4-chloro-4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid

• 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: 4-chloro-4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid
• 英文别名: 5-Chloro-2-(4-methoxyphenyl)benzoic acid
• 化学式: C₁₄H₁₁ClO₃
• mdl: MFCD11933661
• 分子量: 262.693
• InChiKey: CNRBOKUTNVPZOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以83%的产率得到8-chloro-3-methoxy-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Oxidant-Free C(sp²)–H Functionalization/C–O Bond Formation: A Kolbe Oxidative Cyclization Process

  摘要：

  An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H-2 being the only byproduct. A series of dibenzopyranones was obtained in good to excellent yields. Urolithins A, B, and C are formally synthesized by adopting this method as a key step to demonstrate its synthetic utility.

  DOI：

  10.1021/acs.joc.8b00089
• 作为产物：
  描述：

  4-碘苯甲醚 、 3-氯苯甲酸 在 palladium diacetate 、 caesium carbonate 、 N-acetyl-L-isoleucine 、 silver carbonate 作用下， 反应 36.0h， 以70%的产率得到4-chloro-4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid
  参考文献：
  名称：

  Ambient-Temperature Ortho C–H Arylation of Benzoic Acids with Aryl Iodides with Ligand-Supported Palladium Catalyst

  摘要：

  The ambient-temperature ortho C-H arylation of electron-deficient benzoic acids with aryl iodides has been achieved by using an Ac-Ile-OH-supported Pd catalyst. A wide range of unactivated benzoic adds could cross-couple an array of aryl iodides in moderate to excellent yields: The choice of HFIP as a solvent is crucial to realizing the mild C-H arylation;, and the beneficial effect of the ligand on the reaction likely stems from the accelerated C-H activation process and the improved catalyst lifetime.

  DOI：

  10.1021/acs.orglett.5b01398

文献信息

• Dual-role catalysis of iridium in photo-irradiation synthesis of 9-fluorenone through intramolecular cyclization <i>via</i> hydrogen evolution
  作者：Xi Hong、Yi-Wen Zhang、Bing Zhan、Xue-Juan Chen、De-Jun Hu、Zhi-Ming Li、Xiu-Feng Hou

  DOI：10.1039/d3cy01353g

  日期：——

  the dehydrogenation. The catalyst [Ir(Fmpbo)2dtbppy]PF6 played a dual role as both the photoredox catalyst to initiate the benzoyl radical reaction and the TM catalyst to finish the aromatization and the hydrogen evolution. The photoredox/TM dual catalytic role of the Ir catalyst was proposed firstly. The reactions provide good to excellent yields of the products under mild and economic conditions.

  以2-芳基苯并[ d ]恶唑基铱配合物为双用途催化剂，由[1,1'-联苯]-2-羧酸光氧化还原催化合成9-芴酮。首次发现了伴随 9-芴酮形成的不寻常的析氢反应。形成的氢的量与9-芴酮成正比，这使得反应原子经济。结合DFT计算，提出了铱催化剂的配体解离过程来解释脱氢反应。催化剂[Ir(Fmpbo) 2 dtbppy]PF 6发挥双重作用，既作为引发苯甲酰自由基反应的光氧化还原催化剂，又作为完成芳构化和析氢的TM催化剂。首次提出Ir催化剂的光氧化还原/TM双重催化作用。该反应在温和且经济的条件下提供了良好至优异的产物收率。
• Oxidant-Free C(sp²)–H Functionalization/C–O Bond Formation: A Kolbe Oxidative Cyclization Process
  作者：Lei Zhang、Zhenxing Zhang、Junting Hong、Jian Yu、Jianning Zhang、Fanyang Mo

  DOI：10.1021/acs.joc.8b00089

  日期：2018.3.16

  An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H-2 being the only byproduct. A series of dibenzopyranones was obtained in good to excellent yields. Urolithins A, B, and C are formally synthesized by adopting this method as a key step to demonstrate its synthetic utility.
• Ambient-Temperature Ortho C–H Arylation of Benzoic Acids with Aryl Iodides with Ligand-Supported Palladium Catalyst
  作者：Changlei Zhu、Yuanfei Zhang、Jian Kan、Huaiqing Zhao、Weiping Su

  DOI：10.1021/acs.orglett.5b01398

  日期：2015.7.17

  The ambient-temperature ortho C-H arylation of electron-deficient benzoic acids with aryl iodides has been achieved by using an Ac-Ile-OH-supported Pd catalyst. A wide range of unactivated benzoic adds could cross-couple an array of aryl iodides in moderate to excellent yields: The choice of HFIP as a solvent is crucial to realizing the mild C-H arylation;, and the beneficial effect of the ligand on the reaction likely stems from the accelerated C-H activation process and the improved catalyst lifetime.