3-(2,5-二氯苯基)丙酸 | 68034-76-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(2,5-二氯苯基)丙酸
• 英文名称: 3-(2,5-dichlorophenyl)propanoic acid
• 英文别名: 2.5-Dichlor-hydrozimtsaeure；3-(2,5-dichloro-phenyl)-propionic acid；3-(2,5-Dichlor-phenyl)-propionsaeure；β-(2.5-Dichlor-phenyl)-propionsaeure
• CAS: 68034-76-4
• 化学式: C₉H₈Cl₂O₂
• 分子量: 219.067
• InChiKey: NPCALKBOEAOXNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319

反应信息

• 作为反应物：
  描述：

  3-(2,5-二氯苯基)丙酸 在 三氯化铝 、 氯化亚砜 、 硝酸 作用下， 以 二硫化碳 为溶剂， 反应 76.0h， 生成 4,7-dichloro-2,3-dihydro-6-nitro-1H-inden-1-one
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2
• 作为产物：
  描述：

  1,4-二氯-2-碘苯 在 platinum(IV) oxide palladium diacetate 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 25.0h， 生成 3-(2,5-二氯苯基)丙酸
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2

文献信息

• Benzodiazepine derivatives as inhibitors of gamma secretase
  申请人：——

  公开号：US20040024203A1

  公开（公告）日：2004-02-05

  Compounds of formula (I) are disclosed. The compounds inhibit the action of gamma secretase, and hence find use in the treatment and prevention of Alzheimer's disease.

  公式（I）的化合物被披露。这些化合物抑制γ-分泌酶的作用，因此可用于治疗和预防阿尔茨海默病。
• Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids
  作者：Ji-Tao Yi、Xiang Zhou、Qi-Long Chen、Zhi-Da Chen、Gui Lu、Jiang Weng

  DOI：10.1039/d2cc03221j

  日期：——

  emerging as key structural motifs in organic synthesis, medicinal chemistry, and materials science. Herein we report two efficient and complementary methods for direct decarboxylative fluorosulfonylation of carboxylic acids by the merging of copper catalysis with different N-centered HAT regents. A wide range of structurally diverse sulfonyl fluorides was readily accessed from primary, secondary, and tertiary

  磺酰氟正在成为有机合成、药物化学和材料科学中的关键结构基序。在这里，我们报告了两种有效且互补的方法，通过将铜催化与不同的以N为中心的 HAT 试剂相结合，对羧酸进行直接脱羧氟磺酰化。在温和条件下，一步即可从伯、仲和叔羧酸中轻松获得多种结构多样的磺酰氟。
• Versatile Biocatalytic C(<i>sp</i>³)−H Oxyfunctionalization for the Site‐ Selective and Stereodivergent Synthesis of α‐ and β‐Hydroxy Acids
  作者：Yingle Mao、Weijie Zhang、Zunyun Fu、Yanqiong Liu、Lin Chen、Xin Lian、Dan Zhuo、Jiewei Wu、Mingyue Zheng、Cangsong Liao

  DOI：10.1002/anie.202305250

  日期：2023.8.14

  α-ketoglutarate-dependent aryloxyalkanoate dioxygenases (AADs) are repurposed for applications in biocatalytic oxyfunctionalization. Activity profiling of natural AADs enabled the synthesis of four types of α-and β-hydroxy acids with broad scope, high efficiency, and good selectivity.

  在此，α-酮戊二酸依赖性芳氧基链烷酸双加氧酶（AAD）被重新用于生物催化氧功能化中的应用。天然 AAD 的活性分析使得四种类型的α-和β-羟基酸的合成具有广泛、高效和良好的选择性。
• A new series of potent benzodiazepine γ-secretase inhibitors
  作者：Ian Churcher、Kate Ashton、John W. Butcher、Earl E. Clarke、Timothy Harrison、Huw D. Lewis、Andrew P. Owens、Martin R. Teall、Susie Williams、Jonathan D.J. Wrigley

  DOI：10.1016/s0960-894x(02)00909-5

  日期：2003.1

  A new series of benzodiazepine-containing gamma-secretase inhibitors with potential use in the treatment of Alzheimer's disease is disclosed. Structure-activity relationships of the pendant hydrocinnamate side-chain which led to the preparation of highly potent inhibitors are described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Huisgen,R. et al., Chemische Berichte, 1960, vol. 93, p. 1496 - 1506
  作者：Huisgen,R. et al.

  DOI：——

  日期：——