9,10-dimethoxy-2-(p-nitrobenzyl)anthracene | 132228-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dimethoxy-2-(p-nitrobenzyl)anthracene
• 英文别名: 9,10-Dimethoxy-2-[(4-nitrophenyl)methyl]anthracene
• CAS: 132228-29-6
• 化学式: C₂₃H₁₉NO₄
• 分子量: 373.408
• InChiKey: GBJWSONVCBCDHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulphonate 以 乙腈 为溶剂， 生成 4,4-二硝基联苄 、 2-(乙酰基氨基)-2-脱氧-4,6-二-O-硫代-D-半乳吡喃糖 、 9,10-dimethoxy-2-(p-nitrobenzyl)anthracene
  参考文献：
  名称：

  对-硝基苄基9,10-二甲氧基蒽-2-磺酸的光化学解离通过分子内电子转移

  摘要：

  尽管已知邻硝基苄基芳族磺酸盐通过分子内重排而光解离，但尚未报道对硝基硝基苯芳族磺酸盐的光解离。在这项研究中，我们报告说，对硝基苄基9,10-二甲氧基蒽-2-磺酸被光化学解离得到9,10-二甲氧基蒽-2-磺酸，9,10-二甲氧基-2-（对硝基苄基）-蒽，和p，p′-二硝基联苄基。该解离被认为是通过分子内电子从9,10-二甲氧基蒽部分转移至p进行的。-硝基苄基部分。乙腈中光解离的量子产率为0.11，光谱响应扩展至450 nm。量子产率比那些高得多ö硝基苄酯。

  DOI：

  10.1039/p29900001709

文献信息

• Photoinduced intramolecular electron transfer mechanism for photochemical dissociation of para-substituted benzyl 9,10-dimethoxyanthracene-2-sulfonates
  作者：Kazuhiko Naitoh、Koh Yoneyama、Tsuguo Yamaoka

  DOI：10.1021/j100180a046

  日期：1992.1

  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.