2-乙烯基-1-甲基咪唑 | 16975-71-6

• 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-乙烯基-1-甲基咪唑
• 英文名称: 1-methyl-2-vinyl-1H-imidazole
• 英文别名: 2-ethenyl-1-methylimidazole
• CAS: 16975-71-6
• 化学式: C₆H₈N₂
• 分子量: 108.143
• InChiKey: PZBASOPBSCAZSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-乙烯基-1-甲基咪唑 在 sodium tetrahydroborate 、 N,N'-双(亚水杨基)乙二胺 、 manganese(ll) chloride 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 30.0h， 生成 2-(1-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)ethyl)-1,3-dimethyl-1H-imidazol-3-ium 4-methylbenzenesulfonate
  参考文献：
  名称：

  Chemical modifications of imidazole-containing alkoxyamines increase C–ON bond homolysis rate: Effects on their cytotoxic properties in glioblastoma cells

  摘要：

  Previously, we described alkoxyamines bearing a pyridine ring as new pro-drugs with low molecular weights and theranostic activity. Upon chemical stimulus, alkoxyamines undergo homolysis and release free radicals, which can, reportedly, enhance magnetic resonance imaging and trigger cancer cell death. In the present study, we describe the synthesis and the anti-cancer activity of sixteen novel alkoxyamines that contain an imidazole ring. Activation of the homolysis was conducted by protonation and/or methylation. These new molecules displayed cytotoxic activities towards human glioblastoma cell lines, including the U251-MG cells that are highly resistant to the conventional chemotherapeutic agent Temozolomide. We further showed that the biological activities of the alkoxyamines were not only related to their half-life times of homolysis. We lastly identified the alkoxyamine ( RS/SR)-4a, with both a high antitumour activity and favourable logD(7.4) and pK(a) values, which make it a robust candidate for blood-brain barrier penetrating therapeutics against brain neoplasia.

  DOI：

  10.1016/j.bmc.2019.03.029
• 作为产物：
  描述：

  2-(1-甲基-1H-咪唑基-2-基)乙醇 在 氢氧化钾 作用下， 生成 2-乙烯基-1-甲基咪唑
  参考文献：
  名称：

  2-Vinylimidazole and 1-Methyl-2-vinylimidazole

  摘要：

  DOI：

  10.1021/ja01110a029

文献信息

• Hydrazines and Azides via the Metal-Catalyzed Hydrohydrazination and Hydroazidation of Olefins
  作者：Jérôme Waser、Boris Gaspar、Hisanori Nambu、Erick M. Carreira

  DOI：10.1021/ja062355+

  日期：2006.9.1

  which the H and the N atoms come from two different reagents, a silane and an oxidizing nitrogen source (azodicarboxylate or sulfonyl azide). The hydrohydrazination reaction using di-tert-butyl azodicarboxylate is characterized by its ease of use, large functional group tolerance, and broad scope, including mono-, di-, tri-, and tetrasubstituted olefins. Key to the development of the hydroazidation

  报道了 Co 和 Mn 催化的烯烃加氢肼和加氢叠氮化反应的发现、研究和实施。这些反应等效于 CC 双键与受保护的肼或偶氮酸的直接加氢胺化，但基于不同的概念，其中 H 和 N 原子来自两种不同的试剂，硅烷和氧化性氮源（偶氮二羧酸或磺酰叠氮化物） ）。使用偶氮二羧酸二叔丁酯的加氢肼反应具有使用方便、官能团耐受性大、适用范围广的特点，包括单、二、三和四取代烯烃。氢叠氮化反应发展的关键是使用磺酰叠氮化物作为氮源和叔丁基过氧化氢的活化作用。发现该反应对于单、二和三取代烯烃的官能化是有效的，并且只有少数官能团是不能容忍的。获得的烷基叠氮化物是通用中间体，可以在不分离叠氮化物的情况下转化为游离胺或三唑。初步的机理研究表明，烯烃的氢化钴是限速的，然后是胺化反应。不能排除并可能涉及自由基中间体。然后进行胺化反应。不能排除并可能涉及自由基中间体。然后进行胺化反应。不能排除并可能涉及自由基中间体。
• New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles
  作者：Jennifer Kerhervé、Candice Botuha、Joëlle Dubois

  DOI：10.1039/b902601k

  日期：——

  cross-coupling reactions of 2-iodoimidazole have been studied to synthesize imidazole-containing protein farnesyltransferase inhibitors. The Suzuki coupling reaction proved to be very efficient to introduce functionalized alkyl chains at the 2-position of the imidazole ring and a new synthesis of the required alkenylboronates was realised by a reaction of cross metathesis. Asymmetric synthesis of allyl succinic

  钯 的催化交叉偶联反应 2-碘咪唑 已经研究合成 咪唑含蛋白质法呢基转移酶抑制剂。铃木偶联反应被证明非常有效地在咪唑环的2位引入官能化的烷基链，并且通过交叉复分解反应实现了所需烯基硼酸酯的新合成。烯丙基琥珀酸衍生物的不对称合成使我们能够通过Suzuki偶联合成手性蛋白法呢基转移酶抑制剂，并确定我们抑制剂的立体化学对酶活性的影响。
• [EN] PERSONAL CARE COMPOSITIONS CONTAINING CERTAIN CYCLIC SILOXANES<br/>[FR] COMPOSITIONS DE SOINS PERSONNELS CONTENANT CERTAINS SILOXANES CYCLIQUES
  申请人：DOW CORNING

  公开号：WO2011066359A1

  公开（公告）日：2011-06-03

  Personal care compositions containing certain cyclic siloxanes are disclosed. The cyclic siloxanes are prepared by reacting a chloro endblocked polydimethylsiloxane with a diol functional compound containing at least 2 carbon atoms.

  本发明涉及含有特定环状硅氧烷的个人护理组合物。所述环状硅氧烷是通过将氯端封闭的聚二甲基硅氧烷与至少含有2个碳原子的二元醇官能化合物反应制备而成。
• Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity
  作者：Priyanka Bajaj、Gopeekrishnan Sreenilayam、Vikas Tyagi、Rudi Fasan

  DOI：10.1002/anie.201608680

  日期：2016.12.23

  In combination with whole‐cell biotransformations, these stereocomplementary biocatalysts enabled the multigram synthesis of the chiral cyclopropane core of four drugs (Tranylcypromine, Tasimelteon, Ticagrelor, and a TRPV1 inhibitor) in high yield and with excellent diastereo‐ and enantioselectivity (98–99.9% de; 96–99.9% ee). These biocatalytic strategies outperform currently available methods to produce

  工程化血红素蛋白最近已成为促进不对称环丙烷化的有前景的系统，但在这些反应中具有可预测、互补立体选择性的变体仍然难以捉摸。在这项研究中，实施了一种合理驱动的策略，并将其应用于工程肌红蛋白变体，这些变体能够提供具有高反式(1R,2R)选择性和催化活性的1-羧基-2-芳基-环丙烷。这些环丙烷化生物催化剂的立体选择性补充了此处和之前开发的反式（1S，2S）选择性变体的立体选择性。与全细胞生物转化相结合，这些立体互补生物催化剂能够以高产率合成四种药物（反苯环丙明、他司美琼、替格瑞洛和 TRPV1 抑制剂）的手性环丙烷核心，并具有优异的非对映和对映选择性（98-99.9%） de；96–99.9% ee）。这些生物催化策略优于目前可用的生产这些药物的方法。
• IONIC POLYMERS AND USE THEREOF IN BIOMASS PROCESSING
  申请人：EMBION TECHNOLOGIES SA

  公开号：US20200246785A1

  公开（公告）日：2020-08-06

  The invention provides ionic polymers (IP) consisting of anions and a polymeric backbone containing cations. The invention also provides the ionic polymers incorporated in membranes or attached to solid supports and use of the ionic polymers in processing of biomass.

  该发明提供了由阴离子和含有阳离子的聚合骨架组成的离子聚合物（IP）。该发明还提供了将离子聚合物并入膜中或附着在固体支撑物上，并将离子聚合物用于生物质加工的方法。