Nonadecacyclo[47.5.2.27,13.225,31.04,53.05,42.06,23.08,12.09,22.010,19.011,16.024,41.026,30.027,40.028,37.029,34.043,52.046,51.050,54]hexaconta-1(54),2,4(53),5,7,9(22),10(19),11(16),12,14,17,20,23,25,27(40),28(37),29(34),30,32,35,38,41,43(52),44,46(51),47,49,55,57,59-triacontaene | 1352996-11-2

• 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: Nonadecacyclo[47.5.2.27,13.225,31.04,53.05,42.06,23.08,12.09,22.010,19.011,16.024,41.026,30.027,40.028,37.029,34.043,52.046,51.050,54]hexaconta-1(54),2,4(53),5,7,9(22),10(19),11(16),12,14,17,20,23,25,27(40),28(37),29(34),30,32,35,38,41,43(52),44,46(51),47,49,55,57,59-triacontaene
• CAS: 1352996-11-2
• 化学式: C₆₀H₂₄
• 分子量: 744.851
• InChiKey: VHKYNDNQLOEQMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  60
• 可旋转键数：
  0
• 环数：
  19.0
• 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

• 作为反应物：
  描述：

  2-trimethylsilylcorannulenyl triflate 、 Nonadecacyclo[47.5.2.27,13.225,31.04,53.05,42.06,23.08,12.09,22.010,19.011,16.024,41.026,30.027,40.028,37.029,34.043,52.046,51.050,54]hexaconta-1(54),2,4(53),5,7,9(22),10(19),11(16),12,14,17,20,23,25,27(40),28(37),29(34),30,32,35,38,41,43(52),44,46(51),47,49,55,57,59-triacontaene 在 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到
  参考文献：
  名称：

  Corannulene Subunit Acts as a Diene in a Cycloaddition Reaction: Synthesis of C₈₀H₃₂ Corannulyne Tetramer

  摘要：

  Distortion of six-membered rings in corannulene subunits of corannulyne (1,2-didehydrocorannulene) cyclotrimer activates the system for a cycloaddition reaction with another corannulyne unit. This unprecedented cycloaddition in which a corannulene fragment acts as a diene produces the largest oligomer of corannulyne reported to date. X-ray crystallography reveals the highly nonplanar structure of the tetramer which exhibits conformational and optical absorption properties very different from those of the cyclotrimer.

  DOI：

  10.1021/ol302274j
• 作为产物：
  描述：

  2-trimethylsilylcorannulenyl triflate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 cesium fluoride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 以40%的产率得到Nonadecacyclo[47.5.2.27,13.225,31.04,53.05,42.06,23.08,12.09,22.010,19.011,16.024,41.026,30.027,40.028,37.029,34.043,52.046,51.050,54]hexaconta-1(54),2,4(53),5,7,9(22),10(19),11(16),12,14,17,20,23,25,27(40),28(37),29(34),30,32,35,38,41,43(52),44,46(51),47,49,55,57,59-triacontaene
  参考文献：
  名称：

  Corannulyne 的 Cyclotrimerization：空间位阻调节 Corannulene 碗的反转障碍

  摘要：

  X 射线晶体结构测定和 HDFT 计算表明，钯催化的由 2-三甲基甲硅烷基三氟甲磺酸基三氟甲磺酸酯生成的二甲萘醌环三聚反应产生了一种 C60H24 烃，它更喜欢 C1 对称的高度非平面“扭曲”构象。它的三个冠烯亚基在理想化的 D3h 对称性中相同，表现出截然不同的反转势垒（从 8.4 到 17.3 kcal mol-1），由高度不对称结构内的空间拥挤调节。具有最低活化势垒的蒌烯单元的碗对碗反转导致分子的假旋转并产生仅显示 12 个不同质子信号的 1H NMR 光谱。选定的 NMR 信号的线形分析给出了 8.5-8.6 kcal mol-1 的势垒估计。

  DOI：

  10.1002/ejoc.201101374

文献信息

• Cyclotrimerization of Corannulyne: Steric Hindrance Tunes the Inversion Barriers of Corannulene Bowls
  作者：Michael Yanney、Frank R. Fronczek、William P. Henry、Debbie J. Beard、Andrzej Sygula

  DOI：10.1002/ejoc.201101374

  日期：2011.11

  to 17.3 kcal mol–1), tuned by the steric congestion inside the highly dissymmetric structure. Bowl-to-bowl inversion of the corannulene unit with the lowest activation barrier results in pseudorotation of the molecule and gives rise to a 1H NMR spectrum exhibiting only 12 distinct proton signals. The line-shape analysis of selected NMR signals gave an estimation of the barrier at 8.5–8.6 kcal mol–1

  X 射线晶体结构测定和 HDFT 计算表明，钯催化的由 2-三甲基甲硅烷基三氟甲磺酸基三氟甲磺酸酯生成的二甲萘醌环三聚反应产生了一种 C60H24 烃，它更喜欢 C1 对称的高度非平面“扭曲”构象。它的三个冠烯亚基在理想化的 D3h 对称性中相同，表现出截然不同的反转势垒（从 8.4 到 17.3 kcal mol-1），由高度不对称结构内的空间拥挤调节。具有最低活化势垒的蒌烯单元的碗对碗反转导致分子的假旋转并产生仅显示 12 个不同质子信号的 1H NMR 光谱。选定的 NMR 信号的线形分析给出了 8.5-8.6 kcal mol-1 的势垒估计。
• Corannulene Subunit Acts as a Diene in a Cycloaddition Reaction: Synthesis of C₈₀H₃₂ Corannulyne Tetramer
  作者：Michael Yanney、Frank R. Fronczek、Andrzej Sygula

  DOI：10.1021/ol302274j

  日期：2012.9.21

  Distortion of six-membered rings in corannulene subunits of corannulyne (1,2-didehydrocorannulene) cyclotrimer activates the system for a cycloaddition reaction with another corannulyne unit. This unprecedented cycloaddition in which a corannulene fragment acts as a diene produces the largest oligomer of corannulyne reported to date. X-ray crystallography reveals the highly nonplanar structure of the tetramer which exhibits conformational and optical absorption properties very different from those of the cyclotrimer.