isocorannulenofuran | 918968-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: isocorannulenofuran
• 英文别名: isocorralenofuran；4-Oxaheptacyclo[14.5.2.02,6.07,20.010,19.013,18.017,21]tricosa-1(21),2,5,7(20),8,10(19),11,13(18),14,16,22-undecaene；4-oxaheptacyclo[14.5.2.02,6.07,20.010,19.013,18.017,21]tricosa-1(21),2,5,7(20),8,10(19),11,13(18),14,16,22-undecaene
• CAS: 918968-92-0
• 化学式: C₂₂H₁₀O
• 分子量: 290.321
• InChiKey: RUGPUQGRQSJRLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isocorannulenofuran 在 diiron nonacarbonyl 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 naphtho[2,3-a]corannulene
  参考文献：
  名称：

  Isocorannulenofuran:  A Versatile Building Block for the Synthesis of Large Buckybowls

  摘要：

  Isocorannulenofuran, synthesized in two steps from accessible bromocorannulene, gives Diels-Alder adducts with benzynes which can be deoxygenated to produce large polycyclic aromatic hydrocarbons (PAHs) combining the bowl-shaped corannulene subunit with planar fragments.

  DOI：

  10.1021/ol0625839
• 作为产物：
  描述：

  25-Oxaoctacyclo[15.5.2.13,6.02,7.08,21.011,20.014,19.018,22]pentacosa-1(22),2(7),4,8(21),9,11(20),12,14(19),15,17,23-undecaene 在 2,6-bis-2-pyridyl-1,2,4,5-tetrazine 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以94%的产率得到isocorannulenofuran
  参考文献：
  名称：

  Isocorannulenofuran:  A Versatile Building Block for the Synthesis of Large Buckybowls

  摘要：

  Isocorannulenofuran, synthesized in two steps from accessible bromocorannulene, gives Diels-Alder adducts with benzynes which can be deoxygenated to produce large polycyclic aromatic hydrocarbons (PAHs) combining the bowl-shaped corannulene subunit with planar fragments.

  DOI：

  10.1021/ol0625839

文献信息

• Towards Molecular Ribbons of Corannulene
  作者：Fabienne Furrer、Anthony Linden、Mihaiela C. Stuparu

  DOI：10.1002/chem.201300830

  日期：2013.9.23

  Herein, we explore the synthesis of corannulene‐based ribbon‐shaped molecules through a repetitive Diels–Alder strategy. For this, appropriate corannulene‐based dienes and dienophiles were identified and synthesized. These building blocks could be combined in a modular way to obtain the dimeric and trimeric segments of the hypothetical molecular ribbons. 1D and 2D NMR measurements, along with crystal‐structure

  本文中，我们通过重复的Diels-Alder策略探索了基于Corannulene的带状分子的合成。为此，鉴定并合成了合适的基于Corannulene的二烯和亲二烯体。这些构件可以以模块化方式组合以获得假设的分子带的二聚体和三聚体链段。1D和2D NMR测量以及晶体结构分析可以确定合成化合物的结构和几何形状。
• A 2:1 Receptor/C₆₀Complex as a Nanosized Universal Joint
  作者：Michael Yanney、Frank R. Fronczek、Andrzej Sygula

  DOI：10.1002/anie.201505327

  日期：2015.9.14

  C60H28 and other corannulene‐based molecular receptors for fullerenes. In addition to the formation of an usual 1:1 C60@catcher inclusion complex, a trimeric C60@(catcher)2 assembly is detected in solutions and in the solid state. X‐ray structure determination reveals a remarkable “universal joint” solvent‐free crystal arrangement of the trimer, with a single fullerene cage wrapped by four corannulene subunits

  Buckycatcher II是一种C 51 H 24烃，在二苯并降冰片二烯系链上带有两个Corannulene钳，在有机溶剂中对C 60的亲和力显着高于最初的Buckycatcher C 60 H 28和其他基于富勒烯的基于氢化萘的烯烃分子受体。除了形成通常的1：1 C 60 @catcher包合物以外，三聚体C 60 @（catcher）2在溶液和固态中检测组装。X射线结构测定揭示了三聚体的显着“万向节”无溶剂晶体排列，单个富勒烯笼包裹着两个协同捕集受体的四个氢化亚环戊烯亚基。
• Bis-corannulenoanthracene: An Angularly Fused Pentacene as a Precursor for Barrelene-Tethered Receptors for Fullerenes
  作者：K. G. Upul R. Kumarasinghe、Frank R. Fronczek、Henry U. Valle、Andrzej Sygula

  DOI：10.1021/acs.orglett.6b01049

  日期：2016.7.1

  Bis-corannulenoanthracene (C50H22, 5) was prepared by the Diels–Alder double cycloaddition of isocorannulenofuran with “bis-benzyne”, followed by deoxygenation of the adducts. Despite the presence of a pentacene core, 5 is stable enough to be isolated and stored. A cycloaddition reaction of 5 with maleic anhydride produces 10 which exhibits strong affinity toward C60, as evidenced by 1H NMR titration experiment

  双- corannulenoanthracene（C 50 ħ 22，5）的制备是通过的isocorannulenofuran的狄尔斯-阿尔德环加成双用“双-苯炔”，接着加合物的脱氧。尽管存在并五苯核，但5足够稳定，可以分离和储存。1 H NMR滴定实验证明，5与马来酸酐的环加成反应生成10，该化合物表现出对C 60的强亲和力。合成10演示了烃的合成的效用5 在制备基于桶状分子的分子夹时，在其带子上带有两个带有极性取代基的苯并Corannulene钳，这将使受体固定在固相支持物上。
• 2-Trimethylsilylcorannulenyl Trifluoromethanesulfonate: An Efficient Precursor for 1,2-Didehydrocorannulene
  作者：Andrzej Sygula、Renata Sygula、Lesya Kobryn

  DOI：10.1021/ol801581z

  日期：2008.9.1

  2-Trimethylsilylcorannulenyl trifluoromethanesulfonate, prepared from bromocorannulene, provides a means for generating of 1,2-didehydrocorannulene (corannulyne) under very mild conditions as demonstrated by the high-yield formation of its adducts with dienes.
• Molecular clips and tweezers with corannulene pincers
  作者：Lesya Kobryn、William P. Henry、Frank R. Fronczek、Renata Sygula、Andrzej Sygula

  DOI：10.1016/j.tetlet.2009.09.177

  日期：2009.12

  Application of the synthetic methodology developed in our laboratory yields molecular clips and tweezers with corannulene pincers and cyclooctadiene or cyclooctatetraene tethers. These highly nonplanar systems possess a potential for binding guest molecules of various sizes. One of the clips, bis(benzocorannulene)[a,e]cyclooctadiene, exists in a 'open' chair conformation encapsulating solvating nitrobenzene in the solid state, while it is expected to prefer an internally pi-pi stacked twist-boat conformation in the gas phase. (c) 2009 Elsevier Ltd. All rights reserved.