2,3-bis(pentamethylphenyl)bicyclo[2.2.2]oct-2-ene | 180578-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2,3-bis(pentamethylphenyl)bicyclo[2.2.2]oct-2-ene
• 英文别名: 2,3-Bis(2,3,4,5,6-pentamethylphenyl)-bicyclo[2.2.2]oct-2-ene；2,3-bis(2,3,4,5,6-pentamethylphenyl)bicyclo[2.2.2]oct-2-ene
• CAS: 180578-79-4
• 化学式: C₃₀H₄₀
• 分子量: 400.648
• InChiKey: WOTZUBXKWFUDMG-UHFFFAOYSA-N

物化性质

• 沸点：
  543.8±45.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  2,3-bis(pentamethylphenyl)bicyclo[2.2.2]oct-2-ene 在 nitric oxide 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Novel Arene Receptors as Nitric Oxide (NO) Sensors

  摘要：

  Nitric oxide sensors are based on the reversible, specific, and efficient binding to various types of arene receptors via intermolecular complexes, which are characterized by complete electron delocalization and strong interaction between the donor and acceptor moieties.

  DOI：

  10.1021/ja020217o
• 作为产物：
  描述：

  在 nitric oxide 作用下， 以 二氯甲烷 为溶剂， 生成 2,3-bis(pentamethylphenyl)bicyclo[2.2.2]oct-2-ene
  参考文献：
  名称：

  Novel Arene Receptors as Nitric Oxide (NO) Sensors

  摘要：

  Nitric oxide sensors are based on the reversible, specific, and efficient binding to various types of arene receptors via intermolecular complexes, which are characterized by complete electron delocalization and strong interaction between the donor and acceptor moieties.

  DOI：

  10.1021/ja020217o

文献信息

• Vicinal-diaryl interactions in stilbenoid hydrocarbons as observed in the through-space charge delocalization of their cation radicals
  作者：Rajendra Rathore、Jay K Kochi

  DOI：10.1139/v99-081

  日期：1999.6.1

  The conformational preference of vicinal or 1,2-phenyl groups is probed in two classes of ring-substituted 1,2-diphenylbicyclooctene (stilbenoid) hydrocarbons 1a-1d and 2a-2c. UV-vis spectroscopy reveals, and X-ray crystallography verifies, the intramolecular (edge-to-face) orientation for the phenyl-phenyl interaction in stilbenoids 1a-1d. Most importantly, when two pairs of ortho-methyl substituents are present, the cofacial phenyl groups in the stilbenoid donors are established by X-ray crystallography and spectrally observed in the cation radicals (2a^+.-2c^+.) by the appearance of new bands with strong absorptions in the near IR with λ_max = 1100-1315 nm, analogous to those previously observed in intermolecular (aromatic) interactions of aromatic cation radicals.Key words: stilbenoid hydrocarbon, cation radical, aryl-aryl interaction.

  在两类环替代的1,2-二苯基双环辛烷（stilbenoid）碳氢化合物1a-1d和2a-2c中，探测了邻位或1,2-苯基的构象偏好。UV-vis光谱揭示了，X射线晶体学证实了，stilbenoid 1a-1d中苯-苯相互作用的分子内（边缘对面）取向。最重要的是，当存在两对邻甲基取代基时，在X射线晶体学中建立了stilbenoid供体中的同面苯基团，并通过在阳离子自由基（2a+. -2c+.）中出现具有强吸收的新带，其λmax = 1100-1315 nm，类似于以前观察到的芳香族阳离子自由基的分子间（芳香族）相互作用。关键词：stilbenoid碳氢化合物，阳离子自由基，芳基-芳基相互作用。
• An Efficient Venus Flytrap for the Reversible Binding of Nitric Oxide
  作者：Rajendra Rathore、Sergey V. Lindeman、Jay K. Kochi

  DOI：10.1002/(sici)1521-3773(19980619)37:11<1585::aid-anie1585>3.0.co;2-w

  日期：1998.6.19

  Remarkably efficient reversible binding of nitric oxide (NO) by the stilbenoid derivative 1 is observed (K>3×106 M-1 ). This noncovalent interaction is readily controlled by simple oxidation and reduction.

  观察到二苯乙烯类衍生物1对一氧化氮（NO）的显着有效的可逆结合（K＞ 3×10 6 M -1）。这种非共价相互作用很容易通过简单的氧化和还原来控制。
• Efficient Hydrogenation of Sterically Hindered Olefins with Borane−Methyl Sulfide Complex
  作者：R. Rathore、U. Weigand、J. K. Kochi

  DOI：10.1021/jo960357e

  日期：1996.1.1

  Sterically hindered olefins are efficiently reduced to the corresponding alkanes by the borane-methyl sulfide (BMS) complex at room temperature (or below) in dichloromethane containing a mild one-electron oxidant (such as an aromatic cation radical) or by the passage of an anodic current. In an alternative procedure, the hydrogenation of the same (electron-rich) olefins with the EMS complex (in the absence of a one-electron oxidant) is also carried out-in the presence of a strong Bronsted acid (such as HBF4). In the oxidative activation, olefin cation radicals are the first observable intermediates, and separate experiments (including transient electrochemistry) confirm the facile reduction of the olefin cation radical by borane to produce the corresponding alkane. The direct protonation of olefins produces carbocationic intermediates which are also efficiently reduced by borane to the corresponding alkanes. The intermediacy of both olefin cation radicals and carbocations in the hydrogenation procedure with borane is discussed.
• Silver(I) Complexation of (Poly)aromatic Ligands. Structural Criteria for Depth Penetration into <i>cis</i>-Stilbenoid Cavities
  作者：S. V. Lindeman、R. Rathore、J. K. Kochi

  DOI：10.1021/ic000770b

  日期：2000.12.1

  Silver(I) complexes with aromatic donors an thoroughly analyzed (with aid of the Cambridge Crystallographic Database) to identify the basic structural factors inherent to the bonding of an arene ligand. Most strikingly, the distance parameter d (which simply measures the normal separation of Ag from the mean aromatic plane) is singularly invariant at d = 2.41 +/- 0.05 Angstrom for all silver/arene complexes, independent of the hapticity (eta (1) or eta (2)), hybridization, or multiple coordination. As such, a systematic series of stilbenoid ligands has been successfully designed to precisely modulate the penetration of silver(I) into the ligand cleft, and a multicentered poly(arene) ligand (X) designed to form a one-dimensional assembly of Ag/arene units. Simply stated, the depth penetration of silver(I) into the aromatic cavities of various cis-stilbenoid donors can be precisely predicted with a single parameter gamma that measures the separation of the two cofacial aryl groups comprising the cleft. This simple geometric consideration must be taken into account in any successful-design of novel (poly)aromatic ligands for silver(I) complexation to constitute new molecular architectures.