5-chloro-4-hydroxyisophthalaldehyde | 3328-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-4-hydroxyisophthalaldehyde
• 英文别名: 5-Chloro-4-hydroxy-1,3-benzenedicarboxaldehyde；5-chloro-4-hydroxybenzene-1,3-dicarbaldehyde
• CAS: 3328-72-1
• 化学式: C₈H₅ClO₃
• 分子量: 184.579
• InChiKey: DUDHVHOOHGWHCN-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C(Solv: water (7732-18-5))
• 沸点：
  265.9±40.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-chloro-4-hydroxyisophthalaldehyde 生成 5-chloro-4-hydroxy-isophthalaldehyde-disemicarbazone
  参考文献：
  名称：

  Hanus, Journal fur praktische Chemie (Leipzig 1954), 1941, vol. <2> 158, p. 245,250

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氯苯酚 在 sodium hydroxide 作用下， 生成 5-chloro-4-hydroxyisophthalaldehyde
  参考文献：
  名称：

  Hanus, Journal fur praktische Chemie (Leipzig 1954), 1941, vol. <2> 158, p. 245,250

  摘要：

  DOI：

文献信息

• Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction
  作者：Xue-wen Fu、Wen-chen Pu、Guo-lin Zhang、Chun Wang

  DOI：10.1007/s11164-014-1881-5

  日期：2015.11

  A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.

  一种铜介导的Duff反应已被开发，用于苯酚的邻位选择性甲酰化。在铜物种的存在下，Duff甲酰化的产率和邻位选择性得到了显著提高，这为从苯酚获得水杨醛提供了便捷的方法。
• Mechanochemical Duff Reaction in Solid Phase for Easy Access to Mono- and Di-formyl Electron-Rich Arenes
  作者：Soumik Saha、Akhil A. Bhosle、Amrita Chatterjee、Mainak Banerjee

  DOI：10.1021/acs.joc.3c00789

  日期：2023.7.21

  new mold of the mechanochemical Duff reaction. The mono-formyl phenols were obtained with exclusive ortho-selectivity, whereas unprecedented para-formylation was observed for other electron-rich aromatics. By controlling the stoichiometry of HMTA, the method offers easy access to di-formylated phenols as well. The scalability of the reaction was validated with selected substrates at the gram-scale level

  通过采用固相机械化学途径，开发了一种可持续的替代已有百年历史的达夫反应。使用六亚甲基四胺(HMTA)作为甲酰源和少量H 2 SO 4在混合研磨机中的组合，以二氧化硅作为固体反应介质，高收率地制备了一系列单甲酰基富电子芳烃。在机械化学达夫反应的新模具中，避免使用有毒、昂贵且低沸点的三氟乙酸。单甲酰基苯酚具有独特的邻位选择性，而其他富电子芳族化合物则观察到前所未有的对位甲酰化反应。通过控制 HMTA 的化学计量，该方法还可以轻松获得二甲酰化酚。使用选定的克级底物验证了反应的可扩展性。在一个案例研究中，探索了对甲氨基酚衍生物的合成中的机械化学串联反应。这种无溶剂、无金属的温和甲酰化方法无需繁琐的后处理步骤，并且使用廉价的无机酸缩短反应时间，是现有芳香族甲酰化方法的可持续替代方法。
• Hybrid benzofuran–bisindole derivatives: New prototypes with promising anti-hyperlipidemic activities
  作者：Koneni V. Sashidhara、Ram K. Modukuri、Ravi Sonkar、K. Bhaskara Rao、Gitika Bhatia

  DOI：10.1016/j.ejmech.2013.07.009

  日期：2013.10

  A series of different benzofuran bisindole hybrids were synthesized and evaluated in vitro for their antioxidant and in vivo for antidyslipidemic activity in triton WR-1339 induced hyperlipidemic rats. Among the series, compounds 4a, 4c, 4h and 4j showed significant decrease in plasma levels of total cholesterol (TC), phospholipids (PL) and triglycerides (TG) followed by increase in post heparin lipolytic activity (PHLA). In addition, the active hybrids possessed moderate antioxidant properties and increased the plasma lecithin cholesterol acyltransferase (LCAT) activity, which plays a key role in lipoprotein metabolism contributing to an increased level of HDL-C in serum. These results indicate that these hybrids constitute novel prototypes for the management of dyslipidemia. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Otsuka; Umezawa, 1950, vol. 3, # 9, p. 38,42
  作者：Otsuka、Umezawa

  DOI：——

  日期：——