2,2'-bis(trimethylsilylethynyl)tolane | 120651-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-bis(trimethylsilylethynyl)tolane
• 英文别名: bis{2-[(trimethylsilyl)ethynyl]phenyl}ethyne；1,2-bis(2-(2-trimethylsilylethynyl)phenyl)ethyne；1,2-bis(2-((trimethylsilyl)ethynyl)phenyl)ethyne；2,2'-bis(trimethylsilylethynyl)diphenylacetylene；Trimethyl-[2-[2-[2-[2-(2-trimethylsilylethynyl)phenyl]ethynyl]phenyl]ethynyl]silane
• CAS: 120651-34-5
• 化学式: C₂₄H₂₆Si₂
• 分子量: 370.641
• InChiKey: UJBWGQRTBHLSRB-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  442.2±45.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,2'-bis(trimethylsilylethynyl)tolane 在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 双(2-乙炔基苯基)乙炔
  参考文献：
  名称：

  环状芳乙炔基硅烷的合成，光学性质和光活化杀虫活性

  摘要：

  描述了包含一个或两个三炔口袋的环状芳基乙炔基硅烷的合成和光学性质。将基于这些共轭结构特征的光学特性（如紫外可见光谱，光致发光和量子产率）进行了比较。评估了对白纹伊蚊（Skuse）四龄幼虫的光活化杀虫活性。

  DOI：

  10.1002/cjoc.201190078
• 作为产物：
  描述：

  1,2-diethynylbenzene 在 copper(l) iodide 、 四(三苯基膦)钯 乙基溴化镁 作用下， 以 三乙胺 为溶剂， 反应 5.5h， 生成 2,2'-bis(trimethylsilylethynyl)tolane
  参考文献：
  名称：

  脱氢[12]年环的短途径。

  摘要：

  一种由1,2-二溴苯合成脱水[12]环戊烯的新方法是基于芳基和乙烯基卤化物与末端乙炔的选择性Pd（0）-Cu（1）偶联反应。

  DOI：

  10.1016/s0040-4020(01)89821-5

文献信息

• Aerobic Cu-catalyzed oxidative 1 : 2 coupling of benzynes with terminal alkynes
  作者：Tianhao Lu、Yong Shen、Min Wang、Zibing Zhang、Shijun Li、Chunsong Xie

  DOI：10.1039/d0cc03150j

  日期：——

  Cu-Catalyzed oxidative 1 : 2 couplings of arynes with nucleophilic terminal alkynes under aerobic conditions are described herein. A mechanistic investigation revealed a plausible involvement of an aryl-Cu(III)-generating pathway. By this method, ubiquitous arenediynes can be efficiently assembled in a single step under mild conditions.

  本文描述了在有氧条件下，芳烃与亲核末端炔烃的Cu催化的氧化1：2偶联。一项机械调查显示，可能发生了芳基-铜（III）生成途径。通过这种方法，可以在温和的条件下一步完成无处不在的芳烃。
• Synthesis and structural characterization of five new coordination polymer chain structures using a new, Z-shaped ligand, 2,2′-bis-(4-pyridylethynyl)tolane
  作者：Jeffrey E. Fiscus、Neil Pschirer、Rachael E. Hipp、Andrea M. Goforth、Craig Chapman、Sandra Shotwell、Ralph C. Layland、Mark D. Smith、Uwe H. F. Bunz、Hans-Conrad zur Loye

  DOI：10.1007/s10870-005-2801-8

  日期：2005.2

  Using the new ligand, 2,2′-bis-(4-pyridylethynyl)tolane we have synthesized five new coordination polymers: HgBr2[2,2′-bis-(4-pyridylethynyl)tolane] (1), HgI2[2,2′-bis-(4-pyridylethynyl)tolane] (2), Ni(acetylacetonate)2[2,2′-bis-(4-pyridylethynyl)tolane] (3), Zn(acetylacetonate)2[2,2′-bis-(4-pyridylethynyl)tolane] (4), and Cu(hexafluoro acetylacetonate)2[2,2′-bis-(4-pyridylethynyl)tolane]⋅CHCl3 (5). 2,2′-Bis-(4-pyridyl ethynyl)tolane is a rigid ligand with a Z-shape that promotes the formation of zig-zag chains. Compounds 1– 5 were characterized by single crystal X-ray diffraction; and compounds 1– 3 were additionally characterized by IR, elemental analysis, and thermogravimetric analysis. Compound 1 crystallizes in the monoclinic space group C2/c with a = 29.761(3) Å, b = 5.0531(5) Å, c = 16.7823(15) Å, β = 104.090(2)∘, V = 2447.9(4) Å3, Z = 4. Each mercury is bound to two tolane ligands and two bromine anions, resulting in a tetrahedral coordination environment. Compound 2 crystallizes in the monoclinic space group P2/c, with a = 20.3061(17) Å, b = 5.6303(5) Å, c = 24.5459(19) Å, β = 110.338(2)∘, V = 2631.4(4) Å3, Z = 4. Here also, each mercury is bound to two tolane ligands and two iodine anions in a tetrahedral coordination environment. The ligand orientation differs in compounds 1 and 2 being trans oriented in 1 and cis oriented in 2. Compound 3 crystallizes in the monoclinic space group P21/c with a = 14.5947(14) Å, b = 6.3082(6) Å, c = 18.3939(18) Å, β = 112.112(2)∘, V = 1568.9(3) Å3, Z = 2. Each nickel is bound to two tolane ligands and two bidentate AcAc anions, resulting in an octahedral coordination environment. Compound 4, which is isostructural with 3, also crystallizes in the monoclinic space group P21/c with a = 14.6990(9) Å, b = 6.2724(4) Å, c = 18.6433(11) Å, β = 112.8610(10)∘, V = 1583.86(17) Å3, Z = 2. Compound 5 crystallizes in the triclinic space group P-1 with a = 6.5487(4) Å, b = 11.6471(7) Å, c = 14.3225(9) Å, α = 70.1360(10)∘, β = 89.3990(10)∘, γ = 88.7680(10)∘, V = 1027.18(11) Å3, Z = 1. Each copper in 5 is bound to two tolane ligands and two bidentate hfAcAc anions, resulting in an octahedral coordination environment identical to that found in 3 and 4.

  利用新配体 2,2′-双-(4-吡啶乙炔基)甲苯，我们合成了五种新的配位聚合物：HgBr2[2,2′-双-(4-吡啶乙炔基)甲苯] (1)、HgI2[2,2′-双-(4-吡啶乙炔基)甲苯] (2)、Ni(乙酰丙酮)2[2,2′-双-(4-吡啶乙炔基)甲苯] (3)、Zn(乙酰丙酮)2[2,2′-双-(4-吡啶乙炔基)甲苯](4)和 Cu(六氟乙酰丙酮)2[2,2′-双-(4-吡啶乙炔基)甲苯]⋅CHCl3 (5)。2,2′-双-(4-吡啶基乙炔基)甲苯是一种具有 Z 形的刚性配体，可促进之字链的形成。化合物 1- 5 通过单晶 X 射线衍射进行表征；化合物 1- 3 还通过红外光谱、元素分析和热重分析进行表征。化合物 1 结晶于单斜空间群 C2/c，a = 29.761(3) Å，b = 5.0531(5) Å，c = 16.7823(15) Å，β = 104.090(2)∘，V = 2447.9(4) Å3，Z = 4。每个汞都与两个甲苯配体和两个溴阴离子结合，形成四面体配位环境。化合物 2 在单斜空间群 P2/c 中结晶，a = 20.3061(17)埃，b = 5.6303(5)埃，c = 24.5459(19)埃，β = 110.338(2)∘，V = 2631.4(4)埃3，Z = 4。在这里，每个汞都与两个甲苯配体和两个碘阴离子结合在一个四面体配位环境中。化合物 3 结晶于单斜空间群 P21/c，a=14.5947(14)埃，b=6.3082(6)埃，c=18.3939(18)埃，β=112.112(2)∘，V=1568.9(3)埃3，Z=2。每个镍都与两个甲苯配体和两个双齿 AcAc 阴离子结合，形成八面体配位环境。化合物 4 与 3 同结构，也在单斜空间群 P21/c 中结晶，a = 14.6990(9)埃，b = 6.2724(4)埃，c = 18.6433(11)埃，β = 112.8610(10)∘，V = 1583.86(17)埃3，Z = 2。化合物 5 在三linic 空间群 P-1 中结晶，a = 6.5487(4)埃，b = 11.6471(7)埃，c = 14.3225(9)埃，α = 70.1360(10)∘，β = 89.3990(10)∘，γ = 88.7680(10)∘，V = 1027.18(11)埃3，Z = 1。5 中的每个铜都与两个甲苯配体和两个双齿 hfAcAc 阴离子结合，形成了与 3 和 4 中相同的八面体配位环境。
• Chirality Sensing With Stereodynamic Biphenolate Zinc Complexes
  作者：Keith W. Bentley、Zeus A. Santos、Mary J. Weiss、Christian Wolf

  DOI：10.1002/chir.22489

  日期：2015.10

  polyarylacetylene framework with terminal phenol groups were synthesized. Reaction with diethylzinc gives stereodynamic complexes that undergo distinct asymmetric transformation of the first kind upon binding of chiral amines and amino alcohols. The substrate‐to‐ligand chirality imprinting at the zinc coordination sphere results in characteristic circular dichroism signals that can be used for direct enantiomeric

  合成了由具有末端酚基的助熔聚芳基乙炔骨架组成的两个双齿配体。与二乙基锌反应生成立体动力学复合物，该复合物在手性胺和氨基醇结合后会经历明显的第一类不对称转化。锌配位体上的底物-配体手性印迹产生了特征性的二向色性信号，可用于直接对映体过量（ee）分析。与传统的高效液相色谱方法相比，这种化学传感方法具有以少量样品进行高通量ee筛选的潜力，并减少了溶剂浪费。手性27：700–707，2015。©2015 Wiley Periodicals，Inc.
• Sulfoxide-Induced Homochiral Folding of <i>ortho</i> -Phenylene Ethynylenes (<i>o</i> -OPEs) by Silver(I) Templating: Structure and Chiroptical Properties
  作者：Sandra Resa、Delia Miguel、Santiago Guisán-Ceinos、Giuseppe Mazzeo、Duane Choquesillo-Lazarte、Sergio Abbate、Luis Crovetto、Diego J. Cárdenas、M. Carmen Carreño、María Ribagorda、Giovanna Longhi、Antonio J. Mota、Luis Álvarez de Cienfuegos、Juan M. Cuerva

  DOI：10.1002/chem.201704897

  日期：2018.2.21

  family of homochiral silver complexes based on carbophilic interactions with ortho‐phenylene ethynylene (o‐OPE) scaffolds containing up to two silver atoms are described. These compounds represent a unique class of complexes with chirality at the metal. Chiral induction is based on the inclusion of chiral sulfoxides, which allow efficient transfer of chirality to the helically folded o‐OPE, leading to

  基于与最多包含两个银原子的邻亚苯基亚乙炔基（o- OPE）支架的亲脂性相互作用，描述了一个新的同手性银配合物家族。这些化合物代表一类独特的在金属上具有手性的络合物。手性诱导是基于包含手性亚砜，其允许手性有效地传输到螺旋折叠的ö‐ OPE，导致圆偏振发光（CPL）和振动圆二色性（VCD）活性化合物。在银（I）阳离子的存在下，嗜碳相互作用占主导地位，这促进了具有确定螺旋度的螺旋结构。这是在非生物折叠剂有吸引力的领域中使用这种相互作用的非常稀有的例子之一。开关事件已通过使用各种按摩疗法技术（包括圆二色性，CPL和VCD）进行了广泛研究，并且代表了文献中描述的少数CPL开关之一。
• (η6-[7]Heliphene)tricarbonylchromium via an Optimized Preparation of [7]Heliphene
  作者：K. Vollhardt、Daniel Holmes、Sang Lee、Sabine Lotz、Son Nguyen、Gaston Schaller、Rachel Schmidt-Radde

  DOI：10.1055/s-0034-1380535

  日期：——

  Optimized procedures to [7]heliphene are described that allowed the synthesis of ((6)-[7]heliphene)tricarbonylchromium and a preliminary exploration of its chemical behavior. DFT calculations provide structural and energetic information on this complex and its haptomeric isomers. Attempts to prepare the corresponding ([7]heliphene)chromium sandwich failed so far, but DFT evidence is presented to indicate that the target should be accessible.