4H-Fluoreno<4,4a,4b,5-abc>anthracen-4-ol | 143924-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4H-Fluoreno<4,4a,4b,5-abc>anthracen-4-ol
• 英文别名: Hexacyclo[18.2.1.05,22.06,15.08,13.016,21]tricosa-1,3,5(22),6,8,10,12,14,16(21),17,19-undecaen-23-ol
• CAS: 143924-56-5
• 化学式: C₂₃H₁₄O
• 分子量: 306.364
• InChiKey: OBYUFGLVQFUUJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4H-Benzocyclopentatriphenylene 生成 4H-Fluoreno<4,4a,4b,5-abc>anthracen-4-ol
  参考文献：
  名称：

  Synthesis of ketone and alcohol derivatives of methylene-bridged polyarenes, potentially new classes of active metabolites of carcinogenic hydrocarbons

  摘要：

  Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described. The polyarenes investigated include 4H-cyclopenta[def]phenanthrene (1a), fluorene (2a), 7H-benzo[c]fluorene (3a), 4H-cyclopenta[def]chrysene (4a), 11H-Benz[bc]aceanthrylene (5a), 10H-indeno[1,2,7,7a-bcd]pyrene (6a), 11H-dibenzo[bc,l]aceanthrylene (7a), 4H-fluoreno[4,4a,4b,5-abc]anthracene (8a), and 7H-dibenzo[a,g]fluorene (9a). The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediates with molecular oxygen. The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions With O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group. Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone lb. The related bridge alcohols am readily obtained in yields of 75-95% by reduction of the crude products from the preceding oxidations with NaBH4.

  DOI：

  10.1021/jo00049a045

文献信息

• Synthesis of ketone and alcohol derivatives of methylene-bridged polyarenes, potentially new classes of active metabolites of carcinogenic hydrocarbons
  作者：Ronald G. Harvey、Elias Abu-Shqara、Cheng Xi Yang

  DOI：10.1021/jo00049a045

  日期：1992.11

  Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described. The polyarenes investigated include 4H-cyclopenta[def]phenanthrene (1a), fluorene (2a), 7H-benzo[c]fluorene (3a), 4H-cyclopenta[def]chrysene (4a), 11H-Benz[bc]aceanthrylene (5a), 10H-indeno[1,2,7,7a-bcd]pyrene (6a), 11H-dibenzo[bc,l]aceanthrylene (7a), 4H-fluoreno[4,4a,4b,5-abc]anthracene (8a), and 7H-dibenzo[a,g]fluorene (9a). The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediates with molecular oxygen. The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions With O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group. Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone lb. The related bridge alcohols am readily obtained in yields of 75-95% by reduction of the crude products from the preceding oxidations with NaBH4.