1-氯-4-三甲基锡-3-丁炔-2-酮 | 18245-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-氯-4-三甲基锡-3-丁炔-2-酮
• 中文别名: 1-氯-4-(三甲基硅基)-3-丁炔-2-酮
• 英文名称: 1-chloro-4-(trimethylsilyl)-3-butyne-2-one
• 英文别名: 1-chloro-4-(trimethylsilyl)-3-butyn-2-one；1-chloro-4-(trimethylsilyl)but-3-yn-2-one；4-Chloro-1-(trimethylsilyl)-1-butyn-3-one；1-chloro-4-trimethylsilyl-3-butyn-2-one；1-chloro-4-trimethylsilylbut-3-yn-2-one；4-trimethylsilyl-1-chloro-3-butyn-2-one
• CAS: 18245-82-4
• 化学式: C₇H₁₁ClOSi
• mdl: MFCD01862797
• 分子量: 174.702
• InChiKey: YNHLTRNOGXIHRW-UHFFFAOYSA-N

物化性质

• 沸点：
  187℃
• 密度：
  1.017
• 闪点：
  70℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  1-氯-4-三甲基锡-3-丁炔-2-酮 在 horse liver alcohol dehydrogenase 、 triethanolamine - HCl buffer 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 乙醇 为溶剂， 生成 (R)-1-Chloro-4-trimethylsilanyl-but-3-yn-2-ol
  参考文献：
  名称：

  Highly Enantioselective Preparation of Multifunctionalized Propargylic Building Blocks

  摘要：

  DOI：

  10.1002/1521-3773(20020215)41:4<634::aid-anie634>3.0.co;2-u
• 作为产物：
  描述：

  氯乙酰氯 、 二(三甲基甲硅烷基)乙炔 在 zeolite H-beta 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到1-氯-4-三甲基锡-3-丁炔-2-酮
  参考文献：
  名称：

  沸石催化导致噻唑环的构建：4-炔基取代的噻唑的改进合成

  摘要：

  H-β沸石促进α-氯代乙酰氯与1,2-双-三甲基甲硅烷基乙炔的反应，生成1-氯-4-（三甲基甲硅烷基）but-3-yn-2-one，经硫代乙酰胺处理后得到2 -甲基-4-[（三甲基甲硅烷基）乙炔基]噻唑。另一方面，1-脯氨酸在K 2 CO 3水溶液存在下，在Pd-Cu催化下促进了2-甲基-4-[（三甲基甲硅烷基）乙炔基]噻唑与（杂）芳基卤化物的偶联反应（改良的Sonogashira反应）。提供了一种用于合成相应的4-炔基取代的噻唑衍生物的改进方法。

  DOI：

  10.1016/j.tetlet.2012.05.062

文献信息

• Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications
  作者：Sean Preshlock、Samuel Calderwood、Stefan Verhoog、Matthew Tredwell、Mickael Huiban、Antje Hienzsch、Stefan Gruber、Thomas C. Wilson、Nicholas J. Taylor、Thomas Cailly、Michael Schedler、Thomas Lee Collier、Jan Passchier、René Smits、Jan Mollitor、Alexander Hoepping、Marco Mueller、Christophe Genicot、Joël Mercier、Véronique Gouverneur

  DOI：10.1039/c6cc03295h

  日期：——

  Eight clinically relevant radiotracers were isolated applying a Cu-mediated non-carrier added nucleophilic ¹⁸F-fluorination of arylboronic ester precursors.

  使用铜介导的非载体添加亲核性¹⁸F-氟化技术，从芳基硼酸酯前体中分离出了八种临床相关的放射性示踪剂。
• Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes
  作者：Pavel K Mykhailiuk

  DOI：10.3762/bjoc.11.3

  日期：——

  A one-pot reaction between C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes gives C₂F₅-substituted pyrazoles in excellent yields. The transformation smoothly proceeds in dichloromethane/water, tolerates the presence of air, and requires no purification of products by column chromatography. Mechanistically, C₂F₅CH₂NH₂·HCl and NaNO₂ react first in water to generate C₂F₅CHN₂, that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane.

  一种涉及C₂F₅CH₂NH₂·HCl、NaNO₂和缺电子炔烃的一锅反应，以优异的产率得到C₂F₅-取代的吡唑。该转化在二氯甲烷/水体系中顺利进行，耐受空气存在，且无需通过柱色谱法纯化产物。机理上，C₂F₅CH₂NH₂·HCl和NaNO₂首先在水相中反应生成C₂F₅CHN₂，然后与二氯甲烷中的缺电子炔烃进行[3 + 2]环加成反应。
• Convergent Synthesis of the Quinolone Substructure of BILN 2061 via Carbonylative Sonogashira Coupling/Cyclization
  作者：Nizar Haddad、Jonathan Tan、Vittorio Farina

  DOI：10.1021/jo060556q

  日期：2006.6.1

  A convergent synthesis of quinolone 2 (key substructure of the protease inhibitor BILN 2061) was developed via palladium-catalyzed carbonylation of 2-iodo-5-methoxyaniline (4) with thiazolylacetylene 5.

  通过钯催化的2-碘-5-甲氧基苯胺（4）与噻唑基乙炔5的羰基化反应，开发了喹诺酮2的聚合合成（蛋白酶抑制剂BILN 2061的关键亚结构）。
• Birkofer,L. et al., Chemische Berichte, 1963, vol. 96, p. 3280 - 3288
  作者：Birkofer,L. et al.

  DOI：——

  日期：——
• Insights into the interaction of negative allosteric modulators with the metabotropic glutamate receptor 5: Discovery and computational modeling of a new series of ligands with nanomolar affinity
  作者：Andrew Anighoro、Davide Graziani、Ilaria Bettinelli、Antonio Cilia、Carlo De Toma、Matteo Longhi、Fabio Mangiarotti、Sergio Menegon、Lorenza Pirona、Elena Poggesi、Carlo Riva、Giulio Rastelli

  DOI：10.1016/j.bmc.2015.05.008

  日期：2015.7

  Metabotropic glutamate receptor 5 (mGlu(5)) is a biological target implicated in major neurological and psychiatric disorders. In the present study, we have investigated structural determinants of the interaction of negative allosteric modulators (NAMs) with the seven-transmembrane (7TM) domain of mGlu(5). A homology model of the 7TM receptor domain built on the crystal structure of the mGlu(1) template was obtained, and the binding modes of known NAMs, namely MPEP and fenobam, were investigated by docking and molecular dynamics simulations. The results were validated by comparison with mutagenesis data available in the literature for these two ligands, and subsequently corroborated by the recently described mGlu(5) crystal structure. Moreover, a new series of NAMs was synthesized and tested, providing compounds with nanomolar affinity. Several structural modifications were sequentially introduced with the aim of identifying structural features important for receptor binding. The synthesized NAMs were docked in the validated homology model and binding modes were used to interpret and discuss structure-activity relationships within this new series of compounds. Finally, the models of the interaction of NAMs with mGlu(5) were extended to include important non-aryl alkyne mGlu(5) NAMs taken from the literature. Overall, the results provide useful insights into the molecular interaction of negative allosteric modulators with mGlu(5) and may facilitate the design of new modulators for this class of receptors. (C) 2015 Elsevier Ltd. All rights reserved.