2-(4-溴-2-甲基苯基)乙炔基三甲基硅烷 | 221292-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-溴-2-甲基苯基)乙炔基三甲基硅烷
• 英文名称: 2-(trimethylsilyl)ethynyl-5-bromotoluene
• 英文别名: ((4-bromo-2-methylphenyl)ethynyl)trimethylsilane；5-bromo-2-(trimethylsilylethynyl)toluene；2-(4-Bromo-2-methylphenyl)ethynyl-trimethylsilane
• CAS: 221292-47-3
• 化学式: C₁₂H₁₅BrSi
• 分子量: 267.241
• InChiKey: ZRCGSHMNVSTLLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(4-溴-2-甲基苯基)乙炔基三甲基硅烷 在 copper(l) iodide 、 四丁基氟化铵 、 碘 、 叔丁基锂 、 二异丙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 4-[2-[4-[2-(4-Ethynyl-3-methylphenyl)ethynyl]phenyl]sulfanylethyl]pyridine
  参考文献：
  名称：

  Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers

  摘要：

  A series of phenylethynyl oligomers (I-V) possessing a ferrocene and thiol at each termini have been synthesized. These oligomers have been designed to overcome the inherent insolubility of this class of complexes by substitution at the phenyl groups with methyl and propoxy substituents. Several new reactions for preparing arenethiol-protected compounds are described. Interestingly, the generation of an arenethiol anion during base- or fluoride-catalyzed deprotection has been characterized.

  DOI：

  10.1021/jo982392m
• 作为产物：
  描述：

  3-溴甲基苯 在 三氯化铝 、 氯磷酸二乙酯 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 2-(4-溴-2-甲基苯基)乙炔基三甲基硅烷
  参考文献：
  名称：

  Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers

  摘要：

  A series of phenylethynyl oligomers (I-V) possessing a ferrocene and thiol at each termini have been synthesized. These oligomers have been designed to overcome the inherent insolubility of this class of complexes by substitution at the phenyl groups with methyl and propoxy substituents. Several new reactions for preparing arenethiol-protected compounds are described. Interestingly, the generation of an arenethiol anion during base- or fluoride-catalyzed deprotection has been characterized.

  DOI：

  10.1021/jo982392m

文献信息

• Photochemical behavior of (diphosphine)(η2-tolane)Pt0 complexes. Part A: Experimental considerations in solution and in the solid state
  作者：Thomas Weisheit、Daniel Escudero、Holm Petzold、Helmar Görls、Leticia González、Wolfgang Weigand

  DOI：10.1039/b925562a

  日期：——

  isolated and characterized by means of spectroscopic methods and additionally by X-ray structure determination (5a–e, 9a–b). In view of potential Caryl–Cethynyl bond activation, we investigated their photochemical behavior in the solid state as well as in solution by irradiating with sunlight. The reactivity towards Caryl–Cethynyl bond activation in the crystalline state and in solution is discussed

  各种系列 （二膦）（η 2 -tolane）的Pt 0 配合物表现出多种取代形式 托兰合成了在Pt中心（9a–b）定义各种咬合角的不同配体（5a–g）和不同的刚性二膦。所有化合物均已通过分光光度法和X射线结构测定（5a–e，9a–b）进行了分离和表征。考虑到潜在的C芳基–ç乙炔键活化，我们研究了它们在固态和溶液中的光化学行为，方法是用阳光照射。对C芳基的反应活性–ç乙炔 讨论了结晶态和溶液中的键活化问题，讨论了与取代基相连的取代基的关系。 托兰配体及其苯环的扭转程度。配合物5a–c和9a带有吸电子溴化物或具有较大的苯环二面角，显示出C芳基的选择性氧化加成–ç乙炔在固态时与Pt中心键合，分别生成配合物6a–c和10a。相比之下，5d–f和9b在相似的条件下被证明是不活泼的，这是因为它们的供电子甲氧基和减少了它们的苯基或甲基的扭曲。吡啶基 的部分 托兰配体。用溶液中的阳光辐照配合物5a和5b可
• Alkynyl Moiety for Triggering 1,2‐Metallate Shifts: Enantiospecific sp ² –sp ³ Coupling of Boronic Esters with <i>p</i> ‐Arylacetylenes
  作者：Venkataraman Ganesh、Marcin Odachowski、Varinder K. Aggarwal

  DOI：10.1002/anie.201703894

  日期：2017.8.7

  The enantiospecific coupling of secondary and tertiary boronic esters to aromatics has been investigated. Using p-lithiated phenylacetylenes and a range of boronic esters coupling has been achieved by the addition of N-bromosuccinimide (NBS). The alkyne functionality of the intermediate boronate complex reacts with NBS triggering the 1,2-migration of the group on boron to carbon giving a dearomatized

  已经研究了仲和叔硼酸酯与芳族化合物的对映体特异性偶联。通过添加N-溴代琥珀酰亚胺（NBS），已使用对位锂化的苯乙炔和一系列硼酸酯实现了偶联。中间体硼酸酯配合物的炔官能团与NBS反应，触发硼上的基团从1,2-迁移到碳上，从而得到脱芳基化的溴丙二烯中间体。此时，新戊基硼酸酯会发生消除和重新芳构化，从而产生偶联产物。然而，使用频哪醇硼酸酯，硼部分迁移至相邻的碳，导致形成结合有邻硼的偶联产物。通过炔烃和硼酸酯官能团的正交转化证明了掺入硼的产物的合成效用。
• Synthesis and Delayed Fluorescent Properties of <scp> <i>p‐Nido</i> ‐Carborane‐Triarylborane </scp> Conjugates with a <scp>Methyl‐Substituted</scp> Phenylene Linker
  作者：Surendran Sujith、Min Hyung Lee

  DOI：10.1002/bkcs.12149

  日期：2021.1

  A series of p‐nido‐carborane‐triarylborane conjugates (nido‐1‐3) in which a methyl group is introduced at the ortho‐position to the carborane cage in the phenylene linker was prepared and characterized. All compounds exhibit broad low‐energy absorptions (λabs = ca. 350–400 nm) attributable to the intramolecular charge transfer transition from the nido‐carborane donor to the (MePh)BMes2 acceptor. Electrochemical

  一系列的对-巢-carborane-三芳基偶联物（巢- 1 - 3），其中甲基是在引入的邻位上的亚苯基连接基碳硼烷笼制备和表征。所有化合物表现出宽的低能量吸收（λ ABS =约350-400纳米）可归因于从该分子内电荷转移过渡巢-carborane施主到（麦菲）BMES 2受体。电化学研究证实，氧化反应发生在氨基碳硼烷上，而硼基部分负责还原。所有的尼多-化合物显示在四氢呋喃（THF）具有良好的光致发光（PL）量子产率（宽绿排放Φ PL = 24％-78％）。具体地讲，从几乎不热活化延迟荧光（TADF）未取代的性质的不同段-conjugates，瞬态PL衰减曲线巢- 1 - 3示出弱TADF的存在（τ d = 0.9-1.4微秒的THF ）。的TADF性质通过下面0.15电子伏特的非常小的单线态-三线态能量分裂进一步支持和在聚（甲基丙烯酸甲酯）还观察到（PMMA）膜掺杂有巢- 1 - 3。
• Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers
  作者：C. J. Yu、Yoochul Chong、Jon Faiz Kayyem、Michael Gozin

  DOI：10.1021/jo982392m

  日期：1999.3.1

  A series of phenylethynyl oligomers (I-V) possessing a ferrocene and thiol at each termini have been synthesized. These oligomers have been designed to overcome the inherent insolubility of this class of complexes by substitution at the phenyl groups with methyl and propoxy substituents. Several new reactions for preparing arenethiol-protected compounds are described. Interestingly, the generation of an arenethiol anion during base- or fluoride-catalyzed deprotection has been characterized.