5-乙烯基-1H-咪唑 | 3718-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-乙烯基-1H-咪唑
• 英文名称: 5-vinylimidazole
• 英文别名: 4-Vinylimidazol；5-vinyl-1H-imidazole；4-vinyl-1(3)H-imidazole；5-ethenyl-1H-imidazole
• CAS: 3718-04-5
• 化学式: C₅H₆N₂
• mdl: MFCD00061511
• 分子量: 94.116
• InChiKey: MHQZDNQHLGFBRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  5-乙烯基-1H-咪唑 在 硫酸氢铵 、 对叔丁基邻苯二酚 、 水 作用下， 以 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 5-乙烯基-1-甲基咪唑
  参考文献：
  名称：

  Imidazole Polymers Derived from Ionic Liquid 4-Vinylimidazolium Monomers: Their Synthesis and Thermal and Dielectric Properties

  摘要：

  The synthesis of 1-ethyl-3-methyl-4-vinylimidazolium triflate, its polymerization, and ion exchange to yield a family of 4-imidazolium polymers with a variety of anions are described. For comparative purposes, the synthesis, polymerization, and ion exchange of an analogous set of 1-vinylimidazolium polymers are also presented. The comparative thermal and dielectric characteristics of the 4-vinyl-and 1-vinylimidazolium salts were evaluated. The trends in the glass transition (T-g) characteristics of the various 4-vinylimidazolium and 1-vinylimidazolium polymers were similar; however, the glass transition temperatures of poly(4-vinylimidazolium) BF4- PF6-, AsF6-, and CF3SO3- salts were significantly higher than those of the corresponding poly(1-vinylimidazolium) salts. This difference and the increase in T-g in going from BF4- to AsF6- in the 4-vinylimidazolium series were attributed to enhanced intramolecular bridging between imidazolium moieties positioned 1,3 or 1,5 along the polymer chain. In the dielectric spectra of I-vinylimidazolium salts at temperatures in excess of 30 degrees C, one relaxation mode distinct from that for electrode polarization is observed. The single mode appears to correspond to the alpha-relaxation peak in poly(3-ethyl-1-vinylimidazolium salts) recently identified and attributed to ion-pair motion by Nakamura et al. In the 4-vinylimidazolium polymer spectra set, at temperatures in excess of 30 degrees C, two relaxation modes, distinct from that for electrode polarization, are apparent: the alpha peak also observed in the 1-vinylimidazolium polymer set and a new relaxation peak observed at lower frequency. The lower frequency relaxation peak is identified in this work as the alpha'-relaxation and is also associated with ion-pair motion. Assuming the relaxation processes to be Arrhenius in nature, the activation energy of the alpha-relaxation in poly(4-vinylimidazolium) BF4-, PF6-, CF3SO3-, TFSI-, and C2N3- salts ranged from 83 to 28 kJ/mol and appears to scale with the glass transition temperature.

  DOI：

  10.1021/ma300862t
• 作为产物：
  描述：

  1-tosyl-4-vinyl-1H-imidazole 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以85%的产率得到5-乙烯基-1H-咪唑
  参考文献：
  名称：

  通过量身定制和优化的氧化Heck交叉偶联功能实现咪唑骨架的功能化

  摘要：

  公开了芳族硼酸与乙烯基咪唑的一般和选择性Pd催化交叉偶联。与大多数交叉偶联反应不同，该方法在没有碱的情况下运行良好，避免了副产物的形成。氮基配体（特别是红霉素）的存在可大大提高反应性。该方法涉及MnO 2作为氧化Pd（0）→Pd（II）的氧化剂，它比以前文献中报道的要弱得多。这允许使用具有多个官能团的反应物。范围和限度研究涉及一系列24种硼酸，其中18种提供的TM产率在41–95％范围内。所公开的方法构成了在咪唑支架上进行氧化性Heck交叉偶联的第一种通用方法，该方法还可以与其他杂环一起选择。

  DOI：

  10.1002/adsc.202000909

文献信息

• [EN] 1,2,3,4-TETRAHYDROISOQUINOLINE COMPOUNDS AND COMPOSITIONS AS SELECTIVE ESTROGEN RECEPTOR ANTAGONISTS AND DEGRADERS<br/>[FR] COMPOSÉS ET COMPOSITIONS DE 1,2,3,4-TÉTRAHYDROISOQUINOLÉINE EN TANT QU'ANTAGONISTES ET AGENTS DE DÉGRADATION SÉLECTIFS DES RÉCEPTEURS DES ŒSTROGÈNES
  申请人：NOVARTIS AG

  公开号：WO2015092634A1

  公开（公告）日：2015-06-25

  The present invention relates to compounds of formula (I) in which n, R1, R2, R3, R4and R5 are as defined in the claims; capable of being both potent antagonists and degraders of estrogen receptors. Also described is a process for the preparation of compounds of the invention, and the invention further provides pharmaceutical preparations comprising such compounds and methods of using such compounds and compositions in the management of diseases or disorders associated with aberrant estrogen receptor activity.

  本发明涉及式(I)化合物，其中n、R1、R2、R3、R4和R5如权利要求所述；能够作为雌激素受体的强效拮抗剂和降解剂。还描述了制备本发明化合物的方法，并且本发明进一步提供了包含该化合物的药物制剂以及使用该化合物和组合物管理与异常雌激素受体活性相关疾病或失调的方法。
• Discovery of an Acrylic Acid Based Tetrahydroisoquinoline as an Orally Bioavailable Selective Estrogen Receptor Degrader for ERα+ Breast Cancer
  作者：Heather E. Burks、Tinya Abrams、Christina A. Kirby、Jason Baird、Alexander Fekete、Lawrence G. Hamann、Sunkyu Kim、Franco Lombardo、Alice Loo、Danuta Lubicka、Kaitlin Macchi、Donald P. McDonnell、Yuji Mishina、John D. Norris、Jill Nunez、Chitra Saran、Yingchuan Sun、Noel M. Thomsen、Chunrong Wang、Jianling Wang、Stefan Peukert

  DOI：10.1021/acs.jmedchem.6b01468

  日期：2017.4.13

  as a potent ERα antagonist and selective estrogen receptor degrader (SERD), exhibiting good oral bioavailability, antitumor efficacy, and SERD activity in vivo. We outline the discovery and chemical optimization of the THIQ scaffold leading to THIQ 40 and showcase the racemization of the scaffold, pharmacokinetic studies in preclinical species, and the in vivo efficacy of THIQ 40 in a MCF-7 human breast

  四氢异喹啉40已被确定为有效的ERα拮抗剂和选择性雌激素受体降解剂（SERD），在体内具有良好的口服生物利用度，抗肿瘤功效和SERD活性。我们概述了导致THIQ 40的THIQ支架的发现和化学优化，并展示了支架的消旋作用，临床前物种的药代动力学研究以及THIQ 40在MCF-7人乳腺癌异种移植模型中的体内功效。
• Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors
  作者：A. Keeley、P. Ábrányi-Balogh、G. M. Keserű

  DOI：10.1039/c8md00327k

  日期：——

  A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads.

  通过半胱氨酸反应性和水稳定性测试，对亲电性小杂环片段库进行了表征，结果表明它们有潜力作为共价战斗头。
• [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）。
• Asymmetric Organocatalytic Synthesis of Bisindoles - Scope and Derivatizations
  作者：Christina Retich、Stefan Bräse

  DOI：10.1002/ejoc.201701502

  日期：2018.1.10

  library of various novel biologically active bisindoles with different substitution patterns was synthesized. Electro‐withdrawing groups on the starting material led to the formation of Povarov‐type structures. Furthermore we could successfully demonstrate that consecutive reactions like cross couplings, reductions or even click reactions on bisindoles are feasible.

  合成了具有不同取代模式的各种新型生物活性双吲哚的文库。起始材料上的吸电基团导致形成Povarov型结构。此外，我们可以成功地证明在双吲哚上进行诸如交叉偶联，还原甚至点击反应之类的连续反应是可行的。