9-(2-hydroxynaphthalen-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one | 1441019-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(2-hydroxynaphthalen-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 9-(2-Hydroxynaphthalen-1-yl)-2,3,4,9-tetrahydroxanthen-1-one；9-(2-hydroxynaphthalen-1-yl)-2,3,4,9-tetrahydroxanthen-1-one
• CAS: 1441019-39-1
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: DBRLIKXZWQOHNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 水杨醛 、 2-萘酚 在 graphite oxide 作用下， 以 水 为溶剂， 反应 3.0h， 以87%的产率得到9-(2-hydroxynaphthalen-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  使用可重复使用的氧化石墨碳催化剂在水性和无溶剂反应条件下高效无金属绿色合成 4H-色烯和 3-氨基烷基化吲哚

  摘要：

  氧化石墨 (GO) 分别用于在水和无溶剂反应条件下一锅三组分合成药学上重要的 4 H-色烯和 3-氨基烷基化吲哚。FT-IR、XPS、SEM、TEM、SAED、EDX、PXRD、拉曼和 TGA 等光谱技术证实了 GO 的形成和热稳定性。这些协议提供了绿色和可持续的反应条件，包括优异的催化活性、良好的产品产率、催化剂的可重复使用性、高官能团耐受性和克级合成。此外，本方法排除了金属毒性、金属废物处理、产品中的金属污染以及挥发性有机溶剂的使用等问题。

  DOI：

  10.1039/d2nj00756h

文献信息

• An efficient solvent free Amberlite IRA-400 Cl resin mediated multicomponent synthesis and photophysical properties of fluorescent 4 H -chromene derivatives
  作者：Gurusamy Harichandran、Parkunan Parameswari、Ponnusamy Shanmugam

  DOI：10.1016/j.dyepig.2016.12.026

  日期：2017.4

  An efficient Amberlite IRA-400 Cl basic anion exchange resin mediated multicomponent reaction of 2-hydroxybenzaldehydes, 1, 3-diketone and nucleophiles under neat condition afforded a number of fluorescent 4H-chromene derivatives in excellent yield. The structure of the synthesized compounds 4k and 4u were confirmed from single crystal XRD studies. 4H-Among the chromene derivatives, compound 4v synthesized

  在纯净条件下，高效的Amberlite IRA-400 Cl碱性阴离子交换树脂介导的2-羟基苯甲醛，1、3-二酮和亲核试剂的多组分反应以优异的收率提供了许多荧光4 H-色烯衍生物。通过单晶XRD研究证实了合成的化合物4k和4u的结构。4 H-色烯衍生物中的化合物4v由4-二乙氨基取代的2-羟基苯甲醛与二甲酮和2-羟基萘醌合成的最佳荧光材料。已经评估了所选化合物的光物理性质，如溶剂变色效应，吸收，发射，库仑位移和量子产率。合成化合物的发射特性表明它们是一类蓝色发光荧光材料。
• Nanocrystalline and Reusable ZnO Catalyst for the Assembly of Densely Functionalized 4<i>H</i>-Chromenes in Aqueous Medium via One-Pot Three Component Reactions: A Greener “NOSE” Approach
  作者：Partha Pratim Ghosh、Asish R. Das

  DOI：10.1021/jo400763z

  日期：2013.6.21

  An ecofriendly, One-pot, three component ZnO nanoparticles-mediated synthesis of 4H-chromene in water under thermal condition has been described. The highly product-selective three component electrophilic reaction of 2-hydroxybenzaldehyde with an active methylene compound and another carbon-based varied nature of nucleophile has been developed by a reversible alkylation procedure using greener "NOSE" approach. Greenness of the process was well instituted, as water was used both;as reaction media as well as medium for the synthesis of catalyst. In these reactions, the use of nano-ZnO as a catalyst was documented to be crucial for rendering the reactions possible in water media, while replacing nano-ZnO with other acids or bases resulted in the generation of too many side products. The catalyst can be efficiently recycled up to the sixth run, an essential point in the area of green chemistry. The methodology provides cleaner conversion, shorter reaction times, and high selectivity, which make the protocol globally putative. The crystal structures of 4H-chromene, easily produced by a chromatography-free highly product-selective reaction, were explored by means of single crystal X-ray diffraction analysis, and H-bonding arrangements of one signified compound prepared is presented. In optimized mild conditions, the isolated yields are 86-93%.