(1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl)imidazole | 470715-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl)imidazole
• 英文别名: 2-(1H-imidazol-1-ylcarbonyl)-1,2,3,4-tetrahydroisoquinoline；[3,4-dihydroisoquinolin-2(1H)-yl](1H-imidazol-1-yl)methanone；(3,4-dihydro-1H-isoquinolin-2-yl)(imidazol-1-yl)methanone；1H-Imidazol-1-yl 1,2,3,4-tetrahydroisoquinolin-2-yl ketone；3,4-dihydro-1H-isoquinolin-2-yl(imidazol-1-yl)methanone
• CAS: 470715-75-4
• 化学式: C₁₃H₁₃N₃O
• mdl: MFCD11782815
• 分子量: 227.266
• InChiKey: GWHYDXUKRKMJRI-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  418.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl)imidazole 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 生成 (3,4-dihydroisoquinolin-2(1H)-yl)(4-isopropylpiperazin-1-yl)methanone
  参考文献：
  名称：

  Ureas with histamine H3-antagonist receptor activity—A new scaffold discovered by lead-hopping from cinnamic acid amides

  摘要：

  A group of tri and tetrasubstituted urea derivatives have been found to be hH(3)-antagonists. The most potent compounds were found in the class of (piperazine-1-yl)-(piperidine-1-yl)-methanones which in addition showed negligible hERG inhibition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.093
• 作为产物：
  描述：

  四氢异喹啉 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 (1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl)imidazole
  参考文献：
  名称：

  叔氨基甲酰咪唑的不对称四取代脲：AlMe的活化3 †

  摘要：

  描述了一种由氨基甲酰咪唑合成不对称四取代脲的有效且通用的方法。通过同时使咪唑氮季铵化并用AlMe 3活化胺来实现转化。

  DOI：

  10.1039/c2ob25412c

文献信息

• Carbamoylimidazolium and thiocarbamoylimidazolium salts: novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides
  作者：Justyna A. Grzyb、Ming Shen、Chiaki Yoshina-Ishii、W. Chi、R.Stanley Brown、Robert A. Batey

  DOI：10.1016/j.tet.2005.05.056

  日期：2005.7

  Carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N,N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the ‘imidazolium’ effect. Kinetic studies on

  氨基甲酰咪唑鎓盐可作为有效的N，N-二取代的氨基甲酰化试剂。这些盐很容易通过用N，N依次处理仲胺来制备′-羰基二咪唑（CDI）和碘甲烷。由于“咪唑鎓”效应，因此氨基甲酰咪唑鎓盐是比中间氨基甲酰咪唑更有效的氨基甲酰转移试剂。对氨基甲酰咪唑盐和氨基甲酰咪唑鎓盐的碱促进水解的动力学研究表明，其加速百倍。该盐与胺，硫醇，酚/醇和羧酸以高收率反应，而无需对产物进行后续色谱纯化，分别生产尿素，硫代氨基甲酸酯，氨基甲酸酯和酰胺。还从仲胺和N，N′-硫代羰基二咪唑（TCDI）合成类似的硫代氨基甲酰咪唑鎓盐，然后用碘代甲烷甲基化。
• Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors
  作者：Liqiang Han、Yanzhao Wen、Ridong Li、Bo Xu、Zemei Ge、Xin Wang、Tieming Cheng、Jingrong Cui、Runtao Li

  DOI：10.1016/j.bmc.2017.05.049

  日期：2017.8

  and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors

  基于脯氨酸硼酸作为药效基团在激酶抑制剂中的应用以及我们先前的研究结果，以脯氨酸硼酸为战斗部，使用了两个系列的肽脯氨酸硼酸，二肽脯氨酸硼酸（I）和三肽设计并合成了脯氨酸硼酸（II）。首先评估所有合成的化合物对MGC803细胞的生物学活性，然后选择最佳的化合物II-7来测试其在六种人类肿瘤细胞系上的抗肿瘤谱以及对三个亚基的蛋白酶体抑制作用。结果表明，系列II具有比系列I更好的生物学活性。化合物II-7在细胞和蛋白酶体模型中不仅表现出优异的生物学活性（IC 50值为nM），而且亚单位选择性也好得多。因此，脯氨酸硼酸作为战斗部在蛋白酶体抑制剂的设计中是合理的。
• Unsymmetrical tetrasubstituted ureas from tertiary carbamoylimidazole: activation by AlMe3
  作者：A. Velavan、S. Sumathi、K. K. Balasubramanian

  DOI：10.1039/c2ob25412c

  日期：——

  An efficient and general method for the synthesis of unsymmetrical tetrasubstituted ureas from carbamoylimidazole is described. The conversion is achieved by the concurrent quarternization of the imidazole nitrogen and activation of amines with AlMe3.

  描述了一种由氨基甲酰咪唑合成不对称四取代脲的有效且通用的方法。通过同时使咪唑氮季铵化并用AlMe 3活化胺来实现转化。
• Unprecedented “In Water” Imidazole Carbonylation: Paradigm Shift for Preparation of Urea and Carbamate
  作者：Kamlesh J. Padiya、Sandip Gavade、Bhavana Kardile、Manojkumar Tiwari、Swapnil Bajare、Madhav Mane、Vivek Gaware、Shaji Varghese、Dipak Harel、Suresh Kurhade

  DOI：10.1021/ol301009d

  日期：2012.6.1

  The first "In Water" Imidazolecarbonylation of amine is described. A one pot reaction of carbonylimidazolide in water with a nucleophile provides an efficient and general method for the preparation of urea, carbamates and thiocarbamates. Use of an anhydrous solvent and an inert atmosphere could be avoided. Product precipitate out from the reaction mixture and can be obtained In high purity by filtration, resulting in a simple and scalable method.
• 1<i>H</i>-Imidazol-1-yl 1,2,3,4-tetrahydroisoquinolin-2-yl ketone
  作者：Justyna A. Grzyb、Alan J. Lough、Robert A. Batey

  DOI：10.1107/s0108270104019195

  日期：2004.10.15

  In the crystal structure of the title compound, C13H13N3O, the C - N-imidazole bond length of 1.431 (3) Angstrom is shorter than that observed [1.466 (6) Angstrom] in the corresponding carbamoylimidazolium salt 3-methyl-1-(1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl) imidazolium iodide. A comparision of these compounds is used to highlight the structural differences that occur as a result of the imidazolium effect. Weak C - H...O hydrogen bonds link molecules into extended tapes in the a direction.