2-(4-((4-methoxyphenyl)ethynyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1190376-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-((4-methoxyphenyl)ethynyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[4-(4-Methoxy-phenylethynyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane；2-[4-[2-(4-methoxyphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1190376-24-9
• 化学式: C₂₁H₂₃BO₃
• 分子量: 334.223
• InChiKey: RRYKLXOOBFDYDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-((4-methoxyphenyl)ethynyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 2-溴-1-甲基-1H-咪唑-4,5-二甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以56%的产率得到2-[4-(4-methoxyphenylethynyl)phenyl]-1-methyl-1H-imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Push-pull molecules with a systematically extended π-conjugated system featuring 4,5-dicyanoimidazole

  摘要：

  Eighteen chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, a systematically enlarged pi-conjugated spacer and methoxy and N,N-dimethylamino groups as donors were synthesised and characterised by X-ray analysis, electrochemistry, UV-Vis and fluorescence spectroscopy whilst NLO properties were calculated Quantitative relationships between measured properties and structural features of the chromophores were also evaluated (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.dyepig.2009.10.004
• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 2-(4-((4-methoxyphenyl)ethynyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  新型D–π–A–π–D型芳烃阳离子环戊二烯基铁配合物的合成和光学性质†

  摘要：

  通过亲核取代和Suzuki偶联反应成功地将二苯基乙炔基生色团引入阳离子环戊二烯基铁配合物的芳烃配体中。获得了三种具有对称二（4-甲氧基-苯基乙炔基）发色团（CFS）的新型阳离子环戊二烯基铁配合物，并通过IR，1 H NMR，13 C NMR和MS对其进行了完全表征。使用苯基乙炔基键对获得的分子的线性和非线性光学性质进行了调节。紫外-可见吸收光谱表明，通过用苯乙炔垫片增加的缀合导致在吸收带红移和氯氟烃一个较强的吸收比以前报道的（η 6 -cumene）（η 5-环戊二烯基）六氟磷酸铁（I-261）。这些交叉共轭的D–π–A–π–D型化合物还表现出比I-261更大的三阶非线性磁化率。

  DOI：

  10.1039/c5ra08989a

文献信息

• Convenient methods for preparing π-conjugated linkers as building blocks for modular chemistry
  作者：Jiří Kulhánek、Filip Bureš、Miroslav Ludwig

  DOI：10.3762/bjoc.5.11

  日期：——

  and optimized procedures for preparing extended pi-conjugated linkers are described. Either unsubstituted or 4-donor substituted pi-linkers bearing a styryl, biphenyl, phenylethenylphenyl, and phenylethynylphenyl pi-conjugated backbone are functionalized with boronic pinacol esters as well as with terminal acetylene moieties allowing their further use as building blocks in Suzuki-Miyaura or Sonogashira

  描述了用于制备扩展π共轭接头的简单、直接和优化的程序。带有苯乙烯基、联苯、苯基乙烯基苯基和苯基乙炔基苯基π-共轭主链的未取代或4-供体取代的π-连接体用硼频哪醇酯以及末端乙炔部分进行功能化，允许它们进一步用作Suzuki-Miyaura或Sonogashira中的结构单元偶联反应。
• An Improved Protocol for the Synthesis of [(η⁴-C₄R₄)Co(η⁵-C₅H₅)] Complexes
  作者：Guillaume Bertrand、Ludovic Tortech、Denis Fichou、Max Malacria、Corinne Aubert、Vincent Gandon

  DOI：10.1021/om200662g

  日期：2012.1.9

  The reaction of bulky alkynes C2R2 with (η5-C5H5)Co(CO)(dimethyl fumarate) under microwave irradiation provides complexes of the type [(η4-C4R4)Co(η5-C5H5)] in good to excellent yields. This protocol represents a significant improvement over those reported previously. In particular, the formation of insertion products such as cyclopentadienones or cyclohexadienes can be avoided. In addition, because

  笨重炔C的反应2 - [R 2与（η 5 -C 5 H ^ 5）的Co（CO）（富马酸二甲酯）在微波辐射下提供了式[（η的络合物4 -C 4 - [R 4）的Co（η 5 - C 5 H 5）]，收率良好。该协议表示对以前报告的协议的重大改进。特别地，可以避免形成插入产物，例如环戊二烯酮或环己二烯。此外，由于特殊的稳定性（的η 5 -C 5 H ^ 5）Co（CO）（富马酸二甲酯），反应可在粗溶剂中进行。容易进入[（η 4 -C 4 - [R 4）的Co（η 5 -C 5 H ^ 5）]配合物刺激的反应性的研究，特别是交叉偶联条件下进行。
• Alkyne Semihydrogenation with a Well-Defined Nonclassical Co–H₂ Catalyst: A H₂ Spin on Isomerization and <i>E</i>-Selectivity
  作者：Kenan Tokmic、Alison R. Fout

  DOI：10.1021/jacs.6b08128

  日期：2016.10.19

  The reactivity of a co(I)-H-2 complex was extended toward the semihydrogenation of internal alkynes. Under ambient temperatures and moderate pressures of H-2, a broad scope of alkynes were semihydrogenated using a Co-I-N-2 precatalyst, resulting in the formation of trans-alkene products. Furthermore, mechanistic studies using H-1, H-2, and parahydrogen induced polarization (PHIP) transfer NMR spectroscopy revealed cis -hydrogenation of the alkyne occurs first. The Co-mediated alkene isomerization afforded the E-selective products from a broad group of alkynes with good yields and E/Z selectivity.
• Synthesis and optical properties of novel D–π–A–π–D type cationic cyclopentadienyliron complexes of arenes
  作者：B. D. Zhao、G. L. Li、Y. Z. Shi、H. Q. Zhang、T. Wang

  DOI：10.1039/c5ra08989a

  日期：——

  Diphenylethynyl chromophores were successfully introduced into the arene ligands of cationic cyclopentadienyliron complexes through nucleophilic substitution and Suzuki coupling reactions. Three novel cationic cyclopentadienyliron complexes with symmetrical di(4-methoxy-phenylethynyl) chromophores (CFSs) were obtained and completely characterized by IR, 1H NMR, 13C NMR, and MS. The linear and nonlinear

  通过亲核取代和Suzuki偶联反应成功地将二苯基乙炔基生色团引入阳离子环戊二烯基铁配合物的芳烃配体中。获得了三种具有对称二（4-甲氧基-苯基乙炔基）发色团（CFS）的新型阳离子环戊二烯基铁配合物，并通过IR，1 H NMR，13 C NMR和MS对其进行了完全表征。使用苯基乙炔基键对获得的分子的线性和非线性光学性质进行了调节。紫外-可见吸收光谱表明，通过用苯乙炔垫片增加的缀合导致在吸收带红移和氯氟烃一个较强的吸收比以前报道的（η 6 -cumene）（η 5-环戊二烯基）六氟磷酸铁（I-261）。这些交叉共轭的D–π–A–π–D型化合物还表现出比I-261更大的三阶非线性磁化率。
• Push-pull molecules with a systematically extended π-conjugated system featuring 4,5-dicyanoimidazole
  作者：Jiří Kulhánek、Filip Bureš、Oldřich Pytela、Tomáš Mikysek、Jiří Ludvík、Aleš Růžička

  DOI：10.1016/j.dyepig.2009.10.004

  日期：2010.4

  Eighteen chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, a systematically enlarged pi-conjugated spacer and methoxy and N,N-dimethylamino groups as donors were synthesised and characterised by X-ray analysis, electrochemistry, UV-Vis and fluorescence spectroscopy whilst NLO properties were calculated Quantitative relationships between measured properties and structural features of the chromophores were also evaluated (C) 2009 Elsevier Ltd. All rights reserved