4-Formylbiphenyl-3-carboxylic acid | 1387557-78-9

• 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-Formylbiphenyl-3-carboxylic acid
• 英文别名: 2-formyl-5-phenylbenzoic acid
• CAS: 1387557-78-9
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: HVWSVVCLWMOMPO-UHFFFAOYSA-N

物化性质

• 沸点：
  445.8±45.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Formylbiphenyl-3-carboxylic acid 在 indium(III) triflate 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-allyl-2-(4-methoxyphenyl)-6-phenylisoindolin-1-one
  参考文献：
  名称：

  异吲哚啉酮和四氢异喹啉的一般催化路线：在（±）-Crispine A合成中的应用

  摘要：

  作为合成不同取代的异吲哚啉酮和四氢异喹啉的一般催化体系，已证明了前所未有的高效路易斯酸催化一锅级联反应。级联作用在一锅中发生一个C–C和两个C–N键形成事件。（±）-crispine A的成功全合成成功地将产品有趣地转化为有价值的合成中间体。

  DOI：

  10.1021/ol502842f
• 作为产物：
  描述：

  苯酞 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 硫酸 、 sodium carbonate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 78.0h， 生成 4-Formylbiphenyl-3-carboxylic acid
  参考文献：
  名称：

  A synthetic route to chiral C(3)-functionalized phthalides via a Ag(I)-catalyzed allylation/transesterification sequence

  摘要：

  A Ag(I)-catalyzed synthesis of chiral C-(3)-substituted phthalides (8a-f) via a Sakurai-Hosomi allylation/transesterification reaction is described (ee <= 86%). A notable feature of this reaction is that it utilizes ortho-substituted aldehydes, which are a class of compounds that generally afford poor levels of stereoinduction when applying most known catalytic asymmetric allylation approaches. It was also found that elongation of the n-alkyl chain length (R-1, up to n=6; R-2=H) of the starting alkyl 2-formylbenzoates (7g-i) improved the enantiomeric excess (ee) of the product. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.002

文献信息

• Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (<i>S</i>)-(−)-3-Butylphthalide
  作者：Haoyi Zhang、Shilei Zhang、Lu Liu、Guangshun Luo、Wenhu Duan、Wei Wang

  DOI：10.1021/jo902118x

  日期：2010.1.15

  enantioenriched “privileged” scaffold. As a result of the sensitive nature of substrate structures of an organocatalytic enantioselective aldol reaction, after extensive optimization of reaction conditions, catalyst l-prolinamide alcohol IV is identified as the best promoter. Interestingly, it is found that in this reaction, addition of an acid additive PhCO2H can significantly enhance reaction efficiency with

  易于构建重要分子框架的有效方法的开发是有机合成的重要目标。手性3-取代的邻苯二甲酸酯广泛分布在大量具有广泛，有效和潜在发展前景的生物活性的天然产物中。在这项研究中，我们发现了2-甲酰基苯甲酸酯与酮/醛的前所未有的有机催化不对称醛醇内酯化反应，可方便地构建对映体富集的“特权”支架。由于有机催化对映选择性醛醇缩合反应的底物结构的敏感性质，在广泛优化反应条件后，催化剂1-脯氨酰胺醇IV被确定为最佳启动子。有趣的是，发现在该反应中，添加酸添加剂PhCO 2 H可以显着提高反应效率，而该方法仅使用低至2.5mol％的IV。此外，由于反应条件对顺序的羟醛-内酯化过程敏感，而又不影响对映选择性和外消旋作用，因此在存在K 2 CO 3的情况下，必须除去催化剂以用于随后的容易的内酯化反应。醛醇内酯化方法是制备具有高对映选择性的合成上和生物学上重要的3-取代的邻苯二甲酸酯的有力方法。报道了3-丁基邻苯二甲酸酯的天然产物的三步催化不对称合成。
• Synthesis of 3-Benzylphthalide Derivatives by Using a TDAE Strategy
  作者：Patrice Vanelle、Maroua Ibrahimi、Omar Khoumeri、Raoudha Abderrahim、Thierry Terme

  DOI：10.1055/a-1290-8349

  日期：2021.2

  A one-pot synthesis of new 3-benzylphthalide derivatives was developed by using a strategy based on tetrakis(dimethylamino)ethylene (TDAE). The reactions in the presence of TDAE of substituted benzyl chlorides with methyl 2-formylbenzoate or of substituted methyl-2-formylbenzoates with 4-nitrobenzyl chloride furnished the corresponding isobenzofuran-1(3H)-one products in moderate to good yields.

  使用基于四（二甲氨基）乙烯 (TDAE) 的策略开发了新型 3-苄基苯酞衍生物的一锅法合成。在 TDAE 存在下，取代苄基氯与 2-甲酰基苯甲酸甲酯或取代 2-甲酰基苯甲酸甲酯与 4-硝基苄基氯的反应以中等至良好的产率提供相应的异苯并呋喃-1(3H)-酮产物。
• A Brønsted acid-catalyzed thioacid addition to <i>in situ</i>-generated aldimine for the synthesis of isoindolinones with the <i>N</i>,<i>S</i>-acetal framework
  作者：Milon M. Sadhu、Chhavi Khajuria、Vinod K. Singh

  DOI：10.1039/d2ob01532c

  日期：——

  A facile methodology was demonstrated for the synthesis of isoindolinones containing the N,S-acetal framework by employing a Brønsted acid catalyst with a three-component reaction. The reaction proceeded via the addition of thioacid to in situ-generated aldimine followed by lactamization, which involved the formation of one C–S bond and two C–N bonds under easily controlled and ambient reaction conditions

  通过使用 Brønsted 酸催化剂进行三组分反应，证明了一种用于合成含有N , S -缩醛骨架的异吲哚啉酮的简便方法。该反应通过将硫代酸添加到原位生成的醛亚胺中，然后进行内酰胺化，这涉及在易于控制和环境反应条件下形成一个 C-S 键和两个 C-N 键。合成了多种取代的异吲哚满酮，收率高达 99%。此外，克级合成和一些有趣的合成转化的演示也证明了这种方法的重要性。
• An Indium-Mediated Allylative/Transesterification DFT-Directed Approach to Chiral C₍₃₎-Functionalized Phthalides
  作者：Roya Mirabdolbaghi、Travis Dudding

  DOI：10.1021/ol301566f

  日期：2012.7.20

  A one-pot synthesis of chiral C-(3)-substituted phthalides via an indium-mediated allylation/transesterification reaction is described. The development of this reaction was facilitated through the applied use of DFT calculations to rationalize the stereoselection of a chiral In-mediated process. It was discovered that the enantiomeric excess of this reaction depended upon the steric size, chain length, and substitution of the aldehyde employed.
• ORGANIC ELECTROLUMESCENCE DEVICE
  申请人：HOSOKAWA Chishio

  公开号：US20100160687A1

  公开（公告）日：2010-06-24

  Materials for organic electroluminescence devices are represented by following general formula [1]: wherein A represents a chrysene group, X 1 to X 4 each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, X 1 and X 2 may be bonded to each other, X 3 and X 4 may be bonded to each other, Y 1 to Y 4 each independently represent an organic group represented by general formula [2], a to d each represent an integer of 0 to 2 and, a+b+c+d≧0; general formula [2] being: wherein R 1 to R 4 each independently represent hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, cyano group or form a triple bond by a linkage of R 1 and R 2 or R 3 and R 4 , Z represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and n represents 0 or 1.