(+/-)-7-(2,3-diacetoxypropyl)theophylline | 84414-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (+/-)-7-(2,3-diacetoxypropyl)theophylline
• 英文别名: 7-<2,3-Diacetoxy-propyl>-theophyllin；7-(2,3-diacetoxy-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione；7-(2,3-Diacetoxy-propyl)-1,3-dimethyl-3,7-dihydro-purin-2,6-dion；[2-Acetyloxy-3-(1,3-dimethyl-2,6-dioxopurin-7-yl)propyl] acetate
• CAS: 84414-71-1
• 化学式: C₁₄H₁₈N₄O₆
• 分子量: 338.32
• InChiKey: JTAQKTWSHNSLPK-UHFFFAOYSA-N

物化性质

• 沸点：
  542.4±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+/-)-7-(2,3-diacetoxypropyl)theophylline 在 溴 作用下， 生成 8-bromo-7-(2,3-diacetoxy-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  Satoda et al., Yakugaku Kenkyu, 1956, vol. 28, p. 609,611, 612

  摘要：

  DOI：
• 作为产物：
  描述：

  二羟丙茶碱 、 乙酸酐 反应 8.0h， 以99%的产率得到(+/-)-7-(2,3-diacetoxypropyl)theophylline
  参考文献：
  名称：

  Synthesis and characterization of hydrophilic theophylline base compounds and their use as ligands in the microwave assisted Suzuki–Miyaura couplings of halopyridines in water

  摘要：

  Xanthine derivatives, caffeine (L1), theobromine (L2), theophylline (L3), 7-(beta-hydroxyethyltheophylline) (L4), (7-(2,3-dihydroxypropyl)theophylline) (L5), and theophylline 7-acetic acid (L6) and the acetylated derivatives of the later three (L7-L9) were employed as ligands for the in situ palladium catalyzed Suzuki-Miyaura cross couplings of a series of halogenated pyridines. Optimized conditions were found where the diacetylated ligand (1.8) was determined to be the best for this process, producing good to excellent yields in the couplings of halogenated anilines with phenylboronic acid under mild reaction conditions in water using microwave irradiation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.103
• 作为试剂：
  描述：

  2-氯吡啶 、 苯硼酸 在 (+/-)-7-(2,3-diacetoxypropyl)theophylline 、 palladium diacetate 、 lithium carbonate 作用下， 以 水 为溶剂， 反应 0.17h， 生成 2-苯基吡啶 、 联苯
  参考文献：
  名称：

  Synthesis and characterization of hydrophilic theophylline base compounds and their use as ligands in the microwave assisted Suzuki–Miyaura couplings of halopyridines in water

  摘要：

  Xanthine derivatives, caffeine (L1), theobromine (L2), theophylline (L3), 7-(beta-hydroxyethyltheophylline) (L4), (7-(2,3-dihydroxypropyl)theophylline) (L5), and theophylline 7-acetic acid (L6) and the acetylated derivatives of the later three (L7-L9) were employed as ligands for the in situ palladium catalyzed Suzuki-Miyaura cross couplings of a series of halogenated pyridines. Optimized conditions were found where the diacetylated ligand (1.8) was determined to be the best for this process, producing good to excellent yields in the couplings of halogenated anilines with phenylboronic acid under mild reaction conditions in water using microwave irradiation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.103

文献信息

• El Ashry, El Sayed H.; Rashed, Nagwa; Awad, Laila F., Journal of Chemical Research, Miniprint, 2001, # 4, p. 440 - 450
  作者：El Ashry, El Sayed H.、Rashed, Nagwa、Awad, Laila F.、Abdel-Rahman, Adel A. H.、Rasheed, Hanna A.

  DOI：——

  日期：——
• Satoda et al., Yakugaku Kenkyu, 1956, vol. 28, p. 609,611, 612
  作者：Satoda et al.

  DOI：——

  日期：——
• Synthesis and characterization of hydrophilic theophylline base compounds and their use as ligands in the microwave assisted Suzuki–Miyaura couplings of halopyridines in water
  作者：Patricia Conelly-Espinosa、Ruben A. Toscano、David Morales-Morales

  DOI：10.1016/j.tetlet.2014.08.103

  日期：2014.10

  Xanthine derivatives, caffeine (L1), theobromine (L2), theophylline (L3), 7-(beta-hydroxyethyltheophylline) (L4), (7-(2,3-dihydroxypropyl)theophylline) (L5), and theophylline 7-acetic acid (L6) and the acetylated derivatives of the later three (L7-L9) were employed as ligands for the in situ palladium catalyzed Suzuki-Miyaura cross couplings of a series of halogenated pyridines. Optimized conditions were found where the diacetylated ligand (1.8) was determined to be the best for this process, producing good to excellent yields in the couplings of halogenated anilines with phenylboronic acid under mild reaction conditions in water using microwave irradiation. (C) 2014 Elsevier Ltd. All rights reserved.