1,1',8,8'-tetrachloro-9,9'-bianthracene-10,10'(9H,9'H)-dione | 406912-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,1',8,8'-tetrachloro-9,9'-bianthracene-10,10'(9H,9'H)-dione
• 英文别名: 1,1',8,8'-tetrachloro-9,9'-bianhracene-10,10'-dione；1,8,1',8'-tetrachloro-9H,9'H-[9,9']bianthryl-10,10'-dione；1,8,1',8'-Tetrachlor-9H,9'H-[9,9']bianthryl-10,10'-dion；1.8.1'.8'-Tetrachlor-10.10'-dioxo-9.10.9'.10'-tetrahydro-dianthranyl-(9.9')；1.8.1'.8'-Tetrachlor-dihydrodianthron；Vpoujzssbsvpaj-uhfffaoysa-；4,5-dichloro-10-(1,8-dichloro-10-oxo-9H-anthracen-9-yl)-10H-anthracen-9-one
• CAS: 406912-03-6
• 化学式: C₂₈H₁₄Cl₄O₂
• 分子量: 524.23
• InChiKey: VPOUJZSSBSVPAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1',8,8'-tetrachloro-9,9'-bianthracene-10,10'(9H,9'H)-dione 在 盐酸 、 tin 、 溶剂黄146 作用下， 生成 4,5-dichloro-10H-anthracen-9-one
  参考文献：
  名称：

  Barnett; Cook; Matthews, Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 79

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 丙酮 、 calcium carbonate 作用下， 生成 1,1',8,8'-tetrachloro-9,9'-bianthracene-10,10'(9H,9'H)-dione
  参考文献：
  名称：

  Barnett; Cook; Matthews, Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 79

  摘要：

  DOI：

文献信息

• Theoretical Study and X-ray Determination of Bianthrones:  Long C−C Bond Length and Preferred Gauche Conformation
  作者：Pai-Chi Li、Tsung-Shing Wang、Gen-Hsian Lee、Yi-Hong Liu、Yu Wang、Chao-Tsen Chen、Ito Chao

  DOI：10.1021/jo020196g

  日期：2002.11.1

  A), nonplanarity of the anthracenone moiety (>20 degrees ), and preferred gauche conformation. However, when the gauche preference is weak, environmental effects such as solvation and packing forces can reverse it. As the degree of nonplanarity of the anthracenone moiety is consistently larger in the anti conformation than in the gauche and the ease of achieving nonplanarity is determined by flexibility

  联蒽醌（1，2b-5b）的五个X射线晶体学结构显示存在长的中心C（sp3）-C（sp3）键（>或= 1.60 A），且主要为gauche构象。进行了DFT计算，以研究联苯乙酰和相关模型分子的结构特征[更正]。我们的B3LYP / 6-31G气相计算结果表明，空间效应在导致较长的CC sigma键长（> 1.60 A），蒽酮部分的非平面性（> 20度）和优选的gauche构象中起作用。但是，当薄纱的偏爱性很弱时，诸如溶剂化和堆积力之类的环境影响会逆转它。
• ——
  作者：V. A. Loskutov

  DOI：10.1023/a:1012478517072

  日期：——

  The reaction of anthrone with thionyl chloride in benzene yields 10-(chlorosulfinyl)anthrone, while in DMF monothioanthraquinone S-oxide is formed; 4-substituted anthrones react with thionyl chloride in DMF in a similar way. The reaction of 4,5-dichloroanthrone with thionyl chloride results in dimerization or the substrate and formation of the corresponding bianthracenedione.
• Barnett; Goodway, Journal of the Chemical Society, 1930, p. 1348,1351
  作者：Barnett、Goodway

  DOI：——

  日期：——
• Synthesis and biological evaluation of novel 10-benzyl-substituted 4,5-dichloro-10H-anthracen-9-ones as inhibitors of keratinocyte hyperproliferation
  作者：Ulrich Kratz、Helge Prinz、Klaus Müller

  DOI：10.1016/j.ejmech.2010.08.047

  日期：2010.11

  A series of 10-substituted 4,5-dichloro-10H-anthracen-9-ones were synthesized in the search for novel agents against keratinocyte hyperproliferation. The antiproliferative activity of these novel anthrones was evaluated using the human keratinocyte line HaCaT as the primary test system. Structure-activity relationships with respect to the nature and position of the substituents at the benzyl moiety were studied, with a 3-hydroxy-4-methoxy-substitution pattern being the most potent (IC50 = 0.7 mu M) and comparable to the potency of the antipsoriatic anthralin. In contrast to anthralin, inhibition of keratinocyte hyperproliferation was not mediated by damage to the keratinocyte membrane, as the activity of lactate dehydrogenase released from the cytoplasm was in the control range. These findings may be rationalized as a benefit of the ineffectiveness of the novel anthrones to interact with the free radical 2, 2-diphenyl-1-picrylhydrazyl. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Barnett; Cook; Matthews, Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 79
  作者：Barnett、Cook、Matthews

  DOI：——

  日期：——