4,9-dihydroxy-5-oxo-1,2,4,5-tetrahydro-4,11a-methanooxocino[4,5-b]benzofuran-2-carboxylic acid | 1170720-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4,9-dihydroxy-5-oxo-1,2,4,5-tetrahydro-4,11a-methanooxocino[4,5-b]benzofuran-2-carboxylic acid
• 英文别名: 5,12-Dihydroxy-11-oxo-2,13-dioxatetracyclo[10.3.1.01,9.03,8]hexadeca-3(8),4,6,9-tetraene-14-carboxylic acid；5,12-dihydroxy-11-oxo-2,13-dioxatetracyclo[10.3.1.01,9.03,8]hexadeca-3(8),4,6,9-tetraene-14-carboxylic acid
• CAS: 1170720-51-0
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: AGTNMBXKAJGXKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,9-dihydroxy-5-oxo-1,2,4,5-tetrahydro-4,11a-methanooxocino[4,5-b]benzofuran-2-carboxylic acid 、 三氟甲烷磺酸甲酯 以 二甲基亚砜 为溶剂， 反应 20.0h， 以26%的产率得到
  参考文献：
  名称：

  Structure and Formation of the Fluorescent Compound of Lignum nephriticum

  摘要：

  The intense blue fluorescence of the infusion of Lignum nephriticum (Eysenhardtia polystachya), first observed in the sixteenth century, is due to a novel four-ring tetrahydromethanobenzofuro[2,3-d]oxacine which is not present in the plant but is the end product of an unusual, very efficient iterative spontaneous oxidation of at least one of the tree's flavonoids.

  DOI：

  10.1021/ol901022g
• 作为产物：
  描述：

  α3,4,2',4'-pentahydroxydihydrochalcone 在 sodium hydroxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以75%的产率得到4,9-dihydroxy-5-oxo-1,2,4,5-tetrahydro-4,11a-methanooxocino[4,5-b]benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Structure and Formation of the Fluorescent Compound of Lignum nephriticum

  摘要：

  The intense blue fluorescence of the infusion of Lignum nephriticum (Eysenhardtia polystachya), first observed in the sixteenth century, is due to a novel four-ring tetrahydromethanobenzofuro[2,3-d]oxacine which is not present in the plant but is the end product of an unusual, very efficient iterative spontaneous oxidation of at least one of the tree's flavonoids.

  DOI：

  10.1021/ol901022g

文献信息

• Synthesis and photophysics of novel biocompatible fluorescent oxocines and azocines in aqueous solution
  作者：A. Ulises Acuña、Mónica Álvarez-Pérez、Marta Liras、Pedro B. Coto、Francisco Amat-Guerri

  DOI：10.1039/c3cp52228h

  日期：——

  accompanying monardine ionization which may abolish de-excitation via intersystem crossing. A similar fluorogenic reaction takes place with catecholamines such as dopamine and DOPA, to yield fluorescent azocines 2a and 2b which, depending on pH, may be present as cationic, neutral or anionic species. TDDFT computations of these forms were also carried out to assign the corresponding excitation transitions

  不同质子形式的强荧光半缩醛4,9-二羟基-1,2-二氢-4,11a-甲氧羰基[4,5 - b ]苯并呋喃-5（4 H）-（1a，莫纳ardine），氮杂类似物4，9-二羟基-3，4-二氢-1 H -4，11a-甲基苯并呋喃[2，3 - d ]偶氮素-5（2 H）-1（2a，氮莫尼丁）和各自的2-羧基衍生物（1b，2b）已通过实验和量子化学方法进行了研究。莫纳丁和羧莫纳丁分别是水溶液中羟基酪醇或丹酚酸的新型荧光室温反应的主要产物，它们具有独特的光物理性质。接近中性pH（p K a = 7.2）的黄嘌呤从弱发射，吸收紫外线的（382 nm）中性物质切换为吸收VIS（426 nm），发射蓝光（464 nm）的阴离子形式，并具有荧光量子产率φ ˚F = 1和单指数衰减τ ˚F= 2.74 ns。基于时间相关的密度泛函理论（TDDFT）计算，解释了这种从中性到阴离子形式的二元光谱变化，这是由于（i）
• Structure and Formation of the Fluorescent Compound of <i>Lignum nephriticum</i>
  作者：A. Ulises Acuña、Francisco Amat-Guerri、Purificación Morcillo、Marta Liras、Benjamín Rodríguez

  DOI：10.1021/ol901022g

  日期：2009.7.16

  The intense blue fluorescence of the infusion of Lignum nephriticum (Eysenhardtia polystachya), first observed in the sixteenth century, is due to a novel four-ring tetrahydromethanobenzofuro[2,3-d]oxacine which is not present in the plant but is the end product of an unusual, very efficient iterative spontaneous oxidation of at least one of the tree's flavonoids.