3-(4-nitrophenyl)-1H-isochromen-1-one | 22115-46-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(4-nitrophenyl)-1H-isochromen-1-one
• 英文别名: 3-(p-nitrophenyl)isocoumarin；1h-2-Benzopyran-1-one,3-(4-nitrophenyl)-；3-(4-nitrophenyl)isochromen-1-one
• CAS: 22115-46-4
• 化学式: C₁₅H₉NO₄
• 分子量: 267.241
• InChiKey: YTHAAXJVSJVEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻羧基苯乙酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三氯氧磷 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 3-(4-nitrophenyl)-1H-isochromen-1-one
  参考文献：
  名称：

  Palladium catalyzed Suzuki Miyaura cross coupling of 3-chloroisochromen-1-one: synthesis of glomellin and reticulol analogues

  摘要：

  A facile protocol has been developed for a series of 3-substituted isochromen-1-ones utilizing Suzuki coupling strategy. The reaction of 3-chloroisochromen-1 one, 1 with different boronic acids utilizing PdCl2(PPh3)(2)-Ruphos catalytic system gave diversified 3-substituted isochromen-1-ones in excellent yields. The methodology has been utilized in the synthesis of glomellin and reticulol analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.114

文献信息

• 3-Substituted Isocoumarins as Thymidine Phosphorylase Inhibitors
  作者：Khalid Mohammed Khan、Sumbul Ahmed、Sajjad Hussain、Nida Ambreen/snm、>、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.2174/157018010790945805

  日期：2010.5.1

  3-Substituted isocoumarins 1-19 were synthesized and evaluated for their thymidine phosphorylase inhibitory activity. Eight (8) compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase from E. coli with IC50 values between 61- 402 iM. The activities were compared with the standard 7-deazaxanthine (IC50 = 39.28 ± 0.76 iM).

  合成了3-取代异香豆素1-19，并评估了它们对大肠杆菌胸苷磷酸化酶的抑制活性。其中8个化合物表现出不同程度的抑制作用，IC50值介于61至402微摩尔之间。将这些活性与标准物质7-去氮黄嘌呤（IC50 = 39.28 ± 0.76微摩尔）进行比较。
• Silver triflate/<i>p</i>-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates
  作者：Jonathan Gianni、Valentina Pirovano、Giorgio Abbiati

  DOI：10.1039/c8ob00436f

  日期：——

  In this paper, we describe the silver triflate/p-toluenesulfonic acid co-catalysed synthesis of seventeen isocoumarins and two thieno[2,3-c]pyran-7-ones starting from 2-alkynylbenzoates and 3-alkynylthiophene-2-carboxylates, respectively. The reaction proceeds with absolute regioselectivity under mild reaction conditions and low catalyst loading, to afford the desired products in good to excellent

  在本文中，我们描述了三氟甲磺酸银/对甲苯磺酸共催化合成17个异香豆素和两个由2-炔基苯甲酸酯和3-炔基噻吩-2-羧酸酯组成的噻吩并[2,3 - c ]吡喃-7-，分别。反应在温和的反应条件下和低的催化剂载量下以绝对的区域选择性进行，以良好至极好的收率提供所需的产物。提出了一种可能的反应机理，并得到了同位素交换试验，1 H NMR研究和特别实验的支持。
• Ru(<scp>ii</scp>)-Catalyzed C–H bond activation/annulation of <i>N</i>-iminopyridinium ylides with sulfoxonium ylides
  作者：Xiang Li、Danlu Li、Xiaofei Zhang

  DOI：10.1039/d1ob02427b

  日期：——

  A Ru(II)-catalyzed C–H bond activation/annulation of N-iminopyridinium ylides with sulfoxonium ylides has been developed for the synthesis of diverse functionalized isocoumarin derivatives. This method features broad substrate scope, high functional group tolerance, simple operation and silver salt-free conditions. Furthermore, the synthetic utility of this method is demonstrated by the alkenylation

  已经开发了一种 Ru( II ) 催化的N-亚氨基吡啶叶立德与锍叶立德的 C-H 键活化/环化，用于合成各种官能化的异香豆素衍生物。该方法具有底物范围广、官能团耐受性高、操作简单、无银盐条件等特点。此外，该方法的合成效用通过产物的烯基化和生物活性 thunberginol A 的有效合成得到证明。
• Correction to Synthesis of 3-Substituted Isocoumarins via Cascade Intramolecular Ullmann-Type Coupling–Rearrangement Process
  作者：Zhi-Yuan Ge、Xiang-Dong Fei、Ting Tang、Yong-Ming Zhu、Jing-Kang Shen

  DOI：10.1021/jo3021117

  日期：2012.10.19

  Page 5738. Entries 12–19 of Table 2 were inadvertently omitted. The corrected version of Table 2 follows: The reactions were performed in a sealed tube with 1 (0.5 mmol), CuI (0.05 mmol), 2-picolinic acid (0.1 mmol), and K2CO3 (1.0 mmol) in toluene (2 mL) at 110 °C under nitrogen. Isolated yield. This article has not yet been cited by other publications.

  页面5738。表2的条目12-19被无意中省略了。表2的修正版本如下：反应在密闭的试管中在甲苯（1（0.5 mmol），CuI（0.05 mmol），2-吡啶甲酸（0.1 mmol）和K 2 CO 3（1.0 mmol）中进行。 2毫升）在110°C下在氮气下。孤立的产量。本文尚未被其他出版物引用。
• Synthesis of 3-Substituted Isocoumarins via a Cascade Intramolecular Ullmann-Type Coupling–Rearrangement Process
  作者：Zhi-Yuan Ge、Xiang-Dong Fei、Ting Tang、Yong-Ming Zhu、Jing-Kang Shen

  DOI：10.1021/jo300916s

  日期：2012.7.6

  highly efficient strategy for the synthesis of 3-substituted isocoumarins through a copper(I)-catalyzed reaction of 1-(2-halophenyl)-1,3-diones has been developed. The procedure is based on a cascade copper-catalyzed intramolecular Ullmann-type C-arylation and rearrangement process. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.

  通过铜（I）催化的1-（2-卤代苯基）-1,3-二酮的反应合成3-取代的香豆素的简单高效的策略已被开发出来。该程序基于级联铜催化的分子内Ullmann型C-芳基化和重排过程。这种方法可以耐受多种底物，并适用于文库合成。