1-(2-iodophenylethynyl)-2-(triisopropylsilylethynyl)benzene | 188003-90-9

• 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: 1-(2-iodophenylethynyl)-2-(triisopropylsilylethynyl)benzene
• 英文别名: 2-[2-[2-(2-Iodophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane
• CAS: 188003-90-9
• 化学式: C₂₅H₂₉ISi
• 分子量: 484.495
• InChiKey: LAMBLOSUGSURHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-(2-iodophenylethynyl)-2-(triisopropylsilylethynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 、 三乙胺 为溶剂， 反应 0.5h， 生成 1-Ethynyl-2-[2-[2-[4-(2-ethynylphenyl)buta-1,3-diynyl]phenyl]ethynyl]benzene
  参考文献：
  名称：

  A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

  摘要：

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00229-0
• 作为产物：
  描述：

  邻碘溴苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 、 碘甲烷 作用下， 以 甲醇 为溶剂， 生成 1-(2-iodophenylethynyl)-2-(triisopropylsilylethynyl)benzene
  参考文献：
  名称：

  Versatile Synthetic Route to and DSC Analysis of Dehydrobenzoannulenes:  Crystal Structure of a Heretofore Inaccessible [20]Annulene Derivative

  摘要：

  DOI：

  10.1021/ja964048h

文献信息

• Structure−Property Investigations of Conjugated Thiophenes Fused onto a Dehydro[14]annulene Scaffold
  作者：Matthew J. O’Connor、Robert B. Yelle、Lev N. Zakharov、Michael M. Haley

  DOI：10.1021/jo800225u

  日期：2008.6.1

  A series of 12 thieno-fused macrocycles based on the dehydro[14]annulene framework have been prepared. Studies have focused on the optical and electronic properties of the dehydrobenzothieno[14]annulenes (DBTAs) and dehydrothieno[14]annulenes (DTAs) utilizing NMR spectroscopy, UV−vis spectrophotometry, electrochemistry, and DFT computations. X-ray crystal structures were also obtained for two of the

  基于脱氢[14]环戊烯骨架，已经制备了一系列12个硫杂稠合的大环。利用NMR光谱，紫外可见分光光度法，电化学和DFT计算，研究集中于脱氢苯并噻吩并[14]环烯（DBTA）和脱氢噻吩并[14]环烯（DTA）的光学和电子性质。还为两个大环获得了X射线晶体结构。根据噻吩的相对取向，发现结构-性质关系显着变化。发现这些大环的稳定性，性质和反应性是脱氢环戊烯而不是低聚噻吩的更典型的特征。
• Diatropicity of 3,4,7,8,9,10,13,14-Octadehydro[14]annulenes:  A Combined Experimental and Theoretical Investigation
  作者：Andrew J. Boydston、Michael M. Haley、Richard Vaughan Williams、John R. Armantrout

  DOI：10.1021/jo020463i

  日期：2002.12.1

  increased from one to two to three. This decrease in annulenic ring current is manifested in the alkene proton chemical shifts (0-2 benzenes) as well as the NICS (0-3 benzenes). Comparison of isomeric thiophene-fused annulenes shows further evidence of ring current competition as these allow for observation of intermittent degrees of delocalization throughout the annulenic core. A consistent relationship

  描述了一系列十八氢[14]环戊烯的合成和研究。通过检查来自芳烃融合系统的实验数据以及计算出的与核无关的化学位移（NICS）和键长，研究了这些环的芳香性。苯环与母体系统的融合会导致芳香性逐步降低，因为稠合环的数量从一增加到两到三。环环电流的这种降低表现为烯烃质子化学位移（0-2苯）以及NICS（0-3苯）。异构体噻吩稠合的环烯的比较显示了环电流竞争的进一步证据，因为它们允许观察整个环核的间歇性离域度。
• Diatropicity of Dehydrobenzo[14]annulenes:  Comparative Analysis of the Bond-Fixing Ability of Benzene on the Parent 3,4,7,8,9,10,13,14-Octadehydro[14]annulene
  作者：A. J. Boydston、Michael M. Haley

  DOI：10.1021/ol016764g

  日期：2001.11.1

  [GRAPHICS]We report the synthesis of 3,4,7,8,9,10,13,14-octadehydro[14]annulene (1) and detail a comparative aromaticity study with its benzannelated derivatives (e.g., 2 and 3).
• Versatile Synthetic Route to and DSC Analysis of Dehydrobenzoannulenes:  Crystal Structure of a Heretofore Inaccessible [20]Annulene Derivative
  作者：Michael M. Haley、Michael L. Bell、Jamieson J. English、Charles A. Johnson、Timothy J. R. Weakley

  DOI：10.1021/ja964048h

  日期：1997.3.1
• A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes
  作者：Michael L Bell、Ryan C Chiechi、Charles A Johnson、David B Kimball、Adam J Matzger、W Brad Wan、Timothy J.R Weakley、Michael M Haley

  DOI：10.1016/s0040-4020(01)00229-0

  日期：2001.4

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.