methyl 4-formyl-[1,1'-biphenyl]-3-carboxylate | 1203589-46-1

• 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: methyl 4-formyl-[1,1'-biphenyl]-3-carboxylate
• 英文别名: 4-Formyl-biphenyl-3-carboxylic acid methyl ester；methyl 2-formyl-5-phenylbenzoate
• CAS: 1203589-46-1
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: TXUIDSIYDQFFMM-UHFFFAOYSA-N

物化性质

• 沸点：
  421.3±45.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-硫代乙内酰脲 、 methyl 4-formyl-[1,1'-biphenyl]-3-carboxylate 在 sodium acetate 、 溶剂黄146 作用下， 反应 4.0h， 以25%的产率得到7-phenyl-3-thioxo-2,3-dihydroimidazo[1,5-b]isoquinoline-1,5-dione
  参考文献：
  名称：

  Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family

  摘要：

  The PIM family of serine/threonine kinases have become an attractive target for anti-cancer drug development, particularly for certain hematological malignancies. Here, we describe the discovery of a series of inhibitors of the PIM kinase family using a high throughput screening strategy. Through a combination of molecular modeling and optimization studies, the intrinsic potencies and molecular properties of this series of compounds was significantly improved. An excellent pan-PIM isoform inhibition profile was observed across the series, while optimized examples show good selectivity over other kinases. Two PIM-expressing leukemic cancer cell lines, MV4-11 and 1(562, were employed to evaluate the in vitro anti-proliferative effects of selected inhibitors. Encouraging activities were observed for many examples, with the best example (44) giving an IC55 of 0.75 mu M against the K562 cell line. These data provide a promising starting point for further development of this series as a new cancer therapy through PIM kinase inhibition. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.056
• 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 、 potassium 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 82.0h， 生成 methyl 4-formyl-[1,1'-biphenyl]-3-carboxylate
  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。
• Unified Approach to Isoindolinones and THIQs via Lewis Acid Catalyzed Domino Mukaiyama–Mannich Lactamization/Alkylations: Application in the Synthesis of (±)-Homolaudanosine
  作者：Sivasankaran Dhanasekaran、Anirban Kayet、Arun Suneja、Vishnumaya Bisai、Vinod K. Singh

  DOI：10.1021/acs.orglett.5b01197

  日期：2015.6.5

  variety of isoindolinones and tetrahydroisoquinolines via a Lewis acid catalyzed domino Mukaiyama–Mannich lactamization/alkylation is achieved. This transformation comprises a sequential formation of three new bonds through a one-pot, three-component procedure to afford product in moderate to high yields. A concise synthesis of (±)-homolaudanosine (2b) has been achieved using this method.

  通过路易斯酸催化的多米诺山Mukaiyama–Mannich内酰胺化/烷基化反应，可以实现新颖而有效的多种异吲哚啉酮和四氢异喹啉的合成。这种转变包括通过一锅三组分程序依次形成三个新的键，以提供中等至高收率的产物。使用此方法已实现了（±）-高麦芽糖苷（2b）的简明合成。
• A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (<i>S</i>)-PD 172938
  作者：Sumit K. Ray、Milon M. Sadhu、Rayhan G. Biswas、Rajshekhar A. Unhale、Vinod K. Singh

  DOI：10.1021/acs.orglett.8b03597

  日期：2019.1.18

  have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

  分别通过串联曼尼希内酰胺化和醛醇内酯化反应完成了手性布朗斯台德酸催化的异吲哚啉酮和邻苯二甲酸酯的对映选择性合成。以优异的收率提供了多种富含对映体的异吲哚啉酮（ee含量高达99％）和邻苯二甲酸酯（ee含量高达85％）。此外，已经通过使用该方案证明了（S）-PD 172938的简明合成。
• Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations
  作者：Sivasankaran Dhanasekaran、Arun Suneja、Vishnumaya Bisai、Vinod K. Singh

  DOI：10.1021/acs.orglett.5b03331

  日期：2016.2.19

  A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of tetrahydroisoquinolines (THIQs) in high yields.

  据报道，一锅，三组分合成的广泛取代的异吲哚啉酮和异喹啉酮具有路易斯酸催化的有效斯特雷克反应和内酰胺化顺序，可提供高至高收率的产物。该方法还扩展到高产率合成四氢异喹啉（THIQs）。
• 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。