6-bromo-8,9,10,11-tetrahydrotetracene-1,2-dicarboxylic anhydride | 1258786-15-0

• 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: 6-bromo-8,9,10,11-tetrahydrotetracene-1,2-dicarboxylic anhydride
• 英文别名: 12-Bromo-19-oxapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1,3,9,11,13(21),14,16-heptaene-18,20-dione；12-bromo-19-oxapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1,3,9,11,13(21),14,16-heptaene-18,20-dione
• CAS: 1258786-15-0
• 化学式: C₂₀H₁₃BrO₃
• 分子量: 381.225
• InChiKey: UNKNCFOXUAGCTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  草酰氯 、 6-bromo-1,2,3,4-tetrahydrotetracene 在 aluminum (III) chloride 、 双氧水 、 sodium hydroxide 、 硫酸 作用下， 以 二硫化碳 、 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 6-bromo-8,9,10,11-tetrahydrotetracene-1,2-dicarboxylic anhydride 、 8-bromo-3,4,5,6-tetrahydrotetracene-1,2-dicarboxylic anhydride
  参考文献：
  名称：

  Synthesis of functionalized tetracene dicarboxylic imides

  摘要：

  For the first time, a synthesis of tetracene dicarboxylic imides was established with 1,2,3,4-tetrahydrotetracene (1) instead of tetracene as the starting material. Mono-bromination of 1 by CuBr2 followed by a Friedel-Crafts reaction, oxidation, and imidization gave the tetrahydrotetracene carboxylic imides 5a-b. Subsequent oxidative dehydrogenation of 5a-b with DDQ afforded the functional tetracene dicarboxylic imide monobromides 6a-b. which can be further functionalized to provide functional materials such as the 'donor-acceptor' type compounds 7a-b. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.116

文献信息

• Synthesis of functionalized tetracene dicarboxylic imides
  作者：Jun Yin、Kai Zhang、Chongjun Jiao、Jinling Li、Chunyan Chi、Jishan Wu

  DOI：10.1016/j.tetlet.2010.09.116

  日期：2010.12

  For the first time, a synthesis of tetracene dicarboxylic imides was established with 1,2,3,4-tetrahydrotetracene (1) instead of tetracene as the starting material. Mono-bromination of 1 by CuBr2 followed by a Friedel-Crafts reaction, oxidation, and imidization gave the tetrahydrotetracene carboxylic imides 5a-b. Subsequent oxidative dehydrogenation of 5a-b with DDQ afforded the functional tetracene dicarboxylic imide monobromides 6a-b. which can be further functionalized to provide functional materials such as the 'donor-acceptor' type compounds 7a-b. (C) 2010 Elsevier Ltd. All rights reserved.