9-hydroxy-1-methyl-3H-naphtho[2,1-b]pyran-3-one | 51142-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 9-hydroxy-1-methyl-3H-naphtho[2,1-b]pyran-3-one
• 英文别名: 9-hydroxy-1-methylbenzo[f]chromen-3-one
• CAS: 51142-93-9
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: XRTVSACRRXWWAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  128-170 °C
• 沸点：
  472.1±30.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-hydroxy-1-methyl-3H-naphtho[2,1-b]pyran-3-one 在 PPA 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 3H-1,8,9-trimethylfuro[3',2':6,7]naphtho[2,1-b]pyran-3-one
  参考文献：
  名称：

  Regioselective synthesis and photooxygenations of furonaphthopyrones starting from 2,7-naphthalenediol

  摘要：

  Three angular furonaphthopyrones 4, 9, 12 were regioselectively synthesized starting from 2,7-naphthalenediol in three steps, respectively. An easy separation of Pechmann condensation products 1 and 2 of 2,7-naphthalenediol with ethyl acetoacetate was described. The photooxygenations of 4, 12 were investigated and a hydroperoxide 18 was isolated and fully characterized. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00845-4
• 作为产物：
  描述：

  2,7-二羟基萘 在 硫酸 、 苯 作用下， 生成 9-hydroxy-1-methyl-3H-naphtho[2,1-b]pyran-3-one
  参考文献：
  名称：

  Perekalin; Padwa, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2578,2582, 2583; engl. Ausg. S. 2635, 2638,2639

  摘要：

  DOI：

文献信息

• Phenacyl ester derivatives bearing heterocycles as models for photocleavable linkers: synthesis and photolysis studies
  作者：Andrea S.C. Fonseca、M. Sameiro T. Gonçalves、Susana P.G. Costa

  DOI：10.1016/j.tet.2012.06.100

  日期：2012.9

  The synthesis of several phenacyl ester derivatives linked to oxygen and nitrogen heterocycles, benzoquinolone and (benzo)coumarins, was carried out in an effort to obtain systems that could be applied as photocleavable (bi)functional linkers for solid phase peptide synthesis. The heterocycles were attached to a spacer, with different lengths, followed by coupling to 2-bromo-1-phenylpropan-1-one, acting

  进行了一些与氧和氮杂环，苯并喹诺酮和（苯并）香豆素连接的苯甲酸酯衍生物的合成，以期获得可用作固相肽合成的光可裂解（双功能）接头的体系。将杂环连接至具有不同长度的间隔基，然后偶联至充当固体支持物模型的2-溴-1-苯基丙烷-1-酮。在甲醇/ HEPES缓冲溶液（80:20）中，通过在光化学反应器中以不同波长（300、350和419 nm）进行辐照，对所得的苯甲酸酯衍生物进行光解研究。
• Synthesis and structure of indoline spiropyrans based on benzo[f]coumarin
  作者：O. G. Nikolaeva、O. Yu. Karlutova、A. A. Guseva、E. B. Gaeva、A. G. Starikov、A. D. Dubonosov、V. A. Bren、A. V. Metelitsa、V. I. Minkin

  DOI：10.1007/s11172-020-2912-6

  日期：2020.7

  Indoline spiropyrans containing benzo[f]coumarin moiety annulated to the 2H-pyran cycle were synthesized. The obtained compounds exist in solutions as a tautomeric mixture of their spirocyclic and merocyanine forms. The spiro form exhibits an enhanced resistance to UV irradiation and does not rearranges into the merocyanine isomer in the temperature range of 278–303 K.

  合成了含有与 2H-吡喃循环成环的苯并[f]香豆素部分的二氢吲哚螺吡喃。所得化合物以其螺环和部花青形式的互变异构混合物存在于溶液中。螺形式对紫外线照射具有增强的抵抗力，并且在 278-303 K 的温度范围内不会重新排列成部花青异构体。
• Synthesis and Luminescence and Ionochromic Properties of 9-Hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene8-carbaldehyde Imines and Hydrazones
  作者：O. G. Nikolaeva、O. Yu. Karlutova、A. D. Dubonosov、V. A. Bren、V. I. Minkin

  DOI：10.1134/s107036322002005x

  日期：2020.2

  enzo[f]chromene-8-carbaldehyde which was converted to the corresponding aldehyde imines and aroylhydrazones. According to the 1H NMR and UV spectral data, 9-hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde imines in solution exist as ketone tautomers, whereas its aroylhydrazones have enol structure. 9-Hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde aroylhydrazones are multifunctional

  摘要9-羟基-1-甲基-3 H-苯并[ f ]铬烯-3-酮与六亚甲基四胺在乙酸中的甲酰化反应，得到9-羟基-1-甲基-3-氧代-3 H-苯并[ f ]烯酮-8 -甲醛，将其转化为相应的醛亚胺和芳酰基hydr。根据1 H NMR和UV光谱数据，溶液中的9-羟基-1-甲基-3-氧代-3 H-苯并[ f ]色烯-8-甲醛亚胺以酮互变异构体的形式存在，而其芳酰基hydr具有烯醇结构。9-羟基-1-甲基-3-氧代-3 H-苯并[ f ]色烯-8-甲醛芳酰基hydr是多功能的离子变色化合物，能够与d金属阳离子，以及氟化物，氰化物和乙酸根阴离子。络合导致起始化合物的吸收和荧光性质的转换。金属阳离子导致肉眼可见的溶液颜色从无色变为亮橙色，并发生荧光猝灭，而在存在阴离子的情况下，颜色变为红色并伴有红移并增加了发射强度。
• Synthesis and Characterization of New Helical Coumarins
  作者：Harish R. Talele、Firasat Hussain、Ashutosh V. Bedekar

  DOI：10.1002/jhet.2193

  日期：2015.5

  phenomenon of peri interaction of 1,8‐disubstituted naphthalene has been utilized to construct small molecules with internal twist resulting in helical isomers. A series of new naphthalene‐attached coumarins have been synthesized and characterized. The helical conformational twist in thiophene–coumarin capped naphthalene was established by H‐NMR and single crystal X‐ray diffraction analysis.

  1,8-二取代萘的周边相互作用现象已被用于构建内部扭曲的小分子，从而形成螺旋异构体。已合成并表征了一系列新型的萘基香豆素。通过H-NMR和单晶X射线衍射分析确定了噻吩-香豆素封端的萘中的螺旋构象扭曲。
• Highly Efficient Photoinduced DNA Cleavage by Naphthopyrone Hydroperoxides
  作者：Zhi-Fu Tao、Xuhong Qian、Mingcai Fan

  DOI：10.1246/bcsj.72.1571

  日期：1999.7

  naphthopyrone hydroperoxides as novel photochemical DNA cleavers were synthesized and evaluated. Their photochemical DNA-cleaving abilities depend on skeleton arrangement of the naphthopyrone core and are much more efficient than those of the reported 1,8-naphthalenedicarboximide analog. The DNA-cleaving mechanism by these new hydroperoxides probably mainly involves hydroxyl radicals, indicating that

  合成并评估了各种作为新型光化学 DNA 切割剂的萘并吡喃氢过氧化物。它们的光化学 DNA 切割能力取决于萘并吡喃酮核心的骨架排列，并且比报道的 1,8-萘二甲酰亚胺类似物的效率高得多。这些新型氢过氧化物的 DNA 切割机制可能主要涉及羟基自由基，表明萘并吡喃氢过氧化物可能能够作为一类新的嵌入光芬顿试剂。