2-苯基-1H-咪唑-4,5-二甲酸二甲酯 | 52122-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-1H-咪唑-4,5-二甲酸二甲酯
• 中文别名: 4-噻唑羧酸,2-(3-乙基苯基)-,乙基酯
• 英文名称: dimethyl 2-phenyl-1H-imidazole-4,5-dicarboxylate
• 英文别名: dimethyl 2-phenylimidazole-4,5-dicarboxylate；2-phenyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester
• CAS: 52122-98-2
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: HHXCJFMOJFOZCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-苯基-1H-咪唑-4,5-二甲酸二甲酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 88.0h， 生成 [1-methyl-5-(methylcarbamoyloxymethyl)-2-phenylimidazol-4-yl]methyl N-methylcarbamate
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023
• 作为产物：
  描述：

  丁炔二酸二甲酯 在 盐酸 作用下， 以 Petroleum ether 为溶剂， 反应 48.0h， 生成 2-苯基-1H-咪唑-4,5-二甲酸二甲酯
  参考文献：
  名称：

  Casey, Michael; Moody, Christopher J.; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1985, p. 741 - 746

  摘要：

  DOI：

文献信息

• [EN] PHENYL-ANILINE SUBSTITUTED BICYCLIC COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSES BICYCLIQUES A SUBSTITUTION PHENYL-ANILINE UTILISES COMME INHIBITEUR DE LA KINASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005042537A1

  公开（公告）日：2005-05-12

  Compounds having the formula (I), and pharmaceutically acceptable salts, prodrugs, and solvates thereof, are useful as kinase inhibitors, wherein R, R1 , R2, R5, R6a, R6b, J, K, X and Z are as described in the specification.

  具有化学式（I）的化合物，以及其药学上可接受的盐、前药和溶剂化合物，可用作激酶抑制剂，其中R、R1、R2、R5、R6a、R6b、J、K、X和Z如规范中所述。
• Design and synthesis of optically active 2-phenylimidazolecarboxamides featuring amino acid motive
  作者：Roman Sivek、Oldřich Pytela、Filip Bureš

  DOI：10.1002/jhet.5570450611

  日期：2008.11

  sixteen new, optically active carboxamides 1-3 have been synthesized. These compounds based on the 2-phenylimidazole and featuring amino acid residues are linked on the 4-position by an amidic bond. Two general methods were used for their construction. Whereas the first method employs acylchlorides as a reactive species, the second one involves a condensation of mixed anhydrides with the amino acid counterparts

  总共合成了十六种新的旋光羧酰胺1-3。这些基于2-苯基咪唑并具有氨基酸残基的化合物通过酰胺键在4-位连接。使用两种通用方法进行构造。第一种方法采用酰氯作为反应性物质，而第二种方法则涉及混合酸酐与氨基酸对应物的缩合反应。实际上，第二种方法被证明比第一种方法更有效。初步将羧酰胺1-3作为N螯合配体进行了测试，并应用于亨利或阿尔多反应中，收率不佳或对映体过量。
• Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp³)–H and C(sp²)–H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds
  作者：Srilaxmi M. Patel、Ermiya Prasad P.、Manickam Bakthadoss、Duddu S. Sharada

  DOI：10.1021/acs.orglett.0c03269

  日期：2021.1.15

  imidazoles and privileged dihydroisoquinoline-based imidazole derivatives via C(sp3)–H and C(sp2)–H bond functionalization. A sustainable, convenient, metal-free azidation/C–H aminative cyclization approach in the absence of stoichiometric oxidants is presented. This protocol involves a rare photoinduced iminyl radical as a key intermediate for the “N” insertion.

  在这里，我们证明了可见光介导的无金属有机染料催化的脱氢N插入通过C（sp 3）–H和C（sp 2）–H导致高度取代的咪唑和特权的基于二氢异喹啉的咪唑衍生物键功能化。提出了一种在没有化学计量氧化剂的情况下可持续，方便，无金属的叠氮化/ CH胺化环化方法。该协议涉及罕见的光诱导亚胺基，作为“ N”插入的关键中间体。
• in vitro inhibition of the measles virus by novel ring-expanded (‘fat’) nucleoside analogues containing the imidazo[4,5-e]diazepine ring system
  作者：Ning Zhang、Huan-Ming Chen、Ramesh Sood、Kishna Kalicharran、Ali I Fattom、Robert B Naso、Dale L Barnard、Robert W Sidwell、Ramachandra S Hosmane

  DOI：10.1016/s0960-894x(02)00762-x

  日期：2002.12

  activity in African green monkey kidney cells (CV-1), employing ribavirin as the control standard. While the parent compound 1 itself failed to show any significant antiviral activity against MV, its analogues containing hydrophobic substituents at the 2-position (2) or the 6-position (4) showed promising antiviral activity at submicromolar or micromolar concentration levels with no apparent toxicity to

  据报道，含有标题杂环系统的一类环膨胀（“脂肪”）核苷类似物（1-4）的合成和体外抗麻疹病毒（anti-MV）活性。通过适当取代的咪唑-1-核糖苷的4，5-二羧酸酯与适当取代的胍衍生物的碱催化缩合来合成目标化合物。以利巴韦林为对照标准，筛选化合物在非洲绿猴肾细胞（CV-1）中的抗MV活性。虽然母体化合物1本身未显示出对MV的任何重要抗病毒活性，其在2位（2）或6位（4）处含有疏水取代基的类似物在亚微摩尔或微摩尔浓度水平下显示出有希望的抗病毒活性，对宿主细胞系无明显毒性。两种化合物均显示出比对照药物利巴韦林更高的抗MV活性。
• The photochemistry of α-Azidocinnamates - a reinvestigation
  作者：Otto Meth-Cohn、Nicola J.R Williams、Angus MacKinnon、Judith A.K Howard

  DOI：10.1016/s0040-4020(98)00537-7

  日期：1998.8

  efficient manner by photolysis using quartz equipment.1 We find that use of pyrex filters or ketone sensitisation instead of quartz leads to high yields of the presumed intermediate diastereomeric pair of aziridinoimidazoline dimers, as does brief irradiation in quartz. These dimers have been characterised by spectral and crystallographic methods, and shown to oxidise with DDQ to give imidazoledicarboxylic

  在其他地方已经报道了α-Azicdocinnamates通过使用石英设备进行光解以逐步有效的方式生成三聚体的一种非对映异构体。1我们发现，使用派热克斯滤光片或酮敏化代替石英会导致假定的中间非对映异构对叠氮基咪唑啉二聚体的高收率，就像在石英中短暂照射一样。这些二聚体已通过光谱和晶体学方法表征，并显示可与DDQ氧化生成咪唑二羧酸酯，而碱对两种二聚体非对映体的作用均导致一个重排的二聚体1，2-二氢嘧啶。令人惊讶地，只有两种非对映异构体二聚体的混合物才使三聚体进一步光解。