1-(2-羟乙基)-3-甲基氯化咪唑 | 67029-87-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(2-羟乙基)-3-甲基氯化咪唑
• 英文名称: 1-(2-hydroxy-5-methoxyphenyl)-3-phenylpropane-1,3-dione
• CAS: 67029-87-2
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: BLZXDUVTDYZVNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  42-44 °C
• 沸点：
  460.0±35.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-羟乙基)-3-甲基氯化咪唑 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以58%的产率得到5-(2-羟基-5-甲氧基苯基)-3-苯基吡唑
  参考文献：
  名称：

  Design, synthesis and structure–activity relationships of 3,5-diaryl-1H-pyrazoles as inhibitors of arylamine N-acetyltransferase

  摘要：

  The synthesis and inhibitory potencies of a novel series of 3,5-diaryl-1H-pyrazoles as specific inhibitors of prokaryotic arylamine N-acetyltransferase enzymes is described. The series is based on hit compound 1 3,5-diaryl-1H-pyrazole identified from a high-throughout screen that has been carried out previously and found to inhibit the growth of Mycobacterium tuberculosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.052
• 作为产物：
  描述：

  4-methoxyphenyl 3-(ethylenedioxy)-3-phenylpropanoate 在 硫酸 、 silica gel 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 12.0h， 生成 1-(2-羟乙基)-3-甲基氯化咪唑
  参考文献：
  名称：

  Garcia, Hermenegildo; Iborra, Sara; Miranda, Miguel A., Heterocycles, 1986, vol. 24, # 9, p. 2511 - 2517

  摘要：

  DOI：

文献信息

• Rh(III)‐Catalyzed Aldehydic C−H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
  作者：Guo‐Dong Xu、Kenneth L. Huang、Zhi‐Zhen Huang

  DOI：10.1002/adsc.201900276

  日期：2019.7.11

  A novel aldehydic C−H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)−H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C−H functionalization

  在铑（III）催化下，开发了水杨醛与亚磺酰之间的新型醛C-H官能化反应，可提供中等至良好收率的偶联产物。还提出了一种可能的机理，该机理涉及通过铑（III）和铑（III）催化的卡宾插入而使醛类的C（sp 2）-H活化。还发现醛化的CH功能化然后脱水环化能够在一锅中产生类黄酮。
• An Efficient and Green Synthesis of Flavones Using Natural Organic Acids as Promoter Under Solvent-free Condition
  作者：Nitin M. Thorat、Santosh R. Kote、Shankar R. Thopate

  DOI：10.2174/157017861108140613163214

  日期：2014.6

  An efficient and eco-friendly synthesis of flavones, promoted by naturally occurring acids, via cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones using conventional and microwave heating under solvent-free condition is described.

  描述了通过使用常规和微波加热在无溶剂条件下对1-（2-羟苯基）-3-芳基-1,3-丙二酮进行环脱水作用，由天然存在的酸促进的黄酮的高效和生态友好型合成。
• Trypanocidal Activity of Flavanone Derivatives
  作者：Gabriela Maciel Diogo、Josimara Souza Andrade、Policarpo Ademar Sales Junior、Silvane Maria Fonseca Murta、Viviane Martins Rebello Dos Santos、Jason Guy Taylor

  DOI：10.3390/molecules25020397

  日期：——

  rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology

  恰加斯病，也称为美洲锥虫病，被世界卫生组织列为被忽视的疾病。在临床治疗方面，目前市场上仅有苯硝唑和硝呋莫司两种药物上市，两者均推荐用于急性期，但慢性期治愈率较低。此外，强烈的副作用可能会导致停止这种治疗。面对这种情况，我们报告了 3-苯甲酰基-黄烷酮的合成和杀锥虫活性。在 3 步合成过程中以令人满意的产率制备了新型 3-苯甲酰基-黄烷酮衍生物。根据推荐的指南，使用了基于全细胞的筛选方法，允许同时使用导致人类感染的两种寄生虫形式。
• L-Ascorbic Acid: A Green and Competent Promoter for Solvent-Free Synthesis of Flavones and Coumarins under Conventional as well as Microwave Heating
  作者：Rohit Arvind Dengale、Nitin Madhu Thorat、Shankar Ramchandra Thopate

  DOI：10.2174/1570178614666161116125148

  日期：2017.1.3

  Background: An expeditious approach has been developed for the synthesis of two distinct classes of benzopyrones viz. flavones and coumarins under solvent-free conditions. L-Ascorbic acid was found to be an effective promoter under microwave irradiation and conventional heating. Various benzo-α-pyrones and benzo-γ-pyrones were synthesized with overall good yields. The present protocol is highly facile and needs

  背景：已经开发出一种快速的方法来合成两种不同类别的苯并吡喃酮。无溶剂条件下的黄酮和香豆素。发现L-抗坏血酸在微波辐射和常规加热下是有效的促进剂。合成了各种苯并-α-吡喃酮和苯并-γ-吡喃酮，总收率良好。本方案非常容易，不需要柱色谱法纯化，因此在微波辐射和常规加热下均可作为一种有效且兼容的方法。 结果：研究了L-抗坏血酸对黄酮和香豆素合成的催化能力。为此目的，选择了1-（2-羟苯基）-3-芳基-1，3-丙二酮的环脱水和Pechmann香豆素的合成反应。因此，据观察，完成反应需要一摩尔的L-抗坏血酸。在所有情况下，都能以良好至极佳的收率顺利产生所需的黄酮。表明其对各种官能团的优异耐受性。但是，在这些条件下，给电子基团有利于香豆素的合成。仔细分析了所有反应混合物，核磁共振表明转化率高，没有副产物。 结论：我们已经开发了L-抗坏血酸促进的，无溶剂的简单方法，该方法在微波辐射下以及常规加热条件下合成
• Microwave Assisted Efficient Synthesis of Flavone using ZnO Nanoparticles as Promoter under Solvent-Free Conditions
  作者：Pradip J. Unde、Nitin M. Thorat、Limbraj R. Patil

  DOI：10.14233/ajchem.2019.21873

  日期：2019.4.15

  A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.

  在无溶剂条件下，利用ZnO纳米颗粒作为促进剂，在热和微波辐射下，从1-(2-羟基苯基)-3-芳基-1,3-丙二酮合成黄酮类化合物的简单且高效的合成方案已被证明。该催化剂价格低廉、稳定，可轻松回收/重复使用多个周期，并且观察到几乎相同的产率，证实了催化剂的稳定性。相信这种方法将成为传统反应的替代途径。因为在这种方案中，产率相当高，反应时间短，工作简单，催化剂可回收并且在工作过程中不会产生任何有害副产物。