2-(2-chlorophenyl)methylimidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-chlorophenyl)methylimidazole
• 英文别名: 2-chlorobenzylimidazole；2-(2-chlorobenzyl)-1H-imidazole；2-[(2-chlorophenyl)methyl]-1H-imidazole
• 化学式: C₁₀H₉ClN₂
• 分子量: 192.648
• InChiKey: CGYRZILXCROPRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)methylimidazole 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-(1-(2-chlorobenzyl)-1H-imidazolium-3-yl)-3-methylindolate
  参考文献：
  名称：

  Betaine–Carbene Interconversions. From N-Ylides to Zwitterionic N-Heterocyclic Carbene–Borane Adducts

  摘要：

  In the presence of NBS 3-methylindole reacted with various imidazoles to give the (indol-2-yl)imidazolium salts 21a-f, which were converted in aqueous solution into the 2-(imidazolium-3-yl)-3-methylindolates 22a-f by base. These conjugated ylides-which represent a subclass of mesomeric betaines-are the exclusively detectable form in the NMR spectra taken in DMSO-d(6). A DFT calculation revealed that the betaine 22a is -9.3 kJ/mol more stable than the tautomeric N-heterocyclic carbene 23a and that the energy for the betaine-carbene interconversion is Delta G(double dagger) = 66.4 kJ/mol. The N-heterocyclic carbenes (3-methyl-indol-2-yl)imidazol-2-ylidenes, however, can be trapped by sulfur, triethylborane, and triphenylborane. Whereas the first trapping reaction yielded the expected imidazolethiones, the borates gave the first representatives of new zwitterionic borane adducts, imidazo[2',1':3,4][1,4,2]diazaborolo[1,5-a]indolium-11-ides 26a-h. We performed DFT calculations on the structures of mesomeric betaine 22a, the carbene 23a, and the mechanisms of the borane adduct formation to 26a-h, NMR spectroscopic investigations including N-15, Li-7, and B-11 NMR spectroscopy, and an X-ray single-crystal analysis of one of the borane adducts.

  DOI：

  10.1021/jo302479p
• 作为产物：
  描述：

  2-(2-chlorophenylmethyl)-2-imidazoline 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以68%的产率得到2-(2-chlorophenyl)methylimidazole
  参考文献：
  名称：

  A novel synthetic method for 2-arylmethyl substituted imidazolines and imidazoles from 2-aryl-1,1-dibromoethenes

  摘要：

  Various 2-arylmethylimidazolines were prepared by treating readily available 2-aryl-1, 1-dibromoethenes with ethylenediamine under mild conditions and further converted into the corresponding imidazoles smoothly with Swern oxidation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.035

文献信息

• [EN] TRIAZINE COMPOUNDS AS KINASE INHIBITORS<br/>[FR] COMPOSÉS DE TRIAZINE COMME INHIBITEURS DE LA KINASE
  申请人：S BIO PTE LTD

  公开号：WO2009093981A1

  公开（公告）日：2009-07-30

  The present invention relates to triazine compounds that are useful as kinase inhibitors. More particularly, the present invention relates to morpholino substituted triazines, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases or PI3 kinases. The compounds are of the formula (I).

  本发明涉及作为激酶抑制剂有用的三嗪化合物。更具体地说，本发明涉及吗啡啶取代的三嗪，其制备方法，含有这些化合物的药物组合物以及这些化合物在治疗增生性疾病中的用途。这些化合物可能作为药物用于治疗多种增生性疾病，包括肿瘤和癌症以及与mTOR激酶或PI3激酶相关的其他疾病或病况。这些化合物的结构如下（I）。
• Substituted imidazole and imidazoline derivatives and their preparation and use
  申请人：Farmos-Yhtyma Oy

  公开号：EP0064820A1

  公开（公告）日：1982-11-17

  The invention provides novel compounds of the formu- ' la: wherein each of R1, R2 and R3, which can be the same or different, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy or nitro; R4 and R5, which can be the same or different, are hydrogen, an alkyl radical of 1 to 7 carbon atoms, hydroxymethyl or R6 is hydrogen, an alkyl radical of 1 to 7 carbon atoms or R7 and R8 are hydrogen, chloro or methyl; X is-CH=CH- or CHR9; Rg is hydrogen or hydroxy; n is 0-7 and m is 0-6; and their non-toxic pharmaceutically acceptable acid addition salts and mixtures thereof. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions comprising at least one of the compounds and their salts. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as antihypertensives and also as antithrombotic and antimycotic agents.

  本发明提供了如下形式的新型化合物： 其中 R1、R2 和 R3（可以相同或不同）分别为氢、氯、溴、氟、甲基、乙基、甲氧基、氨基、羟基或硝基；R4 和 R5（可以相同或不同）分别为氢、1 至 7 个碳原子的烷基、羟甲基或硝基。 R6 是氢、1 至 7 个碳原子的烷基或 R7和R8是氢、氯或甲基；X是-CH＝CH-或CHR9；Rg是氢或羟基；n是0-7，m是0-6；以及它们的无毒药学上可接受的酸加成盐及其混合物。本文描述了这些化合物的制备过程，以及包含至少一种化合物及其盐类的新型药物组合物。这些化合物及其无毒盐具有重要的药理活性，可用于哺乳动物的治疗，特别是作为抗高血压药以及抗血栓和抗霉菌药。
• Imidazolyl-alkenoic acids
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0403158A2

  公开（公告）日：1990-12-19

  Angiotensin II receptor antagonists having the formula: which are useful in requlating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mamnals.

  式的血管紧张素 II 受体拮抗剂： 可用于调节高血压和治疗充血性心力衰竭、肾功能衰竭和青光眼的拮抗剂，包括这些拮抗剂的药物组合物，以及使用这些化合物在动物体内产生血管紧张素 II 受体拮抗作用的方法。
• Substituted 5-((tetrazolyl)alkenyl)-imidazoles
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0425211A1

  公开（公告）日：1991-05-02

  Angiotensin II receptor antagonists having the formula: which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.

  式的血管紧张素 II 受体拮抗剂： 用于调节高血压和治疗充血性心力衰竭、肾功能衰竭和青光眼的血管紧张素 II 受体拮抗剂，包括这些拮抗剂的药物组合物，以及使用这些化合物在哺乳动物体内产生血管紧张素 II 受体拮抗作用的方法。
• EP0563238A4
  申请人：——

  公开号：EP0563238A4

  公开（公告）日：1994-08-24