1,2,3,4-四氢屈-1-酮 | 63642-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 1,2,3,4-四氢屈-1-酮
• 英文名称: 1,2,3,4-tetrahydrochrysen-1-one
• 英文别名: 1-Keto-1,2,3,4-tetrahydrochrysen；3,4-dihydro-2H-chrysen-1-one；3,4-Dihydro-2H-chrysen-1-on；1(2H)-Chrysenone, 3,4-dihydro-；3,4-dihydro-2H-chrysen-1-one
• CAS: 63642-50-2
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: ZVYZDXRSPQXUIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,2,3,4-四氢屈-1-酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium methylate 、 dinitrogen tetraoxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 8.67h， 生成 3,4-dihydro-6-nitrochrysene
  参考文献：
  名称：

  Synthesis of anti-1,2-Dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene and Its Reaction with 2‘-Deoxyguanosine- 5‘-Monophosphate, 2‘-Deoxyadenosine-5‘-Monophosphate, and Calf Thymus DNA in Vitro

  摘要：

  The remarkable carcinogenic activity of 6-nitrochrysene (6-NC) in several animal models, and its environmental presence, suggest its potential importance with regard to human cancer development. Depending on the bioassay model, 6-NC can be activated by simple nitro reduction, ring oxidation, or by a combination of ring oxidation and nitro reduction. Only the first pathway has been clearly established. Thus, this study purports to unequivocally define the other pathways. Toward this end, we report for the first time the synthesis of anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene (6-NCDE), a likely ultimate carcinogenic metabolite of 6-NC. Also, we describe our initial investigation of its binding with calf thymus DNA, 2'-deoxyguanosine-5'-monophosphate (2'-dGuo), and 2'-deoxyadenosine-5'-monophosphate (2'-dAdo) in vitro. These adduct markers were then employed for comparison with those obtained in the rat after in vivo treatment with 6-NC. On the basis of the results, it appears that the major adduct formed in the liver of rats treated with 6-NC is not derived from 6-NCDE.

  DOI：

  10.1021/tx000104n
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氟酸 作用下， 生成 1,2,3,4-四氢屈-1-酮
  参考文献：
  名称：

  76.多环芳烃。XXX部分。甲酚的合成

  摘要：

  DOI：

  10.1039/jr9450000288

文献信息

• Hoch, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1938, vol. 207, p. 921
  作者：Hoch

  DOI：——

  日期：——
• The constituents of high-boiling petroleum distillates. Part I. Preliminary studies
  作者：W. Carruthers、J. W. Cook

  DOI：10.1039/jr9540002047

  日期：——
• THE SYNTHESIS OF METHYLCHRYSENES AND RELATED COMPOUNDS¹
  作者：W. E. BACHMANN、W. S. STRUVE

  DOI：10.1021/jo01210a009

  日期：1940.7
• The Synthesis of Compounds Related to the Sex Hormones
  作者：W. E. Bachmann、R. A. Gregg、E. F. Pratt

  DOI：10.1021/ja01252a019

  日期：1943.12
• 532. Studies in polycyclic systems. Part I. A new synthesis of picene
  作者：D. Nasipuri

  DOI：10.1039/jr9580002618

  日期：——