2-cyclohexylimidazoline | 67277-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 2-cyclohexylimidazoline
• 英文别名: 2-cyclohexyl-2-imidazoline；1H-Imidazole, 2-cyclohexyl-4,5-dihydro-；2-cyclohexyl-4,5-dihydro-1H-imidazole
• CAS: 67277-65-0
• 化学式: C₉H₁₆N₂
• 分子量: 152.239
• InChiKey: DHSHQQYSSXYLLK-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  116-118 °C(Press: 1 Torr)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-cyclohexylimidazoline 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-Cyclohexyliden-1,3-dimethylimidazolidin
  参考文献：
  名称：

  Gruseck, Ursula; Heuschmann, Manfred, Chemische Berichte, 1987, vol. 120, p. 2053 - 2064

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(cyclohexylmethylideneamino)ethanamine 在 次氯酸叔丁酯 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 生成 2-cyclohexylimidazoline
  参考文献：
  名称：

  用次氯酸叔丁酯从醛轻松制备 2-咪唑啉

  摘要：

  在次氯酸叔丁酯存在下，由醛和乙二胺高效、高产地制备 2-咪唑啉。通过该方法，可以直接由相应的二醛高收率地制备出作为手性配体的1,3-双(咪唑啉-2-基)苯和2,6-双(咪唑啉-2-基)吡啶。

  DOI：

  10.1055/s-2007-983726

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。
• Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and <i>N</i>-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10
  作者：Iraj Mohammadpoor-Baltork、Mohammad Abdollahi-Alibeik

  DOI：10.1139/v04-171

  日期：2005.2.1

  Different types of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines are efficiently oxidized to their corresponding imidazoles with potassium permanganate (KMnO₄) supported on montmorillonite K-10 under very mild conditions. The procedure is very simple and no strict conditions were required. Selective dehydrogenation of 2-alkyl-2-imidazolines in the presence of 2-aryl-2-imidazolines is a noteworthy advantage of this method and can be considered as a useful practical achievement in these reactions.Key words: 2-imidazolines, imidazoles, dehydrogenation, potassium permanganate, montmorillonite K-10.

  不同类型的2-咪唑啉、双咪唑啉和N-取代的2-咪唑啉可以在蒙脱石K-10载体上使用高锰酸钾(KMnO₄)在非常温和的条件下高效氧化为它们相应的咪唑化合物。该方法非常简单，无需严格条件。在2-芳基-2-咪唑啉存在时选择性脱氢2-烷基-2-咪唑啉是该方法的一个显著优势，可以被视为这些反应中的一项有用的实际成就。关键词：2-咪唑啉、咪唑化合物、脱氢、高锰酸钾、蒙脱石K-10。
• Novel, Mild and Chemoselective Dehydrogenation of 2-Imidazolines with Trichloroisocyanuric Acid
  作者：Iraj Mohammadpoor-Baltork、Mohammad Zolfigol、Mohammad Abdollahi-Alibeik

  DOI：10.1055/s-2004-835635

  日期：——

  A rapid, mild and high-yielding method for dehydrogenation of a variety of structurally diverse 2-imidazolines to imidazoles using trichloroisocyanuric acid (TCCA) in the presence of DBU is reported. Chemoselective oxidation of 2-imidazolines can be achieved in the presence of sulfide and alcohol. The mild conditions of this procedure and the absence of any transition metal make this reaction suitable for safe laboratory use.

  报道了一种快速、温和且高产的脱氢方法，使用三氯异氰尿酸（TCCA）在DBU的存在下，将多种结构多样的2-咪唑啉转化为咪唑。该方法能够在存在硫化物和醇的情况下实现选择性氧化2-咪唑啉。这一过程的温和条件以及不使用任何过渡金属，使得该反应适合安全的实验室使用。
• Alumina supported potassium permanganate: an efficient reagent for chemoselective dehydrogenation of 2-imidazolines under mild conditions
  作者：Mohammad Abdollahi-Alibeik、Iraj Mohammadpoor-Baltork、Mohammad Ali Zolfigol

  DOI：10.1016/j.bmcl.2004.09.070

  日期：2004.12

  Potassium permanganate supported on alumina was found to be an efficient reagent system for dehydrogenation of 2-imidazolines to imidazoles under mild conditions at room temperature. Selective oxidation of 2-alkylimidazolines in the presence of 2-arylimidazolines was achieved using this reagent system. 2-Imidazolines were also selectively converted to their corresponding imidazoles in the presence

  发现载于氧化铝上的高锰酸钾是在室温下于温和条件下将2-咪唑啉脱氢为咪唑的有效试剂体系。使用该试剂系统可以在2-芳基咪唑啉存在下选择性氧化2-烷基咪唑啉。在其他可氧化的官能团（例如硫化物，醚，醛，缩醛和THP醚）的存在下，还将2-咪唑啉选择性地转化为其相应的咪唑。这里描述的氧化过程容易进行，不需要严格的反应条件。