6-methoxy-biphenyl-2-carbaldehyde | 151038-65-2

• 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: 6-methoxy-biphenyl-2-carbaldehyde
• 英文别名: [1,1'-Biphenyl]-2-carboxaldehyde, 6-methoxy-；3-methoxy-2-phenylbenzaldehyde
• CAS: 151038-65-2
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: UYBCQXZXPIRFKX-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±30.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  6-methoxy-biphenyl-2-carbaldehyde 在 双氧水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以798 mg的产率得到3-methoxy-2-phenylbenzoic acid
  参考文献：
  名称：

  Exploration of Biaryl Carboxylic Acids as Proton Shuttles for the Selective Functionalization of Indole C–H Bonds

  摘要：

  A survey of diversely substituted 2-arylbenzoic acids were synthesized and tested for use as proton shuttle in the direct arylation of indoles with bromobenzenes. It was found that 3-ethoxy-2-phenylbenzoic acid gives superior yield and selectivity for this class of substrates.

  DOI：

  10.1021/acs.joc.8b00417
• 作为产物：
  描述：

  2-溴-3-羟基苯甲醛 在 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 、 palladium diacetate 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 6-methoxy-biphenyl-2-carbaldehyde
  参考文献：
  名称：

  Exploration of Biaryl Carboxylic Acids as Proton Shuttles for the Selective Functionalization of Indole C–H Bonds

  摘要：

  A survey of diversely substituted 2-arylbenzoic acids were synthesized and tested for use as proton shuttle in the direct arylation of indoles with bromobenzenes. It was found that 3-ethoxy-2-phenylbenzoic acid gives superior yield and selectivity for this class of substrates.

  DOI：

  10.1021/acs.joc.8b00417

文献信息

• 4-苄基氨基苯磺酰胺类衍生物、及其制备和用途
  申请人：武汉赛莱亚生物科技有限公司

  公开号：CN111518053B

  公开（公告）日：2023-03-14

  本发明提供了一种式(I)
• Compounds and Methods for Catalytic Directed ortho Substitution of Aromatic Amides and Esters
  申请人：Zhao Yigang

  公开号：US20120302752A1

  公开（公告）日：2012-11-29

  Methods are described for efficient and regioselective reactions that are Ru-catalyzed and either (i) amide-directed C—H, C—N, C—O activation/C—C bond forming reactions, (ii) ester-directed C—O and C—N activation/C—C bond forming reactions, or (iii) amide-directed C—O activation/hydrodemethoxylation reactions. All of these reactions of directed C—H, C—N, C—O activation/coupling reactions establish a catalytic base-free DoM-cross coupling process at non-cryogenic temperature. High regioselectivity, yields, operational simplicity, low cost, and convenient scale-up make these reactions suitable for industrial applications. Many previously unknown amide-substituted or ester-substituted aryl and heteroaryl compounds are presented with synthetic details also provided.

  描述了一种高效和区域选择性反应的方法，这些反应是以钌为催化剂的，可以是（i）酰胺导向的C—H、C—N、C—O活化/C—C键形成反应，（ii）酯导向的C—O和C—N活化/C—C键形成反应，或者（iii）酰胺导向的C—O活化/脱甲氧基反应。所有这些导向C—H、C—N、C—O活化/偶联反应在非低温下建立了一个无催化剂碱的DoM-交叉偶联过程。高区域选择性、产率、操作简便、低成本和便于放大规模使得这些反应适用于工业应用。还提供了许多以前未知的酰胺取代或酯取代的芳基和杂环芳基化合物，同时提供了合成细节。
• Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
  作者：W. Michael Seganish、Philip DeShong

  DOI：10.1021/jo035309q

  日期：2004.2.1

  Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant

  五价芳基和杂芳基双（邻苯二酚）硅酸盐在氟化物源的存在下与芳基和杂芳基三氟甲磺酸酯进行钯催化的交叉偶联，收率很高。这些固体，空气稳定的双（邻苯二酚）硅酸盐是在胺碱的存在下，由邻苯二酚和芳基硅氧烷之间的高产率置换反应制备的。交叉偶联反应可耐受广泛的供电子基团和吸电子基团。将二邻位取代的三氟甲磺酸酯的几个实例成功地与这些试剂偶联。
• Regio- and Chemoselective Kumada–Tamao–Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions
  作者：Xuefeng Cong、Huarong Tang、Xiaoming Zeng

  DOI：10.1021/jacs.5b08621

  日期：2015.11.18

  the cross-coupling reactions with aryl ethers via C-O bond activation have attracted broad interest. However, the functionalizations of C-O bonds are mainly limited to nickel catalysis, and selectivity has long been a prominent challenge when several C-O bonds are present in the one molecule. We report here the first chromium-catalyzed selective cross-coupling reactions of aryl ethers with Grignard reagents

  作为一种环境友好的合成工具，通过 CO 键活化与芳基醚的交叉偶联反应引起了广泛的兴趣。然而，CO 键的功能化主要限于镍催化，当一个分子中存在多个 CO 键时，选择性一直是一个突出的挑战。我们在这里报告了第一个铬催化的芳基醚与格氏试剂通过 CO（烷基）键断裂的选择性交叉偶联反应。在室温下使用简单、廉价的铬 (II) 预催化剂结合亚氨基助剂实现了多种转化。它为高效和选择性地构建官能化芳香醛提供了新途径。
• Chromium-Catalyzed, Regioselective Cross-Coupling of C–O Bonds by Using Organic Bromides as Reactants
  作者：Meiming Luo、Xiaoming Zeng、Jinghua Tang

  DOI：10.1055/s-0036-1588568

  日期：2017.12

  cross-coupling of C–O bonds with widely accessible organic bromides as reactants for the preparation of ortho-arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

  我们报告了铬催化的 C-O 键与可广泛使用的有机溴化物作为反应物在室温下制备邻芳基化或烷基化芳香醛的交叉偶联。金属镁的使用对于反应的发生来说是必不可少的，这使它比以前的反应具有优势，这些反应涉及必须在偶联前与有机卤化物分开制备的格氏试剂。