3-chloro-2,5-dihydroxybenzoic acid | 89692-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-2,5-dihydroxybenzoic acid
• CAS: 89692-72-8
• 化学式: C₇H₅ClO₄
• 分子量: 188.567
• InChiKey: MVFJOJHYMGUADK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-2,5-dihydroxybenzoic acid 在 titanium(IV) isopropylate 、 硫酸 、 四氯化钛 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 methyl 6-chloro-2-(3,4-dimethoxyphenyl)-5-hydroxy-3-methyl-2,3-dihydro-1-benzofuran-4-carboxylate
  参考文献：
  名称：

  Synthesis and SAR of 2,3‐Dihydro‐1‐benzofuran‐4‐carboxylates: Potent Salicylic Acid‐Based Lead Structures against Plant Stress

  摘要：

  AbstractNew 2,3‐dihydro‐1‐benzofuran‐4‐carboxylic acid derivatives have been identified as potent lead structures against drought and cold stress in crops starting from the synthetic exploration of stabilized analogs of the natural product lunularic acid. An optimized Lewis‐acid mediated cyclization gave a short and efficient access to the envisaged 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates. Enantioselective approaches were investigated to assess the potential impact of the chiral center on in vivo activity. Whilst 2,3‐dihydro‐1‐benzofuran‐4‐carboxamides and 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying phenyl substituents with electron‐withdrawing groups exhibited only low to moderate in vivo activity, the corresponding 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying optimized electron‐donating substituents in the phenyl moiety revealed strong in vivo activity, both against drought stress in several broad‐acre crops, as well as against cold stress in corn. Remarkably, several 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates showed stronger efficacy than the internal standards used in our in vivo SAR study.

  DOI：

  10.1002/ejoc.202200087
• 作为产物：
  描述：

  3-Chlor-2,5-dimethoxy-benzoesaeure 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-chloro-2,5-dihydroxybenzoic acid
  参考文献：
  名称：

  Synthesis and SAR of 2,3‐Dihydro‐1‐benzofuran‐4‐carboxylates: Potent Salicylic Acid‐Based Lead Structures against Plant Stress

  摘要：

  AbstractNew 2,3‐dihydro‐1‐benzofuran‐4‐carboxylic acid derivatives have been identified as potent lead structures against drought and cold stress in crops starting from the synthetic exploration of stabilized analogs of the natural product lunularic acid. An optimized Lewis‐acid mediated cyclization gave a short and efficient access to the envisaged 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates. Enantioselective approaches were investigated to assess the potential impact of the chiral center on in vivo activity. Whilst 2,3‐dihydro‐1‐benzofuran‐4‐carboxamides and 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying phenyl substituents with electron‐withdrawing groups exhibited only low to moderate in vivo activity, the corresponding 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying optimized electron‐donating substituents in the phenyl moiety revealed strong in vivo activity, both against drought stress in several broad‐acre crops, as well as against cold stress in corn. Remarkably, several 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates showed stronger efficacy than the internal standards used in our in vivo SAR study.

  DOI：

  10.1002/ejoc.202200087

文献信息

• USE OF SUBSTITUTED 2,3-DIHYDRO-1-BENZOFURAN-4-CARBOXYLIC ACIDS OR SALTS THEREOF AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS
  申请人：Bayer CropScience AG

  公开号：US20150322094A1

  公开（公告）日：2015-11-12

  Use of substituted 2,3-dihydro-1-benzofuran-4-carboxylic acids of the general formula (I) or salts thereof where the radicals in the general formula (I) are as defined in the description, for increasing stress tolerance in plants with respect to abiotic stress, for enhancing plant growth and/or for increasing plant yield, and specific processes for preparing the aforementioned compounds.

  使用通式（I）或其盐代替2,3-二氢-1-苯并呋喃-4-羧酸，其中通式（I）中的基团如描述中定义的，用于增加植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量，并用于制备上述化合物的特定过程。
• Dihalopropene compounds, processes for their preparation, compositions comprising them and their use as pesticides
  申请人：——

  公开号：US20040029886A1

  公开（公告）日：2004-02-12

  Dihalopropene compounds, process for their preparation, compositions comprising them and their use as pesticides What is described are dihalopropene compounds of the formula (I) 1 in which R 1 and R 2 are halogen, Y is —O—, —S— or —NH—, X is —O—, —S(O) r — or —NR 5 — (where r=0, 1, 2 and R 5 is hydrogen or C 1 -C 8 -alkyl), X′ is a direct C—C bond, —O—, —S(O) r — or —NR 5 — (where R 5 is as defined above), R 3 is hydrogen, halogen, nitro, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 3 -C 10 -cycloalkyl or has one of the meanings defined for A, A has the meaning given in the description (inter alia aryl, heterocyclyl), B is a divalent bridge having the meanings given in the description (inter alia alkylene) and R 4 is a monovalent C 6 -C 14 -aryl radical or nitrogen-containing heteroaryl radical having at least one ring heteroatom which has the meanings given in the description. These compounds can be used for preparing pesticides.

  本文描述的是一种公式（I）的二卤代丙烯化合物，其中R1和R2是卤素，Y为—O—，—S—或—NH—，X为—O—，—S（O）r—或—NR5—（其中r=0、1、2，R5为氢或C1-C8烷基），X'为直接的C—C键，—O—，—S（O）r—或—NR5—（其中R5如上所定义），R3为氢、卤素、硝基、氰基、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C3-C10环烷基或具有A所定义的含义（包括芳基、杂环烷基），A具有描述中给出的含义（包括芳基、杂环烷基），B为具有描述中给出的含义（包括烷基）的二价桥，R4为具有描述中给出的含义的单价C6-C14芳基基团或含氮杂环芳基基团，其中至少有一个环杂原子具有描述中给出的含义。这些化合物可用于制备杀虫剂。
• CHARGE CONTROL RESIN AND MANUFACTURING METHOD OF THE SAME
  申请人：YASUMATSU Masashi

  公开号：US20150025213A1

  公开（公告）日：2015-01-22

  Here is provided a charge control resin which is prompt in charge rising up, excellent in electrostatic charging propensity and easy in manufacturing. This charge control resin contains a polymer as an active ingredient having a constituent unit represented by following Formula (1) in the Formula (1), R 1 is independent of one another, and is a hydrogen atom, a hydroxyl group, a halogen atom, a carboxy-containing group, a straight-chained or branched alkyl group having 1-18 carbon atoms, or a straight-chained or branched alkoxy group having 1-18 carbon atoms; R 2 is a hydrogen atom, a hydroxyl group, a halogen atom, a carboxy-containing group, a straight-chained or branched alkyl group having 1-18 carbon atoms, or a straight-chained or branched alkoxy group having 1-18 carbon atoms; g is a number of 1-3; h is a number of 1-3; and M is a hydrogen atom, an alkali metal, a straight-chained or branched alkyl group having 1-18 carbon atoms, an ammonium radical or a mixture of any of these.

  这里提供了一种电荷控制树脂，它在电荷上升方面快速，具有优异的静电充电倾向并且易于制造。该电荷控制树脂包含一种聚合物作为活性成分，该聚合物具有由以下公式（1）表示的组成单元。在公式（1）中，R1互不相同，可以是氢原子、羟基、卤素原子、含羧基的基团、直链或支链烷基（碳数为1-18）或直链或支链烷氧基（碳数为1-18）；R2可以是氢原子、羟基、卤素原子、含羧基的基团、直链或支链烷基（碳数为1-18）或直链或支链烷氧基（碳数为1-18）；g为1-3的数字；h为1-3的数字；M可以是氢原子、碱金属、直链或支链烷基（碳数为1-18）、铵基或任何这些的混合物。
• Hybrid benzothiazole derived fused triazole/thiazole derivatives as versatile anti-Alzheimer agents: synthesis, characterization, biological evaluation and molecular docking studies
  作者：Shoaib Khan、Rafaqat Hussain、Yousaf Khan、Tayyiaba Iqbal、Sampath Chinnam、Muhammad Akif、Ayed A. Dera

  DOI：10.1016/j.molstruc.2024.139200

  日期：2024.12

  dementia and an increase of 152 million is expected by 2050. This study reports a novel synthetic approach to designing and synthesizing a series of benzothiazole-based fused 1,3,4-triazole/1,3,4-thiadiazole hybrid derivatives (1–19), which show promising potential as therapeutic agents for the treatment of Alzheimer's disease. These derivatives were structurally confirmed through spectroscopic analytical

  据报道，阿尔茨海默病全球有 5000 万人患有痴呆症，预计到 2050 年将增加 1.52 亿。本研究报道了一种新型合成方法，用于设计和合成一系列基于苯并噻唑的熔融 1,3,4-三唑/1,3,4-噻二唑杂化衍生物 （1–19），这些衍生物显示出作为治疗阿尔茨海默病的治疗剂的潜力。这些衍生物通过光谱分析技术进行结构确认，包括 13C NMR、1H NMR 和 HREI-MS。对所有类似物进行针对 AChE 和 BuChE 的生物抑制评价，其中类似物 2 （（IC50 = 3。 30±0.20 和 3.70±0.40 μM）、7（2.70±0.10 和 3.240±0.10 μM）、12（4.80±0.30 和 5.40±0.20 μM）、15（2.10±0.20 和 3.10±0.50 μM）和 19（4.40±0.20 和 5.10±0.10 μM）与标准多奈哌齐（AChE IC50 = 4
• DIHALOGENPROPEN-VERBINDUNGEN, VERFAHREN ZU IHRER HERSTELLUNG, SIE ENTHALTENDE MITTEL UND IHRE VERWENDUNG ALS SCHAEDLINGSBEKAEMPFUNGSMITTEL
  申请人：Bayer CropScience S.A.

  公开号：EP1446375B1

  公开（公告）日：2008-05-14