3-氧代-3H-萘并[1,2-b]吡喃-1-乙酸 | 33739-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: 3-氧代-3H-萘并[1,2-b]吡喃-1-乙酸
• 英文名称: 3(H)-oxonaphtho<2,1-b>pyran-1-acetic acid
• 英文别名: 3-oxo-3H-naphtho<1,2-b>pyran-1-acetic acid；2-(3-oxo-3H-benzo[f]chromen-1-yl)acetic acid；5,6-benzocoumarin-4-acetic acid；(3-oxo-3H-benzo[f]chromen-1-yl)-acetic acid；(3-Oxo-3H-benzo[f]chromen-1-yl)-essigsaeure；(3-oxo-3H-benzo[f]chromen-1-yl)acetic acid；2-(3-oxobenzo[f]chromen-1-yl)acetic acid
• CAS: 33739-01-4
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: IAOKPZIEZYJMKM-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  531.7±38.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氧代-3H-萘并[1,2-b]吡喃-1-乙酸 在 1-羟基苯并三唑 、 copper(II) sulfate 、 sodium ascorbate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 14.0h， 生成 5'-deoxy-5'-{4-[2-(3-oxo-3H-benzochromen-7-yl)acetamidomethyl]-1H-1,2,3-triazol-1-yl}uridine
  参考文献：
  名称：

  通过Huisgen 1,3-偶极环加成反应合成香豆素-核苷共轭物

  摘要：

  描述了一种通过Cu（I）催化的Huisgen 1,3-偶极环加成反应合成荧光香豆素-核苷共轭物的有效方法。从叠氮核苷和香豆素衍生物开始，以高收率获得产物。确定了新制备的香豆素-核苷结合物的荧光性质。

  DOI：

  10.1016/j.tet.2006.10.075
• 作为产物：
  描述：

  3-氧丁酸 、 2-萘酚 在 硫酸 作用下， 以76%的产率得到3-氧代-3H-萘并[1,2-b]吡喃-1-乙酸
  参考文献：
  名称：

  Mashelkar; Tungare, Shefali S.; Bhagat, Sachin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 3, p. 315 - 320

  摘要：

  DOI：

文献信息

• Synthesis of Novel Coumarin-Based Fluorescent Probes
  作者：Ivana Kosiova、Pavol Kois

  DOI：10.1135/cccc20070996

  日期：——

  We report on synthesis of new fluorescent probes suitable for site-specific incorporation into oligonucleotides. Coumarin derivatives were used as sensitive fluorescent labels and were attached to glycerol unit by two types of linkers as potential building blocks for oligonucleotide synthesis. Spectral characteristics of the functionalized coumarin building blocks were measured.

  我们报告了合成适用于特定位置嵌入寡核苷酸的新荧光探针。香豆素衍生物被用作敏感的荧光标记，并通过两种类型的连接剂连接到甘油单元，作为寡核苷酸合成的潜在构建块。测量了功能化香豆素构建块的光谱特性。
• Synthesis of novel coumarin and benzocoumarin derivatives and their biological and photophysical studies
  作者：Alaa S. Abd-El-Aziz、Hany M. Mohamed、Shawkat Mohammed、Shamsulhaq Zahid、Athar Ata、Ahmed H. Bedair、Ahmed M. El-Agrody、Pierre D. Harvey

  DOI：10.1002/jhet.5570440610

  日期：2007.11

  The reaction of 1-chloromethylbenzo[f]coumarins (36) with cyanide anion under different reaction conditions was also investigated in order to assess its suitability for nucleophilic substitution reactions as well as ring transformation products (43-49). Synthesis of 1-((benzo[d]thiazol-2-yl)methyl)-9-hydroxybenzo[f]coumarin (50) represented the first example of methylene bridge-head heterocyclecontaining

  通过香豆素-3-羰基氯（1）与许多亲核试剂的反应已经制备了香豆素-3 N-羧酰胺的几种衍生物（3-21）。还使用相同的方法制备了新型双头香豆素-3 N-羧酰胺（26-33）。应用Pechmann-Duisberg反应制备新的苯并[ f ]-苯并[ h ]香豆素和4-（氯甲基）-吡喃并[3,2 - c ]香豆素-2-酮（36-42）。1-氯甲基苯并[ f ]香豆素的反应（36）还研究了在不同反应条件下与氰化物阴离子形成的阴离子，以评估其对亲核取代反应以及环转化产物的适用性（43-49）。1-（（苯并[ d ]噻唑-2-基）甲基）-9-羟基苯并[ f ]香豆素（50）的合成代表了含亚甲基桥头杂环的苯并[ f ]香豆素的第一个实例。一些新制备的香豆素对革兰氏阳性和革兰氏阴性细菌表现出抗菌活性。发现化合物36d对所有经筛选的细菌具有活性。对选定的荧光苯并[ f ]-和苯并[ h ]进行了光物理研究
• Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones
  作者：Abram N. Brubaker、Jack De Ruiter、William L. Whitmer

  DOI：10.1021/jm00156a031

  日期：1986.6

  A number of 4,7-disubstituted benzopyran-2-ones were synthesized and evaluated for crude rat lens aldose reductase inhibitory activity. Substituents on position 4 included CH3, CO2H, CH2CO2H, CH = CHCO2H, and CH2CH2CO2H. The aromatic substituents included OH, OCH3, OCOCH3, CH2CH3, and Cl. Also included in the study were 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic, 2-oxo-2H-naphtho[1,2-b]pyran-4-acetic, and 1-naphthylacetic acids. The benzopyran and naphthopyran derivatives were prepared by the classical von Pechmann reaction. General structure-activity relationships reveal that optimal enzyme inhibitory activity is displayed by those compounds possessing the acetic acid moiety. For example, the most potent derivative, 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic acid with an IC50 of 0.020 microM, is as potent as sorbinil (IC50 = 0.017 microM) in the crude rat lens aldose reductase assay.
• Synthetic and Structural Studies on Novel 4,3′-Bicoumarins
  作者：Kiran K. Pujar、Manohar V. Kulkarni、Ganesh N. Alawandi、G. N. Anilkumar、Mahantesha Basanagouda

  DOI：10.1080/00397911.2015.1063656

  日期：2015.9.2

  A series of directly linked 4-3 bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidine using ethanol as solvent and by the reaction of coumarin-4-acetic acids with substituted salicylaldehydes in the presence of sodium hydride in acetic anhydride. Greater yields have been obtained in the sodium hydride and acetic anhydride condition. An intermediate chalcone with an ortho-hydroxyl group, which is a precursor for lactone formation, has been isolated and its structure has been confirmed by x-ray analysis. The nonplanar S-cis arrangement of two C4-C3' double bonds has been confirmed by nuclear Overhauser spectroscopy (NOE) and x-ray studies. The UV-fluorescence studies support the formation of a conjugated bicoumarin system.
• Synthesis and in vitro anti-HIV activity of N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H-chromen-4-yl)acetamide derivatives using MTT method
  作者：Dhairya Bhavsar、Jalpa Trivedi、Shrey Parekh、Mahesh Savant、Shailesh Thakrar、Abhay Bavishi、Ashish Radadiya、Hardevsinh Vala、Jignesh Lunagariya、Manisha Parmar、Ladwa Paresh、Roberta Loddo、Anamik Shah

  DOI：10.1016/j.bmcl.2011.03.105

  日期：2011.6

  A series of novel N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H-chromen-4-yl)acetamide derivatives has been synthesized. All the newly synthesized compounds were evaluated for their anti-HIV activity using MTT method. Most of these compounds showed moderate to potent activity against wild-type HIV-1 with an EC50 ranging from >7 EC50 [mu g/ml] to <100 EC50 [mu g/ml]. Among them, N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H-chromen-4-yl)acetamide 6v was identified as the most promising compound (EC50 = <7 mu g/ml). Among all the compounds, three compounds 6m, 6v and 6u have been exhibits potent anti-HIV activity against MT-4 cells. (C) 2011 Elsevier Ltd. All rights reserved.