(1,1':2',1''-terphenyl)-4'-carbaldehyde | 61283-03-2

• 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: (1,1':2',1''-terphenyl)-4'-carbaldehyde
• 英文别名: 3,4-diphenylbenzaldehyde；[1,1':2',1''-Terphenyl]-4'-carboxaldehyde
• CAS: 61283-03-2
• 化学式: C₁₉H₁₄O
• 分子量: 258.32
• InChiKey: BSCNXGBEMRVZRE-UHFFFAOYSA-N

物化性质

• 沸点：
  399.2±31.0 °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：

  (1,1':2',1''-terphenyl)-4'-carbaldehyde 在 palladium on activated charcoal 氢气 、 sodium methylate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl 2-{3-[2-(3,4-diphenylphenyl)ethan-1-yl]phenoxy}acetate
  参考文献：
  名称：

  Miyamae, Tetsuhisa; Hashizume, Hirokazu; Ogawa, Tadashi, Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 1, p. 13 - 18

  摘要：

  DOI：
• 作为产物：
  描述：

  o-terphenyl-4'-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 生成 (1,1':2',1''-terphenyl)-4'-carbaldehyde
  参考文献：
  名称：

  Miyamae, Tetsuhisa; Hashizume, Hirokazu; Ogawa, Tadashi, Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 1, p. 13 - 18

  摘要：

  DOI：

文献信息

• AROMATIC COMPOUNDS HAVING SPHINGOSINE-1-PHOSPHONATE (S1P) RECEPTOR ACTIVITY
  申请人：Takeuchi Janet A.

  公开号：US20110281822A1

  公开（公告）日：2011-11-17

  Novel aromatic compounds which are useful as sphingosine-1-phosphate modulators and useful for treating a wide variety of disorders associated with modulation of sphingosine-1-phosphate receptors.

  一种新颖的芳香化合物，可用作神经酰胺-1-磷酸酯调节剂，对治疗与神经酰胺-1-磷酸酯受体调节相关的各种疾病有益。
• UV-Promoted Metal- and Photocatalyst-Free Direct Conversion of Aromatic Aldehydes to Nitriles
  作者：F. Joy、F. Peter、P. C. Gokul、A. Nizam、S. Chinnam

  DOI：10.1134/s1070428022030174

  日期：2022.3

  UV-induced functional group transformation of aromatic aldehydes to nitriles has been reported. The developed strategy delivers various functionalized aromatic nitriles with high yields and purity. The UV irradiation activates the carbonyl group of aldehydes and leads to the formation of aldoxime intermediate, further resulting in the generation of nitriles. The striking highlights of the reported methodology

  摘要 已经报道了一种有效、简单且无催化剂的紫外诱导的芳香醛向腈的官能团转化。开发的策略以高收率和纯度提供了各种功能化的芳族腈。紫外线照射激活醛的羰基并导致醛肟中间体的形成，进一步导致腈的产生。所报道的方法的显着亮点是简单的反应条件、良好的收率、UV 促进的转化和无催化剂合成。由于上述优点，该方法为环境友好的化学合成提供了有力的支持。
• Novel Estrogen Receptor Ligands Based on an Anthranylaldoxime Structure:  Role of the Phenol-Type Pseudocycle in the Binding Process
  作者：Filippo Minutolo、Michela Antonello、Simone Bertini、Gabriella Ortore、Giorgio Placanica、Simona Rapposelli、Shubin Sheng、Kathryn E. Carlson、Benita S. Katzenellenbogen、John A. Katzenellenbogen、Marco Macchia

  DOI：10.1021/jm0308390

  日期：2003.9.1

  pseudocycle A' in the binding process was confirmed by the fact that benzaldoxime 4 showed a greatly reduced binding affinity compared to salicylaldoxime 1. Moreover, the binding affinity improved considerably when the A'-ring contained either an unsubstituted nitrogen (5a) or an N-Me group (5b). On the other hand, the N-Et-substituted anthranyl derivative 5c showed a marked drop in binding affinity. Molecular

  3,4-二苯基水杨醛肟系统1是具有异常结构的雌激素受体（ER）配体，具有氢键键合的伪环A'环代替大多数雌激素所特有的典型酚A环。我们已经通过制备3,4-二苯基苯甲恶肟（4）来研究伪环A'在与ER结合中的作用，该化合物完全没有该环，但仍然保留了原始分子1的所有其他特征。作为一系列3,4-二苯基蒽基醛肟（5a-c），其中参与形成假环A'的杂原子的性质已从氧（1）变为未被取代（5a）或被取代的氮带有小的烷基（5b中的甲基或5c中的乙基）。氢键假环A'的重要性 与水杨醛肟1相比，苯甲醛肟4的结合亲和力大大降低，这证实了结合过程中的亲和力。此外，当A'环含有未取代的氮（5a）或N-Me基团时，结合亲和力大大提高。 （5b）。另一方面，N-Et-取代的蒽基衍生物5c显示出结合亲和力的显着下降。在ERalpha上进行的分子模型对接研究证实，化合物5a和5b很好地适合于配体结合袋，对5b的N-Me组来说特
• Development of terphenyl-2-methyloxazol-5(4<i>H</i>)-one derivatives as selective reversible MAGL inhibitors
  作者：Carlotta Granchi、Isabella Caligiuri、Eleonora Bertelli、Giulio Poli、Flavio Rizzolio、Marco Macchia、Adriano Martinelli、Filippo Minutolo、Tiziano Tuccinardi

  DOI：10.1080/14756366.2017.1375484

  日期：2017.1.1

  Monoacylglycerol lipase is a serine hydrolase that plays a major role in the degradation of the endocannabinoid neurotransmitter 2-arachidonoylglycerol. A wide number of MAGL inhibitors are reported in literature; however, many of them are characterised by an irreversible mechanism of action and this behavior determines an unwanted chronic MAGL inactivation, which acquires a functional antagonism of the endocannabinoid system. The possible use of reversible MAGL inhibitors has only recently been explored, due to the lack of known compounds possessing efficient reversible inhibitory activities. In this work, we report a new series of terphenyl-2-methyloxazol-5(4H)-one derivatives characterised by a reversible MAGL-inhibition mechanism. Among them, compound 20b showed to be a potent MAGL reversible inhibitor (IC50=348nM) with a good MAGL/FAAH selectivity. Furthermore, this compound showed antiproliferative activities against two different cancer cell lines that overexpress MAGL.
• US8513220B2
  申请人：——

  公开号：US8513220B2

  公开（公告）日：2013-08-20