1,1'-bianthryl | 1104-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,1'-bianthryl
• 英文别名: bianthracene；(+/-)-Bianthryl-(1.1')；Dianthracen；1,1'-Bianthracene；1-anthracen-1-ylanthracene
• CAS: 1104-41-2
• 化学式: C₂₈H₁₈
• 分子量: 354.451
• InChiKey: XWSSEFVXKFFWLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• 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：

  1,1'-bianthryl 、 以 氘代乙腈 为溶剂， 生成
  参考文献：
  名称：

  Temperature Controls Guest Uptake and Release from Zn₄L₄ Tetrahedra

  摘要：

  We report the preparation of triazatruxene-faced tetrahedral cage 1, which exhibits two diastereomeric configurations (T1 and T2) that differ in the handedness of the ligand faces relative to that of the octahedrally coordinated metal centers. At lower temperatures, T1 is favored, whereas T2 predominates at higher temperatures. Host-guest studies show that T1 binds small aliphatic guests, whereas T2 binds larger aromatic molecules, with these changes in binding preference resulting from differences in cavity size and degree of enclosure. Thus, by a change in temperature the cage system can be triggered to eject one bound guest and take up another.

  DOI：

  10.1021/jacs.9b07307
• 作为产物：
  描述：

  [1,1']bianthryl-9,10,9',10'-tetraone 在 ammonium hydroxide 、 锌 作用下， 反应 3.0h， 以14%的产率得到1,1'-bianthryl
  参考文献：
  名称：

  Static and dynamic stereochemistry of 1,1?-bi(9,10-dihydro-9,10-ethano-anthryl)

  摘要：

  The title compound 2 was prepared either by highpressure reaction of 1,1'-bianthryl with ethylene or by coupling of 1-bromo-9,10-dihydro-9,10-ethanoanthracene (4). Both syntheses afforded a mixture of diastereoisomers (meso 2 a and racemate 2 b) in a ratio of 1.5:1 and 2.3:1, respectively. Configurational assignment was possible both from the H-1- and C-13-NMR spectra and by coupling of laevorotatory 4 (accessibly by enantioselective chromatography on triacetyl cellulose in ethanol) to laevorotatory 2 b. (+)-4 was transformed into the dextrorotatory carboxylic acid (+)-5 of known configuration (9 R) thus establishing the configuration of (+)-4 as (9 R) too and hence the centrochirality in (-)-2 b as (9 S)(9' S). The racemic form 2 b is a conformational (appr. 1.8:1) mixture of two rotamers.The rotational barrier was established as DELTA-G# = 92 - 95 kJ mol-1 (depending on the temperature) both by H-1-NMR and CD kinetics (based on equilibration of the separated optically active rotamers of racem. 2). For the latter preferred conformations were assumed allowing the assignment of the axial chirality: e.g. (-)-(9 S)(R)a(9' S) for the main rotamer of (-)-2 b [and (-)(9 S)(S)a(9' S) for the underpopulated one].All assumptions were confirmed by X-ray crystal structure analyses of 2 a and the main rotamer of 2 b with torsional angles around the 1,1'-bonds of -111.1 and -121.2-degrees, respectively.

  DOI：

  10.1007/bf00811118

文献信息

• 63. The symmetrical dianthryls. Part I
  作者：F. Bell、D. H. Waring

  DOI：10.1039/jr9490000267

  日期：——
• 337. The symmetrical dianthryls. Part II
  作者：F. Bell、D. H. Waring

  DOI：10.1039/jr9490001579

  日期：——
• Temperature Controls Guest Uptake and Release from Zn₄L₄ Tetrahedra
  作者：Dawei Zhang、Tanya K. Ronson、Songül Güryel、John D. Thoburn、David J. Wales、Jonathan R. Nitschke

  DOI：10.1021/jacs.9b07307

  日期：2019.9.18

  We report the preparation of triazatruxene-faced tetrahedral cage 1, which exhibits two diastereomeric configurations (T1 and T2) that differ in the handedness of the ligand faces relative to that of the octahedrally coordinated metal centers. At lower temperatures, T1 is favored, whereas T2 predominates at higher temperatures. Host-guest studies show that T1 binds small aliphatic guests, whereas T2 binds larger aromatic molecules, with these changes in binding preference resulting from differences in cavity size and degree of enclosure. Thus, by a change in temperature the cage system can be triggered to eject one bound guest and take up another.
• Static and dynamic stereochemistry of 1,1?-bi(9,10-dihydro-9,10-ethano-anthryl)
  作者：Karl Schl�gl、Zhi Li、Christoph Kratky

  DOI：10.1007/bf00811118

  日期：1991.12

  The title compound 2 was prepared either by highpressure reaction of 1,1'-bianthryl with ethylene or by coupling of 1-bromo-9,10-dihydro-9,10-ethanoanthracene (4). Both syntheses afforded a mixture of diastereoisomers (meso 2 a and racemate 2 b) in a ratio of 1.5:1 and 2.3:1, respectively. Configurational assignment was possible both from the H-1- and C-13-NMR spectra and by coupling of laevorotatory 4 (accessibly by enantioselective chromatography on triacetyl cellulose in ethanol) to laevorotatory 2 b. (+)-4 was transformed into the dextrorotatory carboxylic acid (+)-5 of known configuration (9 R) thus establishing the configuration of (+)-4 as (9 R) too and hence the centrochirality in (-)-2 b as (9 S)(9' S). The racemic form 2 b is a conformational (appr. 1.8:1) mixture of two rotamers.The rotational barrier was established as DELTA-G# = 92 - 95 kJ mol-1 (depending on the temperature) both by H-1-NMR and CD kinetics (based on equilibration of the separated optically active rotamers of racem. 2). For the latter preferred conformations were assumed allowing the assignment of the axial chirality: e.g. (-)-(9 S)(R)a(9' S) for the main rotamer of (-)-2 b [and (-)(9 S)(S)a(9' S) for the underpopulated one].All assumptions were confirmed by X-ray crystal structure analyses of 2 a and the main rotamer of 2 b with torsional angles around the 1,1'-bonds of -111.1 and -121.2-degrees, respectively.