benzyl 9,10-dimethoxyanthracene-2-sulphonate | 131290-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: benzyl 9,10-dimethoxyanthracene-2-sulphonate
• 英文别名: benzyl 9,10-dimethoxyanthracene-2-sulfonate
• CAS: 131290-09-0
• 化学式: C₂₃H₂₀O₅S
• 分子量: 408.475
• InChiKey: ZDHYKZYFYJWVDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9,10-dimethoxyanthracene-2-sulphonyl chloride 、 苯甲醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以34.8%的产率得到benzyl 9,10-dimethoxyanthracene-2-sulphonate
  参考文献：
  名称：

  Photoinduced intramolecular electron transfer mechanism for photochemical dissociation of para-substituted benzyl 9,10-dimethoxyanthracene-2-sulfonates

  摘要：

  The photochemical behavior of para-substituted benzyl 9,10-dimethoxyanthracene-2-sulfonates with varying electron-withdrawing ability of substitutents has been investigated by both steady-state and laser flash photolysis techniques. p-Nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate is photochemically dissociated to give 9,10-dimethoxyanthracene-2-sulfonic acid, 9,10-dimethoxy-2-(p-nitrobenzyl)anthracene, and p,p'-dinitrobibenzyl which were assigned on the basis of mass spectroscopic data and H-1 NMR spectroscopy. Quantum yields for the photodissociation of p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate and for the formation of 9,10-dimethoxyanthracene-2-sulfonic acid with excitation at 436 nm in degassed acetonitrile solution are 0.12 +/- 0.03 and 0.10 +/- 0.03, respectively. Photodissociation of p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate is considered to proceed via an intramolecular electron transfer from the excited singlet state of 9,10-dimethoxyanthracene moiety to p-nitrobenzyl moiety followed by the heterolytic bond cleavage at oxygen-carbon bond of the sulfonyl ester from the fact that the transient absorptions at 310 and 425 nm due to 9,10-dimethoxyanthracene-2-sulfonate radical cation and around 340 nm due to p-nitrobenzyl radical anion are detected in laser spectroscopy. The rate constant for dissociation of p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate was determined to be (1.1 +/- 0.5) x 10(5) s-1 by kinetic analyses. Possible mechanisms for the photodissociation are discussed and it is concluded that the three factors which control the rate of photodissociation are intramolecular electron transfer, feasibility of oxygen-carbon bond scission, and stability of benzyl-type radical formed by the photodissociation.

  DOI：

  10.1021/j100180a046