3-(2,3-二氯苯基)丙酸甲酯 | 69426-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2,3-二氯苯基)丙酸甲酯
• 英文名称: methyl 3-(2,3-dichlorophenyl)propionate
• 英文别名: methyl 3-(2,3-dichlorophenyl)propanoate
• CAS: 69426-58-0
• 化学式: C₁₀H₁₀Cl₂O₂
• mdl: MFCD22381368
• 分子量: 233.094
• InChiKey: ZBYOJVCWTWVYRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,3-二氯苯基)丙酸甲酯 在 碳酸氢钠 作用下， 以 sodium hydroxide 为溶剂， 反应 2.0h， 以to yield 3-(2,3-dichlorophenyl)propionic acid的产率得到3-(2,3-二氯苯基)丙酸
  参考文献：
  名称：

  4 AND 5-Halo substituted 2-indanamine compounds

  摘要：

  2-Indanamine化合物具有4和5-卤素取代基，可抑制苯乙醇胺N-甲基转移酶。

  公开号：

  US04128666A1
• 作为产物：
  描述：

  2,3-二氯苯胺 在 氢溴酸 、 溶剂黄146 、 copper(I) bromide 、 锌 、 sodium nitrite 作用下， 反应 1.5h， 生成 3-(2,3-二氯苯基)丙酸甲酯
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007

文献信息

• Systematic Variation of Ligand and Cation Parameters Enables Site-Selective C–C and C–N Cross-Coupling of Multiply Chlorinated Arenes through Substrate–Ligand Electrostatic Interactions
  作者：William A. Golding、Hendrik L. Schmitt、Robert J. Phipps

  DOI：10.1021/jacs.0c11056

  日期：2020.12.30

  related sulfonated phosphine ligands and five bases, each possessing varying cation size, to the challenge of site-selective cross-coupling of multiply chlorinated arenes. The fine tuning provided by these ligand/base combinations is effective for Suzuki-Miyaura coupling and Buchwald-Hartwig coupling on a range of isomeric dichlorinated and trichlorinated arenes, substrates that would produce intractable

  使用配体和底物之间有吸引力的非共价相互作用是控制位置选择性的新兴策略。一个关键问题涉及是否可以使用通常较少定向的静电相互作用来实现对具有多个紧密间隔的反应位置的分子的精细控制。在这里，我们应用了一个由两个密切相关的磺化膦配体和五个碱基组成的 10 件“工具包”，每个碱基都具有不同的阳离子大小，以应对多氯化芳烃的位点选择性交叉偶联的挑战。这些配体/碱基组合提供的微调对于 Suzuki-Miyaura 偶联和 Buchwald-Hartwig 偶联对一系列异构二氯化和三氯化芳烃是有效的，这些底物在使用典型配体时会产生难以处理的混合物。
• Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes
  作者：Fei Yu、Ting Wang、Huan Zhou、Yajun Li、Xinhao Zhang、Hongli Bao

  DOI：10.1021/acs.orglett.7b03244

  日期：2017.12.15

  ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel–Crafts reaction. HOMO–LUMO analysis and

  报道了缺电子（杂）芳烃的非传统铁催化的，邻位优选的自由基烷基化。已显示出各种电子不足的芳烃可与各种伯烷基源反应，以高收率生产烷基化（杂）芳烃。该反应可能是烷基自由基，亲核芳香取代反应，而不是传统的亲电Friedel-Crafts反应。关于区域选择性的关键过渡态的HOMO-LUMO分析和DFT研究与观察到的反应和结论一致。
• 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。
• Indanamines, processes for their preparation and compositions containing them
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0001002B1

  公开（公告）日：1981-08-12
• BONDINELL W. E.; CHAPIN F. W.; GIRARD G. R.; KAISER C.; KROG A. J.; PAVLO+, J. MED. CHEM., 1980, 23, NO 5, 506-511
  作者：BONDINELL W. E.、 CHAPIN F. W.、 GIRARD G. R.、 KAISER C.、 KROG A. J.、 PAVLO+

  DOI：——

  日期：——