4-(2-iodoethyl)benzene-1,2-diol | 69690-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-iodoethyl)benzene-1,2-diol
• 英文别名: 4-(2-iodo-ethyl)-pyrocatechol；4-(2-Jod-aethyl)-brenzcatechin；3.4-Dihydroxy-1-(2-jod-aethyl)-benzol
• CAS: 69690-12-6
• 化学式: C₈H₉IO₂
• 分子量: 264.063
• InChiKey: JQLWPHJLGZAAKR-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C(Solv: water (7732-18-5))
• 沸点：
  365.8±32.0 °C(Predicted)
• 密度：
  1.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-iodoethyl)benzene-1,2-diol 在 吡啶 、 盐酸 作用下， 以 甲醇 、 水 、 丁酮 为溶剂， 反应 64.0h， 生成 1,2-dihydroxy-4-(2-mercaptoethyl)benzene
  参考文献：
  名称：

  Enhanced chemopreventive activity of hydroxytyrosol on HL60 and HL60R cells by chemical conversion into thio derivatives

  摘要：

  Thio derivatives of hydroxytyrosol containing thiol, thioacetate and disulfide functionalities were synthesized from natural hydroxytyrosol (3,4-DHPEA) via 3,4-dihydroxyphenethyl halides. These compounds, containing the combination of catechol moiety and divalent sulfur functions, were tested for the proapoptotic and anti-proliferative activities on both parental HL60 and multi-drug resistant HL60R cells. It was found that all synthesized compounds were more effective than 3,4-DHPEA in inducing apoptosis on HL60R cells, and that the hydroxytyrosol disulfide was the most active pro-apoptotic and anti-proliferative compound on both HL60 and HL60R cells. Different from 3,4-DHPEA, all thio derivatives of hydroxytyrosol induced apoptosis by a mechanism not involving the release of H2O2 in the culture medium. The data on HL60R cells suggest that these compounds could be able to reverse the resistance toward the most common drugs in cancer therapy. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2012.12.028
• 作为产物：
  描述：

  3,4-二甲氧基苯基乙酸乙酯 在 氢碘酸 、 sodium 、 xylene 作用下， 生成 4-(2-iodoethyl)benzene-1,2-diol
  参考文献：
  名称：

  Schoepf et al., Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 86,89

  摘要：

  DOI：

文献信息

• PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES
  申请人：National and Kapodistrian University of Athens

  公开号：EP3838885A1

  公开（公告）日：2021-06-23

  A process for the production of a compound according to Formula (I), such as oleocanthal or oleacein, starting from oleuropein. The process provides the dialdehyde core of oleocanthal, oleacein and their analogues having the required stereochemistry. Furthermore, the process can be used for the production of a large number of structurally diverse products by varying the structure of the alcohol moiety in the esterification step.

  一种以油黄素为原料生产符合式 (I) 的化合物（如油黄醛或油菜素）的工艺。该工艺可提供具有所需立体化学结构的油菜醛、油菜素及其类似物的二醛核心。此外，通过改变酯化步骤中醇分子的结构，该工艺还可用于生产大量结构不同的产品。