4-(3,4-二甲基苯基)苯甲酸甲酯 | 647842-33-9

• 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: 4-(3,4-二甲基苯基)苯甲酸甲酯
• 英文名称: methyl 3',4'-dimethyl-[1,1'-biphenyl]-4-carboxylate
• 英文别名: Methyl 3',4'-dimethyl[1,1'-biphenyl]-4-carboxylate；methyl 4-(3,4-dimethylphenyl)benzoate
• CAS: 647842-33-9
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: RVWULOQKYNEQIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  100.7-100.9 °C
• 沸点：
  361.9±21.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  4-(3,4-二甲基苯基)苯甲酸甲酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以50%的产率得到3,4-二甲基联苯-4-羧酸
  参考文献：
  名称：

  Biphenylcarboxamide derivatives as antagonists of platelet-activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl]-1,1'-biphenyl-4-carboxamides was prepared, and the compounds were evaluated for platelet-activating factor (PAF) antagonist activity in a binding assay employing washed, whole dog platelets and in vivo for their ability to inhibit PAF-induced bronchoconstriction in the guinea pig. The inclusion of a methyl group in the R configuration on the side-chain carbon adjacent to the carboxamide nitrogen atom of these derivatives resulted in a marked enhancement of potency in the binding assay for compounds unsubstituted in the biphenyl 2-position and, more importantly, in improved oral bioavailability. Previous work with related pyrido[2,1-b]-quinazoline-8-carboxamides suggests that the presence of such an alkyl group improves bioavailability by rendering the resulting compounds resistant to degradation by liver amidases. The most interesting compounds to emerge from this work are (R)-2-bromo-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl]-1,1'-bi phe nyl- 4-carboxamide (33) and (R)-2-butyl-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl]- 1,1'-biphenyl-4-carboxamide (40) each of which inhibits PAF-induced bronchoconstriction in the guinea pig by greater than 55%. 6 h after an oral dose of 50 mg/kg.

  DOI：

  10.1021/jm00128a025
• 作为产物：
  描述：

  邻二甲苯 、 4-甲氧羰基苯硼酸 在 silver hexafluoroantimonate 、 六氟异丙醇 、 N-氟代双苯磺酰胺 、 N,N-二甲基甲酰胺 、 palladium dichloride 作用下， 以 水 为溶剂， 反应 24.0h， 以80%的产率得到4-(3,4-二甲基苯基)苯甲酸甲酯
  参考文献：
  名称：

  Amide-Ligand-Controlled Highly para-Selective Arylation of Monosubstituted Simple Arenes with Arylboronic Acids

  摘要：

  Pd-catalyzed highly para-selective arylations of monosubstituted simple arenes with arylboronic acids to widely existed biaryls have been developed. Inspired by requisite amide-directing groups in reported selective oxidative couplings, amide ligands, especially DMF, are designed and found to be critical for the selectivity control in current arylations.

  DOI：

  10.1021/jacs.6b12907

文献信息

• Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls
  作者：Ren-Jin Tang、Qing He、Luo Yang

  DOI：10.1039/c4cc10155c

  日期：——

  A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the

  开发了芳香醛与富电子或缺电子的芳烃的无金属氧化脱羰基偶联剂，以生产联芳基化合物。基于底物范围，邻位区域选择性，自由基捕获实验和DFT计算研究，提出了通过非链自由基均相芳香族取代（HAS）类型的机理进行这种新型偶联。随着芳香醛和芳烃的现成可用，无金属条件应使这种偶联对于联芳基合成具有吸引力。
• <i>meta</i> ‐Selective C−H Arylation of Fluoroarenes and Simple Arenes
  作者：Luo‐Yan Liu、Jennifer X. Qiao、Kap‐Sun Yeung、William R. Ewing、Jin‐Quan Yu

  DOI：10.1002/anie.202002865

  日期：2020.8.10

  to promote ortho‐C−H metalation. Based upon this reactivity, we employed an activated norbornene that traps the ortho‐palladation intermediate and is then relayed to the meta position, leading to meta‐selective C−H arylation of fluoroarenes. Deuterium experiment suggests that this meta‐arylation is initiated by ortho C−H activation and the catalytic cycle is terminated by C‐2 protonation. A dual‐ligand

  已知氟可促进邻位‐C−H 金属化。基于这种反应性，我们采用了一种活化的降冰片烯来捕获邻位钯化中间体，然后转移到间位，从而导致氟芳烃的间位选择性C−H 芳基化。氘实验表明，这种元芳基化是由邻位C-H 激活引发的，催化循环由 C-2 质子化终止。双配体系统对于观察到的高反应性和位点选择性至关重要。将这种方法应用于简单的苯或其他芳烃也可以提供具有良好收率和位点选择性的芳基化产物。
• OXYNTOMODULIN ANALOGS AND METHODS OF MAKING AND USING SAME
  申请人：The Research Foundation for The State University of New York

  公开号：US20170196940A1

  公开（公告）日：2017-07-13

  Provided are oxyntomodulin analogs. The peptide analogs have at least two cysteines. The two cysteines are separated by six amino acids such that they can be crosslinked using suitable crosslinking moieties. The crosslinked peptides have long half-lives and/or efficacy. For example, peptide analog compositions are used for inducing weight loss and/or reducing blood glucose levels.

  提供的是氧子脱氨酮素类似物。这些肽类似物至少含有两个半胱氨酸。这两个半胱氨酸之间相隔六个氨基酸，使它们可以通过适当的交联基团进行交联。交联的肽具有较长的半衰期和/或疗效。例如，肽类似物组合用于诱导减重和/或降低血糖水平。
• LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates
  作者：Liangbin Huang、Laura K. G. Ackerman、Kai Kang、Astrid M. Parsons、Daniel J. Weix

  DOI：10.1021/jacs.9b05461

  日期：2019.7.17

  While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy

  尽管联芳基化合物的合成在过去几十年中取得了迅速进展，但最丰富的芳基亲电试剂——芳基氯的交叉乌尔曼偶联仍然难以捉摸。这里报道了芳基氯与芳基三氟甲磺酸酯的第一个通用交叉乌尔曼偶联反应。使用多金属策略和适当选择的添加剂可以克服与惰性亲电试剂与反应性亲电试剂偶联相关的选择性挑战。研究表明，LiCl 通过加速 Ni(II) 还原为 Ni(0) 并抵消 Zn(II) 盐对 Zn(0) 还原的自抑制，对于有效交叉偶联至关重要。修改后的条件可耐受任一偶联配偶体上的各种官能团（42 个示例），示例包括氟比洛芬的三步合成。
• Borenium-Ion-Catalyzed C–H Borylation of Arenes
  作者：Xinyue Tan、Xi Wang、Zhen Hua Li、Huadong Wang

  DOI：10.1021/jacs.2c12151

  日期：2022.12.28

  Non-metal-catalyzed C–H borylation of arenes represents a sustainable and environment-friendly approach for the functionalization of arenes. Despite its promise as an alternative to traditional transition-metal systems, its substrate scope is generally limited to electron-rich arenes, thus hindering its application in organic synthesis. Herein, we report the development of a borenium-ion catalyst which

  芳烃的非金属催化 C-H 硼化代表了一种可持续且环境友好的芳烃功能化方法。尽管它有望替代传统的过渡金属体系，但其底物范围通常仅限于富电子芳烃，因此阻碍了其在有机合成中的应用。在此，我们报告了一种硼离子催化剂的开发，该催化剂可以在环境条件下使用 4-氯儿茶酚硼烷 (HBcat Cl ) 作为硼酸化试剂对未活化的芳烃进行硼酸化。这种无金属催化体系适用于空间位阻位置 C-H 键的硼化，这对过渡金属体系来说一直是一项具有挑战性的任务。此外，该催化系统允许对-酚类的选择性一锅硼化，这尚未通过使用过渡金属系统实现。我们的机理研究和计算研究支持芳烃底物和硼离子催化剂对 H-Bcat Cl键的协同活化。这会生成 Wheland 中间体和中性氢硼烷物质，然后 Wheland 中间体与氢硼烷物质发生去质子化。C-H 键断裂的后一步可能是限速步骤。