10-(4-甲基苯基)-10H-蒽-9-酮 | 127255-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 10-(4-甲基苯基)-10H-蒽-9-酮
• 中文别名: 9(10H)-蒽酮,10-(4-甲基苯基)-
• 英文名称: 10-(4'-tolyl)anthrone
• 英文别名: 10-p-tolylanthrone；10-(4-Methylphenyl)anthracen-9(10H)-one；10-(4-methylphenyl)-10H-anthracen-9-one
• CAS: 127255-73-6
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: BLKDXKDDHPGACA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10-(4-甲基苯基)-10H-蒽-9-酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以100 mg的产率得到9-(4-methylphenyl)anthracene
  参考文献：
  名称：

  Molecular conformations of 9,9'-bianthryl, di-9-anthrylmethane, and some related twisted anthracene derivatives

  摘要：

  The molecular conformations of 9,9'-bianthryl (1), its 10,10'-diphenyl derivative (2), 9-p-tolylanthracene (3), and 9,10-diphenylanthracene (4) have been investigated by X-ray diffraction. The dihedral angle between the two aromatic ring systems in crystalline 1, in which the asymmetric unit consists of two discrete molecules, was found to be 74.65 (4) and 81.76 (5)-degrees, respectively. In 2, the two anthracene moieties are at an angle of 87.42 (4)-degrees, and the phenyl rings are twisted out of the plane of the adjacent anthracene by 73.2 (1) and 78.1 (1)-degrees. The corresponding torsion angle between the two aromatic ring systems in 3 is 79.59 (8)-degrees. In centrosymmetric 9,10-diphenylanthracene (4), the phenyl rings deviate from coplanarity with the anthracene ring system by 67.63 (5)-degrees. Separating the two anthracene pi-systems of 9,9'-bianthryl by a methylene group increases steric congestion, as was established by X-ray diffraction analysis of di-9-anthrylmethane (5). Its molecular geometry is characterized by a 2-fold axis of symmetry, and the two anthracene pi-systems are in an orthogonal arrangement. Intramolecular hydrogen-hydrogen distances in 5 are as short as 1.93 (3) angstrom, and pi-orbital interaction was found to be topologically facilitated by a contact distance of 2.601 (2) angstrom between the 9- and 9'-carbon atoms. By contrast, in 9-(9-anthrylmethylidene)-9,10-dihydroanthracene (6), which formally derives from 5 by a 1,5-hydrogen shift, the closest intramolecular hydrogen-hydrogen contact is 2.28 (6) angstrom. Relief of steric strain derives from folding of the dihydroanthracene moiety by 39.0 (2)-degrees.

  DOI：

  10.1021/jo00032a050
• 作为产物：
  描述：

  蒽酮 、 甲苯 在 三氯化铝 作用下， 反应 48.0h， 以84%的产率得到10-(4-甲基苯基)-10H-蒽-9-酮
  参考文献：
  名称：

  Nonconventional Friedel-Crafts chemistry. 1. Reaction of .alpha.-tetralone and anthrone with arenes under Friedel-Crafts conditions

  摘要：

  DOI：

  10.1021/jo00300a017

文献信息

• EL-ZOHRY, MAHER F.;EL-KHAWAGA, AHMED M., J. ORG. CHEM., 55,(1990) N3, C. 4036-4039
  作者：EL-ZOHRY, MAHER F.、EL-KHAWAGA, AHMED M.

  DOI：——

  日期：——
• HIRAKAWA, KIYOICHI;MINAMI, YOSHIHITO;HAYASHI, SADAO, J. CHEM. SOC. PERKIN TRANS., 1982, N 2, 577-579
  作者：HIRAKAWA, KIYOICHI、MINAMI, YOSHIHITO、HAYASHI, SADAO

  DOI：——

  日期：——
• Nonconventional Friedel-Crafts chemistry. 1. Reaction of .alpha.-tetralone and anthrone with arenes under Friedel-Crafts conditions
  作者：Maher F. El-Zohry、Ahmed M. El-Khawaga

  DOI：10.1021/jo00300a017

  日期：1990.6
• Molecular conformations of 9,9'-bianthryl, di-9-anthrylmethane, and some related twisted anthracene derivatives
  作者：Hans Dieter Becker、Vratislav Langer、Joachim Sieler、Hans Christian Becker

  DOI：10.1021/jo00032a050

  日期：1992.3

  The molecular conformations of 9,9'-bianthryl (1), its 10,10'-diphenyl derivative (2), 9-p-tolylanthracene (3), and 9,10-diphenylanthracene (4) have been investigated by X-ray diffraction. The dihedral angle between the two aromatic ring systems in crystalline 1, in which the asymmetric unit consists of two discrete molecules, was found to be 74.65 (4) and 81.76 (5)-degrees, respectively. In 2, the two anthracene moieties are at an angle of 87.42 (4)-degrees, and the phenyl rings are twisted out of the plane of the adjacent anthracene by 73.2 (1) and 78.1 (1)-degrees. The corresponding torsion angle between the two aromatic ring systems in 3 is 79.59 (8)-degrees. In centrosymmetric 9,10-diphenylanthracene (4), the phenyl rings deviate from coplanarity with the anthracene ring system by 67.63 (5)-degrees. Separating the two anthracene pi-systems of 9,9'-bianthryl by a methylene group increases steric congestion, as was established by X-ray diffraction analysis of di-9-anthrylmethane (5). Its molecular geometry is characterized by a 2-fold axis of symmetry, and the two anthracene pi-systems are in an orthogonal arrangement. Intramolecular hydrogen-hydrogen distances in 5 are as short as 1.93 (3) angstrom, and pi-orbital interaction was found to be topologically facilitated by a contact distance of 2.601 (2) angstrom between the 9- and 9'-carbon atoms. By contrast, in 9-(9-anthrylmethylidene)-9,10-dihydroanthracene (6), which formally derives from 5 by a 1,5-hydrogen shift, the closest intramolecular hydrogen-hydrogen contact is 2.28 (6) angstrom. Relief of steric strain derives from folding of the dihydroanthracene moiety by 39.0 (2)-degrees.