2-(2,4-二氯苯基)-4,5-二氢-1H-咪唑 | 61033-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2,4-二氯苯基)-4,5-二氢-1H-咪唑
• 英文名称: 2-(2,4-dichlorophenyl)-2-imidazoline
• 英文别名: 2-(2,4-dichlorophenyl)imidazoline；2-(2,4-dichloro-phenyl)-4,5-dihydro-1H-imidazole；2-(2,4-Dichlorphenyl)-Δ²-imidazolin；2-(2,4-dichlorophenyl)-4,5-dihydro-1H-imidazole
• CAS: 61033-72-5
• 化学式: C₉H₈Cl₂N₂
• 分子量: 215.082
• InChiKey: DSQMJENLNWSEMO-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  156-158 °C(Press: 4 Torr)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-[(2,4-dichlorophenyl)methylideneamino]ethanamine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 反应 0.2h， 生成 2-(2,4-二氯苯基)-4,5-二氢-1H-咪唑
  参考文献：
  名称：

  Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors

  摘要：

  A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO) 2-3,4-Ph; (MeO)(3)-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl-2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.001

文献信息

• Semi-Empirical Computation on Mechanism of Imidazolines and Benzimidazoles Synthesis and Their QSAR Studies
  作者：Swapnali Hazarika、Dilip Konwar、Manas Jyoti Bora

  DOI：10.14233/ajchem.2014.16320

  日期：——

  A green, mild and anaerobic synthesis of imidazolines and benzimidazoles from aldehydes and diamines using I2/KI/K2CO3/H2O system has been investigated by semi-empirical methods. The observed efficient direction of the above synthesis has been modeled from a comparison of the energies of four possible transition states arising from mono and di additions of iodines in the configured molecules. In the reaction I1 B is the most favorable transition state [TS] which is shown to be 20 Kcal/mol by PM3 analyses. The resulting trends of relative transition states energies are in excellent agreement with the experimental observations. Also, the bond order, bond length, heat of formation is in good agreement to the formation of product B. In order to establish the suitable mechanism of the reaction a quantitative structure activity relationship analysis has been made using hydrophobicity as the molecular descriptor. In this analysis the values of refractivity, polarizability, hydration energy, electron affinity, ionization potential and dipole moment of the compounds have been correlated with their hydrophobicity which has been taken as the molecular property.

  通过半经验方法研究了在I2/KI/K2CO3/H2O体系下，使用醛和二胺进行绿色、温和且厌氧的咪唑啉和苯并咪唑合成。通过比较四种可能的过渡状态的能量——源自配置分子中单加和双加碘——来模拟上述合成的高效方向。在反应I1中，B是最佳过渡态[TS]，PM3分析显示其能量为20千卡/摩尔。相对过渡态能量的趋势与实验观察结果非常吻合。此外，键级、键长和生成热都与产物B的生成一致。为了确定反应的适宜机理，使用疏水性作为分子描述符进行了定量结构活性关系分析。在此分析中，化合物折射率、极化率、水合能、电子亲和力、电离势和偶极矩的值与其疏水性相关联，作为分子属性。
• An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon–nitrogen bonds in water
  作者：Pranjal Gogoi、Dilip Konwar

  DOI：10.1016/j.tetlet.2005.10.134

  日期：2006.1

  The system, I2/KI/K2CO3/H2O, oxidizes carbon–nitrogen bonds for the synthesis of imidazolines and benzimidazoles from aldehydes and diamines under anaerobic conditions in water at 90 °C with excellent yields. The process is green, mild and inexpensive.

  I 2 / KI / K 2 CO 3 / H 2 O系统在90°C的水中厌氧条件下，通过醛和二胺氧化碳-氮键，以从醛和二胺合成咪唑啉和苯并咪唑，并具有出色的收率。该过程绿色，温和且便宜。
• Efficient Synthesis of 2-Imidazolines in the Presence of Molecular Iodine Under Ultrasound Irradiation
  作者：Guo-Feng Chen、Hong-Yang Li、Nan Xiao、Bao-Hua Chen、Ya-Li Song、Ji-Tai Li、Zhi-Wei Li

  DOI：10.1071/ch13700

  日期：——

  An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25–30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.

  本研究介绍了一种高效的单锅合成工艺，该工艺在 25-30°C 超声波照射下，使用分子碘和碳酸钾在绝对乙醇中以醛和乙二胺为原料制备 2-咪唑啉。该合成策略具有以下优点：条件温和、成本要求低、催化剂容易获得、反应时间短、操作简单以及良好的收率。
• A Facile and Efficient Synthesis of 2-Imidazolines from Aldehydes Using Hydrogen Peroxide and Substoichiometric Sodium Iodide
  作者：Guo-yi Bai、Kai Xu、Guo-feng Chen、Yong-hui Yang、Tian-yu Li

  DOI：10.1055/s-0030-1259992

  日期：2011.5

  The reaction of aldehydes with ethylenediamine for the preparation of 2-imidazolines has been studied using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate. A mild, green, and efficient method is established to carry out this reaction in high yield. 2-imidazoline - hydrogen peroxide - aldehydes - ethylenediamine - environmentally friendly process

  在碘化钠和无水硫酸镁存在下，使用过氧化氢作为氧化剂，已经研究了醛与乙二胺反应制备2-咪唑啉的反应。建立了温和，绿色和有效的方法以高产率进行该反应。 2-咪唑啉-过氧化氢-醛-乙二胺-环保工艺
• Green Synthesis of 2‐Substituted Imidazolines using Hydrogen Peroxide Catalyzed by Tungstophosphoric Acid and Tetrabutylammonium Bromide in Water
  作者：Shuai Liu、Wang Li、Yiying Pang、Hesheng Xiao、Yi Zhou、Xiaoji Wang

  DOI：10.1002/jhet.3482

  日期：2019.3

  Various 2‐substituted imidazolines were constructed from aromatic aldehydes with ethylenediamine using hydrogen peroxide as an oxidant in water. Tungstophosphoric acid (HPW) was found to be active for this transformation due to its ubiquitous catalytic and oxidative nature, and further combination of tetrabutylammonium bromide (TBAB) made this transformation more efficient and attractive. It was found

  使用过氧化氢在水中作为氧化剂，由芳族醛与乙二胺合成了各种2取代的咪唑啉。钨磷酸（HPW）由于其无处不在的催化和氧化性质而被发现对这种转化具有活性，并且四丁基溴化铵（TBAB）的进一步组合使这种转化更加有效和引人注目。发现相应的2-取代的咪唑啉的收率受到苯环上取代基的位置和性质的显着影响。还提出了合理的机制来阐明该催化氧化系统。