4-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2-thioxo-5-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2-thioxo-5-one
• 英文别名: 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydro-5H-chromeno[4,3-d]pyrimidin-5-one；4-(4-chlorophenyl)-2-sulfanylidene-3,4-dihydro-1H-chromeno[4,3-d]pyrimidin-5-one
• 化学式: C₁₇H₁₁ClN₂O₂S
• 分子量: 342.806
• InChiKey: GCHPXVUEVKGLFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 calcium aluminate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2-thioxo-5-one
  参考文献：
  名称：

  One Pot Synthesis of Benzopyranones and Benzoxazinones Catalyzed by MMO

  摘要：

  DOI：

  10.56042/ijc.v61i11.65837

文献信息

• Heteropolyacid@creatin-halloysite clay: an environmentally friendly, reusable and heterogeneous catalyst for the synthesis of benzopyranopyrimidines
  作者：Samahe Sadjadi、Majid M. Heravi、Masoumeh Malmir

  DOI：10.1007/s11164-017-3016-2

  日期：2017.11

  A novel hybrid catalyst has been designed and synthesized based on the incorporation of heteropolyacid into creatin-functionalized halloysite clay. The catalyst was characterized by using SEM/EDS, FTIR, XRD, BET, ICP-AES, TGA and DTGA, and successfully applied for promoting the synthesis of two series of benzopyranopyrimidines under ultrasonic irradiation in aqueous media. The results established the efficiency of this protocol in terms of product yield, reaction time and the eco-friendly nature of the process. Moreover, immobilization of heteropolyacid on creatin-functionalized halloysite circumvents heteropolyacid leaching and rendered the catalyst highly reusable.

  一种新型复合催化剂已被设计和合成，该催化剂是基于将杂多酸引入功能化的肌酸膨润土泥土中。通过使用扫描电子显微镜/能谱仪（SEM/EDS）、傅里叶变换红外光谱（FTIR）、X射线衍射（XRD）、比表面积测定（BET）、电感耦合等离子体原子发射光谱（ICP-AES）、热重分析（TGA）和微分热分析（DTGA）对催化剂进行了表征，并成功应用于促进在水相介质中超声照射下合成两系列苯并吡喃嘧啶。结果证明该方法在产物产率、反应时间和环保性方面的高效性。此外，杂多酸在功能化的肌酸膨润土上的固定化避免了杂多酸的浸出，使得催化剂具有较高的重复使用性。
• Small Molecule Inhibitors of White Spot Syndrome Virus: Promise in Shrimp Seedling Culture
  作者：Lei Liu、Li-Peng Shan、Yan Zhou、Jiong Chen

  DOI：10.3390/ijms22073450

  日期：——

  Rapid production of prawn (Litopenaeus vannamei) under artificial pressure can result in a series of obvious challenges and is vulnerable to serious losses related to aquatic environmental issues and the unrestrained outbreak of white spot syndrome (WSS). However, to date, there are no therapeutic strategies to contain the spread of the virus. Here, we synthesized 27 coumarin derivatives and evaluated their anti-white spot syndrome virus (WSSV) activity in L. vannamei larvae. We demonstrated that electron-withdrawing and electron-giving substituent groups play an important role in reducing toxicity and WSSV replication, respectively. Two coumarin C2 (2-amino-5-oxo-4-(p-tolyl)-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile) and C7 (2-amino-4-(4-chlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile) were regarded as the most promising anti-WSSV compounds with maximum antiviral response <5% and median effective concentration <10 mg/L. The mortality of WSSV-infected larvae decreased by more than 60% after exposure to C2 and C7. With continuous immersion of C2 and C7 exchange, the mortality further decreased to 40% at 120 h. Additionally, C2 and C7 are the relatively stable in aquacultural water, making these agents suitable for use in inhibiting WSSV horizontal transmission in static aquaculture systems. These results showed the marked advantages of using C2 and C7 in the shrimp industry, and suggest that they hold potential for the treatment and prevention of WSSV infection in shrimp seedling culture.

  通过人工压力快速生产对虾（Litopenaeus vannamei）可能导致一系列明显挑战，并容易受到与水生环境问题和白斑综合征（WSS）的不受限制爆发有关的严重损失。然而，迄今为止，尚无治疗策略来控制病毒传播。在这项研究中，我们合成了27种香豆素衍生物，并评估它们对L. vannamei幼虾的抗白斑综合征病毒（WSSV）活性。我们证明了电子吸引和电子给予取代基在减少毒性和WSSV复制方面发挥着重要作用。两种香豆素C2（2-氨基-5-氧代-4-(对甲苯基)-4H,5H-吡喃[3,2-c]咔喃-3-碳腈）和C7（2-氨基-4-(4-氯苯基)-5-氧代-4H,5H-吡喃[3,2-c]咔喃-3-碳腈）被认为是最有前景的抗WSSV化合物，最大抗病毒反应＜5％，半数有效浓度＜10毫克/升。暴露于C2和C7后，WSSV感染的幼虾死亡率下降了60％以上。随着C2和C7交换的持续浸泡，死亡率在120小时内进一步降至40％。此外，C2和C7在水产养殖水中相对稳定，使这些药物适用于在静态水产养殖系统中抑制WSSV的水平传播。这些结果显示了在虾业中使用C2和C7的显著优势，并表明它们具有潜力用于虾苗培育中WSSV感染的治疗和预防。
• One-pot facile and mild construction of densely functionalized pyrimidines in water <i>via</i> consecutive C–C and C–S bonds formation
  作者：Pramod K. Sahu、Praveen K. Sahu、Manvendra S. Kaurav、Mouslim Messali、Saud M. Almutairi、Puran L. Sahu、Dau D. Agarwal

  DOI：10.1039/c8ra04363a

  日期：——

  Fused pyrimidines composed of alternating heteroatoms and a pyrimidine moiety were synthesized efficiently using readily available starting material 4-hydroxycoumarin, aromatic aldehydes, and urea/thiourea at room temperature.

  利用现成的起始材料 4-羟基香豆素、芳香醛和脲/硫脲，在室温下高效合成了由交替杂原子和嘧啶分子组成的融合嘧啶。
• Bio-assisted synthesized Ag(0) nanoparticles immobilized on SBA-15/cyclodextrin nanosponge adduct: Efficient heterogeneous catalyst for the ultrasonic-assisted synthesis of benzopyranopyrimidines
  作者：Samahe Sadjadi、Majid M. Heravi、Masoumeh Malmir

  DOI：10.1002/aoc.4286

  日期：2018.4

  SBA‐15/cyclodextrin nanosponge adduct was synthesized through reaction of Cl‐functionalized SBA‐15 and amine‐functionalized cyclodextrin nanosponge (CDNS). This adduct, which benefits from features of both SBA‐15 and CDNS, was then used for immobilization of Ag(0) nanoparticles which were prepared and capped using a bio‐based approach. Ag@CDNS–SBA‐15 was applied as a heterogeneous catalyst for promoting

  首次通过Cl官能化的SBA-15与胺官能化的环糊精纳米海绵（CDNS）的反应合成了SBA-15 /环糊精纳米海绵加合物。该加合物得益于SBA-15和CDNS的功能，然后被用于固定Ag（0）纳米颗粒，这些纳米颗粒是使用生物基方法制备和封端的。Ag @ CDNS–SBA-15被用作非均相催化剂，用于在超声辐射下促进苯甲醛，4-羟基香豆素和尿素或硫脲的三组分反应，以提供苯并吡喃并嘧啶。反应变量使用响应面方法进行了优化。Ag @ CDNS–SBA-15的催化活性高于Ag @ CDNS，Ag @ SBA-15和Ag @ SBA-15 + CDNS，确认这两种成分对催化的贡献以及CDNS和SBA-15之间的协同作用。CDNS的作用是容纳基质并将其带到Ag（0）纳米颗粒附近。值得注意的是，该催化剂是可重复使用的，并且可以回收利用，最多可重复使用四个反应，轻微的Ag（0）浸出并失去催化活性。
• Reaction of Coumarin Derivatives with Nucleophiles in Aqueous Medium
  作者：Mazaahir Kidwai、Priya、Shweta Rastogi

  DOI：10.1515/znb-2008-0110

  日期：2008.1.1

  A series of heterocycles was synthesized by the reaction of α,β -unsaturated ketones of benzopyrans or coumarins with various nucleophiles in aqueous medium bearing two points of diversity. Compared to an identical library generated by conventional parallel synthesis, a microwaveassisted procedure dramatically decreased reaction times from hours to minutes, and yields of products and intermediates

  通过苯并吡喃或香豆素的α,β-不饱和酮与各种亲核试剂在具有两点多样性的水性介质中反应合成了一系列杂环。与通过常规平行合成生成的相同库相比，微波辅助程序将反应时间从数小时显着缩短到数分钟，并且产物和中间体的产率显着提高。这种合成方法本质上是环保的，其特点是水作为溶剂、微波辐射和“绿色”催化剂（K2CO3）的使用。