5-[(三甲基硅烷)乙炔基])-1-甲基咪唑 | 480439-45-0

• 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-[(三甲基硅烷)乙炔基])-1-甲基咪唑
• 中文别名: 5-[(三甲基硅基)乙炔基])-1-甲基咪唑
• 英文名称: 5-(trimethylsilyl)ethynyl-1-methylimidazole
• 英文别名: 1-methyl-5-((trimethylsilyl)ethynyl)-1H-imidazole；trimethyl-[2-(3-methylimidazol-4-yl)ethynyl]silane
• CAS: 480439-45-0
• 化学式: C₉H₁₄N₂Si
• mdl: MFCD04039965
• 分子量: 178.309
• InChiKey: ZNCKMUMVQDCZBO-UHFFFAOYSA-N

物化性质

• 熔点：
  55-59 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36/37/39
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-[(三甲基硅烷)乙炔基])-1-甲基咪唑 在 正丁基锂 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 C₁₁H₁₇N₃OSi
  参考文献：
  名称：

  Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR–ABL including the T315I gatekeeper mutant

  摘要：

  Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.060
• 作为产物：
  描述：

  5-溴-1-甲基-1H-咪唑 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-[(三甲基硅烷)乙炔基])-1-甲基咪唑
  参考文献：
  名称：

  Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR–ABL including the T315I gatekeeper mutant

  摘要：

  Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.060

文献信息

• Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions
  作者：Socrates B. Munoz、Alexandra N. Aloia、Alexander K. Moore、Attila Papp、Thomas Mathew、Santos Fustero、George A. Olah、G. K. Surya Prakash

  DOI：10.1039/c5ob02187a

  日期：——

  method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl)alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently “unmasked”

  已经开发了一种在水相转移条件下合成3-亚甲基-异吲哚啉-1-酮4的简便方法。从2-碘联苯甲酰胺1和（甲硅烷基）炔烃开始，在n -Bu 4 NBr（TBAB）存在下，使用廉价的CuCl / PPh 3催化剂体系，可以高收率和短反应时间（30分钟）获得产物。作为相转移剂。在反应条件下，原位甲硅烷基化可方便地对“末端炔烃”进行“掩蔽” 。还发现具有杂环部分的炔烃是合适的底物。此外，从2-碘苯甲酰胺1开始的一锅法在Pd / Cu催化下，芳基卤化物（溴化物或碘化物）和三甲基甲硅烷基乙炔（TMSA）作为方便的乙炔替代物也是可行的。
• Synthesis and structural characterization of alkyne-functionalized N-heterocyclic carbene complexes of ruthenium, palladium and rhodium
  作者：Edith Chardon、Georges Dahm、Gilles Guichard、Stéphane Bellemin-Laponnaz

  DOI：10.1016/j.ica.2017.07.034

  日期：2017.10

  Abstract A series of novel ruthenium(II), palladium(II) and rhodium(I) complexes bearing N-heterocyclic carbene ligand functionalized by an alkyne-protected functional group ( C C SiMe3) were synthesized by transmetalation from the silver-NHC intermediate or by deprotonation of the azolium salt using an external base. The complexes were fully characterized and X-ray diffraction was used for the structure

  摘要通过银-NHC中间体或通过NHC银的过渡金属化合成了一系列带有由炔烃保护的官能团（CC SiMe3）官能化的N-杂环卡宾配体的新型钌（II），钯（II）和铑（I）配合物。使用外部碱使偶氮盐去质子化。对该配合物进行了充分表征，并使用X射线衍射确定了结构。通过合成羰基铑配合物评估了NHC配体的给体性质。已经研究了官能团的反应性：炔在钌和铑物种上的脱保护得到不稳定的产物，而钯化合物的脱保护是定量的。
• Synthesis, Structure and Antitumoural Activity of Triazole‐Functionalised NHC–Metal Complexes
  作者：Marco Monticelli、Stéphane Bellemin‐Laponnaz、Cristina Tubaro、Marzio Rancan

  DOI：10.1002/ejic.201700142

  日期：2017.5.10

  Silver(I), gold(I), copper(I) and ruthenium(II) N-heterocyclic carbene (NHC) complexes have been synthesised and their cytotoxic activities towards various cancer cell lines have been evaluated. The N-heterocyclic carbene ligand has been functionalised with a 1,2,3-triazole moiety tethered in the backbone of the ligand. The molecular structure of the silver(I) and gold(I) complexes has been solved

  已经合成了银 (I)、金 (I)、铜 (I) 和钌 (II) N-杂环卡宾 (NHC) 复合物，并评估了它们对各种癌细胞系的细胞毒活性。N-杂环卡宾配体已经用连接在配体骨架中的1,2,3-三唑部分进行了功能化。银 (I) 和金 (I) 配合物的分子结构已通过 X 射线衍射分析解决。AgI、AuI 和 RuII 复合物在水性条件下表现出良好的稳定性，并显示出与类似的未官能化复合物相当或略优的细胞毒活性。
• Synthesis of <i>N</i>-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of <i>N</i>-CF₃ Carbamoyl Fluorides
  作者：Christian D.-T. Nielsen、Filip G. Zivkovic、Franziska Schoenebeck

  DOI：10.1021/jacs.1c07780

  日期：2021.8.25

  N-trifluoromethyl alkynamides. Our strategy relies on a mild and operationally simple Ni-catalyzed coupling of N-CF3 carbamoyl fluorides with alkynyl silanes. The synthesized N-CF3 alkynamides proved to be highly robust and readily functioned as a platform to unlock access to valuable derivatives, such as N-CF3 decorated alkenyl amides, oxindoles, or quinolones, all of which were inaccessible to date.

  与无处不在的基序相关的化学空间的扩展是释放新特性和功能的关键。在这种情况下，广泛存在于众多药物和材料中的炔酰胺代表了一种尚未开发的资源。我们在此报告了对N-三氟甲基炔酰胺的首次合成途径。我们的策略依赖于N -CF 3氨基甲酰氟与炔基硅烷的温和且操作简单的 Ni 催化偶联。合成的N -CF 3炔酰胺被证明是高度稳健的，并且很容易作为一个平台来解锁对有价值的衍生物的访问，例如N -CF 3 修饰的链烯基酰胺、羟吲哚或喹诺酮类，所有这些迄今为止都无法获得。
• Lewis Base-catalyzed Alkynylation of Carbonyl Compounds with Trimethylsilylacetylenes
  作者：Takayuki Kitazawa、Tomofumi Minowa、Teruaki Mukaiyama

  DOI：10.1246/cl.2006.1002

  日期：2006.9

  Alkynylation of carbonyl compounds with trimethylsilylacetylenes in the presence of a catalytic amount of Lewis bases such as acetate or phenoxide anion is described. The alkynylation proceeded under mild conditions and afforded the corresponding propargyl alcohols in good to excellent yields.

  描述了一种在催化量路易斯碱（如醋酸根或苯氧根）存在下，使用三甲基硅基乙炔与羰基化合物进行炔基化的反应。该炔基化反应在温和条件下进行，获得了相应的丙炔醇，产率良好到优秀。