indeno<1,2,7,7a-bcd>pyrene | 59004-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: indeno<1,2,7,7a-bcd>pyrene
• 英文别名: 10H-Indeno<1,2,7,7a-bcd>pyrene；10H-Cyclopenta[mno]benzo[a]pyrene；hexacyclo[10.7.1.14,19.02,10.03,8.016,20]henicosa-1(19),2,4(21),5,7,10,12,14,16(20),17-decaene
• CAS: 59004-72-7
• 化学式: C₂₁H₁₂
• 分子量: 264.326
• InChiKey: WEKAXSAVALUHAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  indeno<1,2,7,7a-bcd>pyrene 在 正丁基锂 、 氧气 作用下， 生成 10H-Indeno<1,2,7,7a-bcd>pyren-10-one
  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
• 作为产物：
  描述：

  (4H-Cyclopenta[def]chrysen-9-yl)-acetaldehyde 在 甲烷磺酸 作用下， 生成 indeno<1,2,7,7a-bcd>pyrene
  参考文献：
  名称：

  亚甲基桥联苯并ren苯的合成，汽车尾气中的致癌成分

  摘要：

  描述了苯并[a] py和苯并[e] py的亚甲基桥衍生物的合成（1和2）。后者是通过在关键步骤中将a的二酸衍生物串联环化的途径获得的。尽管类似的制备1失败了，但它是通过基于环戊并[菲]菲的合成路线成功获得的。

  DOI：

  10.1016/s0040-4039(00)70629-0

文献信息

• YOUNG, ROBERT J.;HARVEY, RONALD G., TETRAHEDRON LETT., 30,(1989) N8, C. 6603-6606
  作者：YOUNG, ROBERT J.、HARVEY, RONALD G.

  DOI：——

  日期：——
• 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.
• Syntheses of methylene-bridged benzopyrenes, carcinogenic components of automobile exhaust residue
  作者：Robert J. Young、Ronald G. Harvey

  DOI：10.1016/s0040-4039(00)70629-0

  日期：——

  Syntheses of the methylene-bridged derivatives of benzo[a]pyrene and benzo[e]pyrene (1 and 2) are described. The latter was obtained by a route involving in the key step tandem cyclization of a diacid derivative of pyrene. Although analogous preparation of 1 failed, it was obtained successfully by a synthetic route based on cyclopenta[def]phenanthrene.

  描述了苯并[a] py和苯并[e] py的亚甲基桥衍生物的合成（1和2）。后者是通过在关键步骤中将a的二酸衍生物串联环化的途径获得的。尽管类似的制备1失败了，但它是通过基于环戊并[菲]菲的合成路线成功获得的。