proceed. Determining what these checkpoints are and how they operate is critical for reprogramming polyketide assembly lines. Here we demonstrate that ketosynthase (KS) domains can perform this gatekeeping role

  聚酮化合物天然产物的流水线生物合成涉及检查点，在允许进行聚酮化合物延伸反应之前验证硫模板化中间体的身份。确定这些检查点是什么以及它们如何运行对于重新编程聚酮化合物装配线至关重要。在这里，我们证明了酮合酶 (KS) 域可以执行此守门角色。通过比较扩展吡咯基和卤化吡咯基底物的聚酮合酶的底物特异性，我们发现需要区分这两种底物的 KS 域具有高选择性。我们还发现 KS 活性位点中的氨基酸残基促进了这种选择性，并且这些残基适合进行合理的工程改造。另一方面，不需要在其天然生理环境中做出选择性决定的 KS 域是底物混杂的。我们还提供证据表明，通过非天然载体蛋白将底物输送到聚酮合酶会伴随着生物合成效率的降低。