3,5-diphenylbenzaldehyde | 220955-80-6

• 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: 3,5-diphenylbenzaldehyde
• 英文别名: [1,1':3',1''-terphenyl]-5'-carbaldehyde；[1,1';3',1'']Terphenyl-5'-carbaldehyde
• CAS: 220955-80-6
• 化学式: C₁₉H₁₄O
• 分子量: 258.32
• InChiKey: ABFOUYGCEANIRV-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97.5 °C
• 沸点：
  441.9±34.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-diphenylbenzaldehyde 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.58h， 生成 1-(溴甲基)-3,5-二苯基苯
  参考文献：
  名称：

  Optimization and Structure–Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides

  摘要：

  The oxytocinase subfamily of M1 aminopeptidases, Consisting of ER aminopeptidase 1 (ERAP1), ER aminopeptidase 2 (ERAP2), and insulin-regulated aminopeptidase (IRAP), plays critical roles in the generation of antigenic peptides and indirectly regulates human adaptive immune responses. We have previously,demonstrated that phosphinic pseudotripeptides can constitute potent inhibitors of this group of enzymes. In this study, we used synthetic methodologies able to furnish a series of stereochemically defined phosphinic pseudotripeptides and demonstrate that side chains at P-1' and P-2' positions are Critical determinants in driving potency and selectivity. We identified low nanomolar inhibitors of ERAP2 and IRAP that display selectivity of more than 2 and 3 orders of magnitude, respectively. Cellular analysis demonstrated that one of the compounds that is a selective IRAP inhibitor can reduce IRAP-dependent but not, ERAP1-dependent cross-presentation by dendritic cells with nanomolar efficacy. Our results encourage further preclinical development of phosphinic pseudotripeptides as regulators of adaptive immune responses.

  DOI：

  10.1021/acs.jmedchem.6b01031
• 作为产物：
  描述：

  2,4,6-三溴苯胺 在 盐酸 、 magnesium 、 1,2-二溴乙烷 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 3,5-diphenylbenzaldehyde
  参考文献：
  名称：

  A Practical and Efficient Synthesis of 5′-Substituted m-Terphenyls

  摘要：

  下面概述了一种简单、便捷、可扩展的合成方法，用于从市售原料制备多种5′-取代的m-三联苯化合物。基于m-三联苯骨架，生成了一系列新颖化合物。此外，我们还提供了3,5-二苯基苯甲醛（1,1′:3′,1′′-三联苯-5′-甲醛）的全面完整表征，包括晶体结构。

  DOI：

  10.1055/s-2007-983722

文献信息

• Nanocrystalline Titania-Supported Palladium(0) Nanoparticles for Suzuki-Miyaura Cross-Coupling of Aryl and Heteroaryl Halides
  作者：B. Sreedhar、Divya Yada、P. Surendra Reddy

  DOI：10.1002/adsc.201100012

  日期：2011.10

  The Suzuki cross-coupling reaction of various aryl and heteroaryl halides with arylboronic and heteroarylboronic acids was studied using a titania-supported palladium(0) catalyst at room temperature under air. The conversion and selectivity results obtained for many substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The methodology is similarly effective

  使用二氧化钛负载的钯（0）催化剂在室温下于空气中研究了各种芳基和杂芳基卤化物与芳基硼酸和杂芳基硼酸的Suzuki交叉偶联反应。对于许多底物，获得的转化率和选择性结果极好，与活性更高甚至均相的催化剂所提供的结果相似。使用2-溴-3,4,5-三甲氧基苯甲醛作为偶合伙伴，该方法同样有效，并获得了高收率的产品。此外，已表明其可用于合成三联苯和四联苯。通过简单的过滤从反应中定量回收催化剂，并重复使用多个循环，而活性没有明显损失。
• Cellulose Schiff base-supported Pd(II): An efficient heterogeneous catalyst for Suzuki Miyaura cross-coupling
  作者：P. S. Pharande、G. S. Rashinkar、D. M. Pore

  DOI：10.1007/s11164-021-04528-1

  日期：2021.11

  Cellulose-supported Schiff base Pd(II) complex [(Cell-Sc-Pd(II))] has been designed and synthesized by multistep approach. (Cell-Sc-Pd(II)) was characterized by techniques, viz. FT-IR, XRD, XPS, EDS, FE-SEM and TGA. Catalytic activity of (Cell-Sc-Pd(II)) is explored for Suzuki Miyaura cross-coupling of phenyl boronic acid and aryl halides. Special features of present method are high TONs and TOFs,

  纤维素支持的希夫碱 Pd(II) 复合物 [(Cell-Sc-Pd(II))] 已通过多步方法设计和合成。(Cell-Sc-Pd(II)) 的特点是技术，即。FT-IR、XRD、XPS、EDS、FE-SEM 和 TGA。探索了 (Cell-Sc-Pd(II)) 的催化活性，用于苯基硼酸和芳基卤化物的 Suzuki Miyaura 交叉偶联。本方法的特点是高 TONs 和 TOFs、低催化剂负载（0.0016 mol%）、催化剂至少可重复使用五次以及合成新的呫吨联苯衍生物。 图形摘要
• Suzuki–Miyaura Cross-Couplings under Acidic Conditions
  作者：Lucas Pruschinski、Ana-Luiza Lücke、Tyll Freese、Sean-Ray Kahnert、Sebastian Mummel、Andreas Schmidt

  DOI：10.1055/s-0039-1691487

  日期：2020.3

  Pd(PPh3)4 have been carried out using lithium N-phenylsydnone-4-carboxylate as additive, which gave best yields at pH 5.7 in a mixture of acetic acid, water, and sodium carbonate. Reaction parameters such as the Pd source, the solvent, reaction time and temperature, acid, base and carboxylate have been varied and some representative examples of the Suzuki–Miyaura reaction have been examined.

  使用N-苯基亚砜基-4-羧酸锂作为添加剂进行了Pd（PPh 3）4的Suzuki-Miyaura反应，在乙酸，水和碳酸钠的混合物中，pH值为5.7时，产率最高。反应参数（例如Pd来源，溶剂，反应时间和温度，酸，碱和羧酸盐）已发生变化，并且对Suzuki-Miyaura反应的一些代表性实例进行了研究。
• Synthesis of Substituted Benzaldehydes via a Two-Step, One-Pot Reduction/Cross-Coupling Procedure
  作者：Dorus Heijnen、Hugo Helbert、Gert Luurtsema、Philip H. Elsinga、Ben L. Feringa

  DOI：10.1021/acs.orglett.9b01274

  日期：2019.6.7

  The synthesis of functionalized (benz)aldehydes, via a two-step, one-pot procedure, is presented. The method employs a stable aluminum hemiaminal as a tetrahedral intermediate, protecting a latent aldehyde, making it suitable for subsequent cross-coupling with (strong nucleophilic) organometallic reagents, leading to a variety of alkyl and aryl substituted benzaldehydes. This very fast methodology

  介绍了通过两步一锅法合成官能化（苯）醛的方法。该方法使用稳定的半铝铝作为四面体中间体，保护潜在的醛，使其适合于随后与（强亲核性）有机金属试剂交叉偶联，从而生成各种烷基和芳基取代的苯甲醛。这种非常快速的方法还有助于11 C放射性标记醛的有效合成。铝酸盐配合物可将烷基片段金属转移到钯上，然后进行交叉偶联。
• A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids
  作者：Jianfeng Chen、Junyu Zhao、Xing Gong、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2016.09.005

  日期：2016.10

  A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee’s under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines

  通过多步合成已经开发了一种新型的带有相邻手性立体中心的手性吡ido胺。吡ido胺在非常温和的条件下，在α-酮酸的不对称转氨反应中显示出催化活性，从而以27-78％的产率提供了34-62％ee的多种光学活性氨基酸。这项工作提供了使用溴吡啶7作为关键合成子来构建新的手性吡ido胺的合成策略，也代表了手性吡x胺在不对称催化中的早期应用实例。