5-溴-3-(氯甲基)-2-羟基苯甲醛 | 860798-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-溴-3-(氯甲基)-2-羟基苯甲醛
• 英文名称: 3-chloromethyl-5-bromosalicylaldehyde
• 英文别名: 2-hydroxy-3-chloromethyl-5-bromobenzaldehyde；5-Bromo-3-(chloromethyl)-2-hydroxybenzaldehyde；5-bromo-3-(chloromethyl)-2-hydroxybenzaldehyde
• CAS: 860798-79-4
• 化学式: C₈H₆BrClO₂
• 分子量: 249.491
• InChiKey: MMCCSHFZDDRLLM-UHFFFAOYSA-N

物化性质

• 沸点：
  318.4±42.0 °C(Predicted)
• 密度：
  1.739±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-3-(氯甲基)-2-羟基苯甲醛 、 3,3'-(乙烯二亚胺)二丙腈 在 sodium carbonate 作用下， 以 1,3-二氧戊环 为溶剂， 反应 6.0h， 以91%的产率得到1,6-bis(2-cyanoethyl)-2,5-bis(2-hydroxy-3-formyl-5-bromobenzyl)-2,5-diazahexane
  参考文献：
  名称：

  源自具有两个配位位点的不对称大环配体的同质和异质核配合物：去除悬臂和环化时铜离子的迁移

  摘要：

  在环化过程中，铜 (II) 从 N(胺)2O2 迁移到 N(亚胺)2O2 配位位点，丙腈悬臂之一被移除。异双核配合物[ZnL2Cu(OAc)]+是通过金属转移反应制备的。表征结果表明，这两种金属离子由两个酚氧原子和一个乙酸酯基团桥接，为这两种金属提供扭曲的五坐标几何结构。

  DOI：

  10.1080/00958972.2012.687103
• 作为产物：
  描述：

  聚合甲醛 、 5-溴水杨醛 在 盐酸 作用下， 生成 5-溴-3-(氯甲基)-2-羟基苯甲醛
  参考文献：
  名称：

  筛选 DFP 和对氧磷抑制乙酰胆碱酯酶的有效水杨醛肟再激活剂

  摘要：

  之前我们报道了两种水杨醛肟缀合物（L7R3和L7R5），与奥比肟和HI-6相比，对有机磷神经毒剂和农药抑制的乙酰胆碱酯酶表现出相同甚至更高的再激活效率。在这项研究中，选择L7R3和L7R5作为先导化合物，并采用基于片段的药物设计策略进行精制，总共构建了32种新型水杨醛肟缀合物，并筛选了DFP和对氧磷抑制乙酰胆碱酯酶的活性。研究结果表明，与奥比肟和 HI-6 相比，含有 4-硝基苯基的缀合物 L73R3 对对氧磷抑制的乙酰胆碱酯酶表现出更高的再激活功效。已证实4-吡啶基或4-硝基苯基外围位点配体、哌嗪连接体和甲基或氯取代的水杨醛肟的组合可以构建有效的非季铵肟再活化剂。研究结果有望开发出新一代高效有机磷中毒解毒剂。

  DOI：

  10.1039/d3md00628j

文献信息

• Synthesis, characterization, crystal structure and antimicrobial activities of new trans N,N-substituted macrocyclic dioxocyclam and their copper(II) and nickel(II) complexes
  作者：G. Nirmala、A. Kalilur Rahiman、S. Sreedaran、R. Jegadeesh、N. Raaman、V. Narayanan

  DOI：10.1016/j.poly.2010.09.036

  日期：2011.1

  (L5) were synthesized. The ligands were characterized by elemental analysis, FT IR, 1H NMR and mass spectrometry studies. The crystal structure of L1 is also reported. The copper(II) and nickel(II) complexes of these ligands were prepared and characterized by elemental analysis, FT IR, UV–Vis and mass spectral studies. The cyclic voltammogram of the complexes of ligand L1–3 show one-electron quasi-reversible

  摘要新的反式二取代大环配体1,8- [N，N-双（3-甲酰基-12-羟基-5-甲基）苄基] -5,12-二氧代-1,4,8,11-四氮杂环十四烷（ L1），1,8- [N，N-双（3-甲酰基-12-羟基-5-溴）苄基] -5,12-二氧代-1,4,8,11-四氮杂环十四烷（L2），N， N-双[1,8-二苯甲酰基] -5,12-二氧代-1,4,8,11-四氮杂环十四烷（L3），N，N-双[1,8-（2-硝基苯甲酰基）]-5,12 -dioxo-1,4,8,11-四氮杂十四烷（L4）和N，N-双[1,8-（4-硝基苯甲酰基）]-5,12-dioxo-1,4,8,11-四氮杂十四烷（ L5）被合成。通过元素分析，FT IR，1H NMR和质谱研究对配体进行表征。还报道了L1的晶体结构。制备了这些配体的铜（II）和镍（II）配合物，并通过元素分析，FT IR，UV-Vis和质谱研究对其进行了表征
• Design, synthesis and evaluation of new classes of nonquaternary reactivators for acetylcholinesterase inhibited by organophosphates
  作者：Zhao Wei、Huanglei Bi、Yan-qin Liu、Hui-fang Nie、Lin Yao、Sheng-zheng Wang、Jun Yang、Yong-an Wang、Xueying Liu、Zhi-bing Zheng

  DOI：10.1016/j.bioorg.2018.09.025

  日期：2018.12

  for reactivation of both nerve agents and pesticides inhibited hAChE were described in this paper. It was found that substituted salicylaldehydes conjugated to aminobenzamide through piperidine would produce efficient reactivators for sarin, VX and tabun inhibited hAChE, such as L6M1R3, L6M1R5 to L6M1R7, L4M1R3 and L4M1R5 to L4M1R7. The in vitro reactivation experiment for pesticides inhibited hAChE

  本文描述了一系列新的非季铵盐共轭物，用于神经活性剂和农药抑制hAChE的活化。发现通过哌啶与氨基苯甲酰胺缀合的取代的水杨醛将产生沙林，VX和塔宾抑制的hAChE的有效活化剂，例如L6M1R3，L6M1R5至L6M1R7，L4M1R3和L4M1R5至L4M1R7。在体外首次进行了农药抑制hAChE的复活实验。尽管它们的效率不如奥比多肟，但与2-PAM相比，它们中的一些被认为是同等或更有效的再活化剂。发现在大多数情况下，引入外围位点配体可以增加肟对抑制的hAChE的结合亲和力，从而导致更大的再活化能力。
• The one-pot halomethylation of 5-substituted salicylaldehydes as convenient precursors for the preparation of heteroditopic ligands for the binding of metal salts
  作者：Qiang Wang、Claire Wilson、Alexander J. Blake、Simon R. Collinson、Peter A. Tasker、Martin Schröder

  DOI：10.1016/j.tetlet.2006.09.149

  日期：2006.12

  The one-pot bromo- and chloro-methylation of various 5-substituted salicylaldehydes with paraformaldehyde and hydrobromic or hydrochloric acid has been achieved. This approach establishes a convenient and flexible method to attach functional arms to salicylaidehydes for further applications in organic and coordination chemistry. Examples are described using 3-bromomethyl-5-t-butylsalicylaldehyde in the synthesis of piperazine-containing heteroditopic ligands as receptors for metal salts. (c) 2006 Elsevier Ltd. All rights reserved.
• Conjugates of salicylaldoximes and peripheral site ligands: Novel efficient nonquaternary reactivators for nerve agent-inhibited acetylcholinesterase
  作者：Zhao Wei、Yan-qin Liu、Sheng-zheng Wang、Lin Yao、Hui-fang Nie、Yong-an Wang、Xue-Ying Liu、Zhi-bing Zheng、Song Li

  DOI：10.1016/j.bmc.2017.06.041

  日期：2017.8

  A new family of nonquaternary reactivators for nerve agent-inhibited human acetylcholinesterase (hAChE) were designed, synthesized and tested in this paper. It was found that salicylaldoximes were able to quickly cleave the P-S bond of organophosphate and avoid the reinhibition phenomenon in the reactivation process, but they lacked reactivating ability due to poor affinity for AChE. Based on a dual site binding strategy, different peripheral site ligands of AChE were introduced to achieve extra affinity. The in vitro reactivation experiments demonstrated that some of the yielding conjugates exhibited similar or even superior ability to reactivate sarin-, VX- or tabun-inhibited hAChE in comparison with the mono-and bis-pyridinium aldoximes currently used. Moreover, due to greatly improved lipophilicity, these nonquaternary conjugates hold promise for the development of efficient centrally activating reactivators. (C) 2017 Elsevier Ltd. All rights reserved.
• Homo and heterodinuclear complexes derived from unsymmetrical macrocyclic ligands with two coordination sites: removal of a pendant arm and migration of copper ion upon cyclization
  作者：Hamid Golchoubian、Davood Sadeghi Fateh、Giuseppe Bruno、Hadi Amiri Rudbari

  DOI：10.1080/00958972.2012.687103

  日期：2012.6.10

  copper(II) migrates from the N(amine)2O2 to the N(imine)2O2 coordination site and one of the propionitrile pendant arms is removed. The heterodinuclear complexes [ZnL2Cu(OAc)]+ were prepared by a transmetallation reaction. The characterization results showed that the two metal ions are bridged by two phenolic oxygen atoms and an acetate group, providing distorted five-coordinate geometries for both metals.

  在环化过程中，铜 (II) 从 N(胺)2O2 迁移到 N(亚胺)2O2 配位位点，丙腈悬臂之一被移除。异双核配合物[ZnL2Cu(OAc)]+是通过金属转移反应制备的。表征结果表明，这两种金属离子由两个酚氧原子和一个乙酸酯基团桥接，为这两种金属提供扭曲的五坐标几何结构。