(4-氯-2-甲酰基苯基)乙酸酯 | 60315-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (4-氯-2-甲酰基苯基)乙酸酯
• 英文名称: 2-acetoxy-5-chlorobenzaldehyde
• 英文别名: 4-chloro-2-formylphenyl acetate；(4-chloro-2-formylphenyl) acetate
• CAS: 60315-73-3
• 化学式: C₉H₇ClO₃
• 分子量: 198.606
• InChiKey: KXWQJKOWGGPRQB-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  303.0±32.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (4-氯-2-甲酰基苯基)乙酸酯 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 (5-Chloro-2-hydroxyphenyl)methyl acetate
  参考文献：
  名称：

  铜（I）催化的加氢烷氧基化/氢键合诱导的不对称杂Diels-Alder环加成级联反应：芳族螺缩酮的一种方法

  摘要：

  一件事导致另一件事：可以通过有效的级联过程，包括前所未有的Cu I催化的分子内炔烃加氢烷氧基化和不对称杂Diels-Alder环加成反应，构建双（苯甲酰化）5,6-螺酮骨架。该方法可从两种容易获得的开链起始原料中以高收率和出色的非对映选择性产生一系列功能多样的螺缩酮。

  DOI：

  10.1002/asia.201101056
• 作为产物：
  描述：

  1,1-diacetoxy-1-[2-(acetyloxy)-5-chlorophenyl]methane 在 氯化锆(IV) 作用下， 以 甲醇 为溶剂， 反应 0.13h， 以90%的产率得到(4-氯-2-甲酰基苯基)乙酸酯
  参考文献：
  名称：

  A facile and efficient ZrCl 4 catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage

  摘要：

  A novel, mild and efficient method has been developed for the preparation of geminal-diacetates and dipivalates in high yields through a reaction of aldehydes with acetic anhydride or pivalic anhydride using Zirconium (W) chloride as a catalyst under solvent free conditions. Regeneration of aldehydes from the acylals was also achieved using the same catalyst in CH3OH. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.002

文献信息

• A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3·6H2O as a catalyst under solvent-free conditions
  作者：T. Srikanth Reddy、M. Narasimhulu、N. Suryakiran、K. Chinni Mahesh、K. Ashalatha、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.07.059

  日期：2006.9

  A wide variety of alcohols, phenols and amines are efficiently and selectively converted into the corresponding acetates by treatment with acetic anhydride in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature. The method is compatible with acid sensitive hydroxyl protecting groups such as TBDMS, THP, OBz, OBn, Boc and some isopropylidenes and offers

  在室温下，在无溶剂条件下，在催化量的La（NO 3）3 ·6H 2 O的存在下，通过用乙酸酐处理，可以将各种醇，酚和胺有效，选择性地转化为相应的乙酸酯。该方法与酸敏感的羟基保护基团（例如TBDMS，THP，OBz，OBn，Boc和一些异丙叉）兼容，并提供1,3-，1,4-和1,5-二醇单乙酸酯的优异收率。
• The synthesis and anticancer activity of 2-styrylquinoline derivatives. A p53 independent mechanism of action
  作者：Anna Mrozek-Wilczkiewicz、Michał Kuczak、Katarzyna Malarz、Wioleta Cieślik、Ewelina Spaczyńska、Robert Musiol

  DOI：10.1016/j.ejmech.2019.05.061

  日期：2019.9

  A series of styrylquinolines was designed and synthesized based on the four main quinoline scaffolds including oxine, chloroxine and quinolines substituted with a hydroxyl group or chlorine atom at the C4 position. All of the compounds were tested for their anticancer activity on wild-type colon cancer cells (HCT 116) and those with a p53 deletion. Analysis of SAR revealed the importance of electron-withdrawing

  基于四个主要的喹啉骨架设计并合成了一系列的苯乙烯基喹啉，这些骨架包括在C4位置被羟基或氯原子取代的牛，氯辛和喹啉。测试了所有化合物对野生型结肠癌细胞（HCT 116）和具有p53缺失的癌细胞的抗癌活性。SAR分析表明，在苯乙烯基部分有吸电子取代基，在喹啉环上具有螯合性能。还在TP53突变的4种癌细胞系中测试了活性更高的化合物肿瘤抑制基因。结果表明，苯乙烯基喹啉可诱导细胞周期停滞并激活p53非依赖性细胞凋亡。研究了最有前途的化合物的表观作用机理，这些化合物产生了活性氧，并改变了细胞的氧化还原平衡。
• Synthesis of 1,1-diacetates catalysed by silica-supported boron sulfonic acid under solvent-free conditions and ambient temperature
  作者：Sami Sajjadifar、Sobhan Rezayati

  DOI：10.2478/s11696-013-0480-z

  日期：2014.1.1

  1,1-Diacetates derivatives were prepared using the direct condensation of aldehydes with acetic anhydride in the presence of silica-supported boron sulfonic acid (SiO2/B(SO4H)3) as a tri-functional inorganic Brønsted acid catalyst under solvent-free conditions at ambient temperature. The salient features of this methodology are: (i) cheaper process ready availability of the catalyst; (ii) versatility; (iii) high regio-selectivity of the procedure and recyclable property of the catalyst.

  通过在无溶剂条件下，在室温下使用硅胶负载硼磺酸（SiO2/B(SO4H)3）作为三功能无机布朗斯特酸催化剂，直接将醛类与乙酸酐进行缩合反应，制备了1,1-二醋酸酯衍生物。该方法的显著特点包括：(i) 催化剂价格便宜，易得；(ii) 多功能性；(iii) 过程的高区域选择性和催化剂的可回收性。

• [EN] INHIBITORS OF GLUCOSE TRANSPORTERS (GLUTS)<br/>[FR] INHIBITEURS DE TRANSPORTEURS DE GLUCOSE (GLUT)
  申请人：LEAD DISCOVERY CENTER GMBH

  公开号：WO2020049124A1

  公开（公告）日：2020-03-12

  The present invention relates to 2,6-methanobenzo[g][1]oxacin-4-onecompounds and their analog compounds and pharmaceutically acceptable salts thereof as selective inhibitor of glucose transporters 1 and 3 (GLUTs 1 and 3), to methods of preparing said compounds, and to the use thereof as pharmaceutically active agents, especially for the prophylaxis and/or treatment of metabolic diseases, immunological diseases, autoimmune diseases, inflammation, graft versus host disease, cancer, and metastasis thereof. Furthermore, the present invention is directed to pharmaceutical composition comprising at least one of 2,6-methanobenzo[g][1]oxacin-4-one compounds and their analog compounds.

  本发明涉及2,6-甲烷基苯并[g][1]噁氧嗪-4-酮化合物及其类似物化合物和其药用盐，作为选择性抑制葡萄糖转运蛋白1和3（GLUTs 1和3）的药物，以及制备该类化合物的方法，以及将其用作药用活性剂，特别是用于预防和/或治疗代谢性疾病、免疫性疾病、自身免疫疾病、炎症、移植物抗宿主病、癌症及其转移的方法。此外，本发明还涉及包含至少一种2,6-甲烷基苯并[g][1]噁氧嗪-4-酮化合物及其类似物的药物组合物。
• Synthesis, molecular docking and biological evaluation of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents
  作者：Ru Yan、Zhi-Ming Zhang、Xian-Ying Fang、Yang Hu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.01.023

  日期：2012.2

  A series of novel 1,3,4-oxadiazole derivatives (5a–5s) have been designed, synthesized and evaluated for their immunosuppressive activity. Most of these synthesized compounds were proved to have potent immunosuppressive activity and low toxicity. Among them, compounds (5m–5r) showed the most potent biological activity against lymph node cells. The results of flow cytometry (FCM) and western blotting

  已经设计，合成和评估了一系列新颖的1,3,4-恶二唑衍生物（5a - 5s）的免疫抑制活性。这些合成的化合物大多数被证明具有有效的免疫抑制活性和低毒性。其中，化合物（5m - 5r）显示出对淋巴结细胞最有效的生物学活性。流式细胞术（FCM）和蛋白质印迹的结果表明，化合物5q通过抑制PI3 K / AKT途径诱导细胞凋亡。进行分子对接以将化合物5q定位到PI3Kγ结合位点，以探索潜在的靶标。