5-chloro-2-hydroxy-3-iodo acetophenone | 175655-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-2-hydroxy-3-iodo acetophenone
• 英文别名: 1-(5-Chloro-2-hydroxy-3-iodophenyl)ethan-1-one；1-(5-chloro-2-hydroxy-3-iodophenyl)ethanone
• CAS: 175655-11-5
• 化学式: C₈H₆ClIO₂
• 分子量: 296.492
• InChiKey: SALFGYSMPWNVQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  89°C
• 沸点：
  296.7±40.0 °C(Predicted)
• 密度：
  1.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 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-chloro-2-hydroxy-3-iodo acetophenone 在 一水合肼 、 potassium hydroxide 作用下， 反应 1.0h， 生成 2-(5-(2-butyl-4-chloro-1H-imidazol-5-yl)-1H-pyrazol-3-yl)-4-chloro-6-iodophenol
  参考文献：
  名称：

  Konda, Shankaraiah G.; Dawane, Bhaskar S., Indian Journal of Heterocyclic Chemistry, 2010, vol. 20, # 2, p. 153 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-5-氯苯乙酮 在 水 、 碘 、 碘酸 作用下， 反应 0.5h， 以86%的产率得到5-chloro-2-hydroxy-3-iodo acetophenone
  参考文献：
  名称：

  一种简单高效的碘法和碘酸研磨法对羟基化芳族醛和酮进行无溶剂碘化的方法

  摘要：

  通过在室温下在无溶剂条件下研磨，使用固态的碘和碘酸对羟基化的芳族醛和酮进行绿色，温和且有效的碘化。该方法具有许多优点，例如环境友好，反应时间短，产率高，无害且后处理程序简单。

  DOI：

  10.1016/j.cclet.2010.04.008

文献信息

• A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid
  作者：Avinash T. Shinde、Sainath B. Zangade、Shivaji B. Chavan、Archana Y. Vibhute、Yogesh S. Nalwar、Yeshwant B. Vibhute

  DOI：10.1080/00397910903457332

  日期：2010.11.3

  This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product.

  本文介绍了使用碘和碘酸在乙醇中作为溶剂对不同芳香胺、羟基芳香醛、羟基苯乙酮和苯酚进行碘化的简单有效方法。显着的优点是反应条件温和，无需催化剂，反应时间短，操作简单，产品收率高。
• Poly(ethylene glycol) (PEG-400) as an alternative reaction solvent for the synthesis of some new 1-(4-(4′-chlorophenyl)-2-thiazolyl)-3-aryl-5-(2-butyl-4-chloro-1H-imidazol-5yl)-2-pyrazolines and their in vitro antimicrobial evaluation
  作者：Bhaskar S. Dawane、Shankaraiah G. Konda、Gajanan G. Mandawad、Baseer M. Shaikh

  DOI：10.1016/j.ejmech.2009.10.015

  日期：2010.1

  loro-1H-imidazol-5yl)-2-pyrazoline derivatives were prepared by the base catalyzed treatment of appropriate chalcones with 4-(4′-chlorophenyl)-2-hydrazino-thiazole in poly (ethylene glycol) (PEG-400) as an alternative reaction solvent. All the synthesized compounds were tested for their antimicrobial activities against Escherichia coli (MTCC 2939), Salmonella typhi (MTCC 98), Staphylococcus aureus

  通过该碱制备了几种1-（4-（4'-氯苯基）-2-噻唑基）-3-芳基-5-（2-丁基-4-氯-1 H-咪唑-5基）-2-吡唑啉衍生物用4-（4'-氯苯基）-2-肼基噻唑在聚乙二醇（PEG-400）中作为替代反应溶剂催化处理合适的查耳酮。测试所有合成的化合物对大肠杆菌（MTCC 2939），鼠伤寒沙门氏菌（MTCC 98），金黄色葡萄球菌（MTCC 96），枯草芽孢杆菌（MTCC 441），黑曲霉（MTCC 281），黑木霉（MTCC ）的抗菌活性167），产黄青霉（MTCC 160），镰刀菌（Fusarium moniliforme）（MTCC 156）和白色念珠菌（MTCC 183）。大多数化合物显示出有效的抗菌和抗真菌活性。
• Pyridinium Iodochloride: An Efficient Reagent for Iodination of Hydroxylated Aromatic Ketones and Aldehydes
  作者：Sandeep V. Khansole、Shyam S. Mokle、Mudassar A. Sayyed、Yeshwant B. Vibhute

  DOI：10.1002/jccs.200800130

  日期：2008.8

  Direct iodination of several reactive aromatic compounds like hydroxy substituted acetophenones and aldehydes with pyridinium iodochloride (PyICI) proceeded smoothly to afford the corresponding aromatic iodides in good to excellent yield. Pyridinium iodochloride has been found to be an efficient solid iodinating reagent with no hazardous effect and it can be handled safely.

  用碘氯化吡啶鎓 (PyICI) 对几种反应性芳族化合物（如羟基取代的苯乙酮和醛）进行直接碘化反应顺利进行，以良好至优异的收率得到相应的芳族碘化物。碘氯化吡啶鎓已被发现是一种有效的固体碘化试剂，没有有害影响，并且可以安全处理。
• An efficient one-pot synthesis of some new 2,4-diaryl pyrido[3,2-c]coumarins as potent antimicrobial agents
  作者：Bhaskar S. Dawane、Shankaraiah G. Konda、Ragini G. Bodade、Raghunath B. Bhosale

  DOI：10.1002/jhet.234

  日期：——

  Poly(ethylene glycol) (PEG-400) has been used as sustainable, nonvolatile, and environmental friendly reaction solvent for the synthesis of title compounds. Various diaryl pyrido[3,2-c]coumarins have been synthesized in one step by reacting 4-hydroxy-7-methyl-coumarin with α,β-unsaturated ketones in the presence of ammonium acetate. Further, in vitro antimicrobial (antibacterial and antifungal) activities

  聚乙二醇（PEG-400）已用作合成标题化合物的可持续，不挥发且环境友好的反应溶剂。通过一步反应合成了各种二芳基吡啶并[3,2-c]香豆素在存在以下条件下具有α，β-不饱和酮的4-羟基-7-甲基香豆素醋酸铵。此外，针对不同的病原体筛选了化合物的体外抗菌（抗菌和抗真菌）活性。结果表明，它们大多数显示出有效的活性。J.杂环化​​学。（2010）。
• Design, synthesis and biological studies of Survivin Dimerization Modulators that prolong mitotic cycle
  作者：Somsundaram N. Chettiar、James V. Cooley、In-Hee Park、Deepak Bhasin、Arnab Chakravarti、Pui-Kai Li、Chenglong Li、Naduparambil Korah Jacob

  DOI：10.1016/j.bmcl.2013.07.034

  日期：2013.10

  Survivin, a member of the inhibitor of apoptosis protein (IAP) family proteins, has essential roles in cell division and inhibition of apoptosis. Several clinical studies in cancer patients have shown that the elevated levels of survivin correlate with aggressiveness of the disease and resistance to radiation and chemotherapeutic treatments. Survivin is an integral component of chromosomal passenger complex (CPC) where it binds to borealin and INCENP through its dimerization interface. Thus, disruption of functional survivin along its dimer interface with a small molecule is hypothesized to inhibit the proliferation of cancer cells and sensitize them to therapeutic agents and radiation. Recently, a small molecule (Abbott8) was reported to bind at the dimerization interface of survivin. Further development of this compound was accomplished by computational modeling of the molecular interactions along the dimerization interface, which has led to the design of promising survivin dimerization modulators. Two of the most potent survivin modulators, LLP3 and LLP9 at concentrations between 50 and 100 nM, caused delay in mitotic progression and major mitotic defects in proliferating human umbilical vein endothelial cells (HUVEC) and prostate cancer cells (PC3). (C) 2013 Elsevier Ltd. All rights reserved.