1,2:7,8:13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1,2:7,8:13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne
• 英文别名: dehydrobenzo[24]annulene；Pentacyclo[34.4.0.06,11.016,21.026,31]tetraconta-1(40),6,8,10,16,18,20,26,28,30,36,38-dodecaen-2,4,12,14,22,24,32,34-octayne；pentacyclo[34.4.0.06,11.016,21.026,31]tetraconta-1(40),6,8,10,16,18,20,26,28,30,36,38-dodecaen-2,4,12,14,22,24,32,34-octayne
• 化学式: C₄₀H₁₆
• 分子量: 496.567
• InChiKey: XLVXDLPDSWIIFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  邻碘溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 copper diacetate 、 四丁基氟化铵 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 三乙胺 为溶剂， 反应 0.5h， 生成 1,2:7,8:13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne
  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

文献信息

• Synthesis of Expanded Graphdiyne Substructures
  作者：W. Brad Wan、Stephen C. Brand、Joshua J. Pak、Michael M. Haley

  DOI：10.1002/1521-3765(20000602)6:11<2044::aid-chem2044>3.0.co;2-y

  日期：2000.6.2

  Graphdiyne (1) is a member of a novel family of interesting and potentially important allotropes of carbon. Reported herein are the synthesis and spectroscopic characterization of model substructures 2-6. The macrocycles were prepared by the intramolecular cyclization of suitable alpha,omega-polyynes. Key to the success of this approach was the development of an in situ protiodesilylation/alkynylation

  Graphdiyne（1）是一个有趣且潜在重要的碳同素异形体新家族的成员。本文报道的是模型子结构2-6的合成和光谱表征。大环通过合适的α，ω-聚炔的分子内环化制备。该方法成功的关键是利用反应性苯基丁二炔合成子进行原位丙二甲硅烷基化/炔基化反应。迄今为止，这种新方法可以制备石墨二炔网络中最大，最完整的子结构（3-6）。
• Selective Deprotection of Me₃Si-/Ph₂P(O)-protected Arylalkynes: Methyl Grignard Reagent-promoted Dephosphorylation of Ph₂P(O)-protected Alkynes
  作者：Lifen Peng、Feng Xu、Kenta Shinohara、Akihiro Orita、Junzo Otera

  DOI：10.1246/cl.140579

  日期：2014.10.5

  A Ph2P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me3Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal alkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me3Si-/Ph2P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethynylenes and unsymmetrically substituted ditriazol.

  一种Ph2P(O)保护的炔烃在THF中用MeMgBr处理后发生去磷酸化，Me3Si保护未受到影响。该去磷酸化后紧接着与芳基卤化物进行的过渡金属催化偶联反应以一锅法进行，从而获得所需的偶联产物。选择性去保护Me3Si-/Ph2P(O)保护的炔烃使得扩展π系统的合成变得简便，例如环状苯乙炔和不对称取代的二三唑。
• Synthesis and crystal structure of 1,2:7,8 : 13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne
  作者：Li Guo、John D. Bradshaw、Claire A. Tessier、Wiley J. Youngs

  DOI：10.1039/c39940000243

  日期：——

  The title compound has been synthesized in a relatively high yield by the Glaser coupling reaction and characterized by X-ray crystallography and spectroscopy.

  标题化合物是通过格拉塞偶联反应以较高产率合成的，并通过 X 射线晶体学和光谱学进行了表征。
• 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.