4H-cyclopentachrysene | 202-98-2

• 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-cyclopentachrysene
• 英文别名: cyclpentachrysene；4H-cyclopenta[def]chrysene；4,5-Methanochrysene；4H-cyclopenta[def]chrysene；4H-Cyclopenta[def]chrysen；4H-Cyclopenta(def)chrysene；pentacyclo[14.2.1.03,8.09,18.012,17]nonadeca-1,3,5,7,9(18),10,12(17),13,15-nonaene
• CAS: 202-98-2
• 化学式: C₁₉H₁₂
• 分子量: 240.304
• InChiKey: GTDQLJVKXFXBMM-UHFFFAOYSA-N

物化性质

• 熔点：
  175°C
• 沸点：
  318.02°C (rough estimate)
• 密度：
  1.1385 (estimate)
• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）
• 保留指数：
  418.4

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• 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

ADMET

毒理性

• 致癌物分类

国际癌症研究机构致癌物：4H-环戊二烯[def]屈艹苯

IARC Carcinogenic Agent:4H-Cyclopenta[def]chrysene

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论：第92卷：（2010年）一些非杂环多环芳烃及其相关暴露

IARC Monographs:Volume 92: (2010) Some Non-heterocyclic Polycyclic Aromatic Hydrocarbons and Some Related Exposures

来源:International Agency for Research on Cancer (IARC)

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  4H-cyclopentachrysene 在 chromium(VI) oxide 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到4H-Cyclopentachrysen-4-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：

  Chrysene-11-carboxylic acid 在 氢氧化钾 、 氢氟酸 、 一水合肼 作用下， 以 乙二醇 为溶剂， 反应 1.0h， 生成 4H-cyclopentachrysene
  参考文献：
  名称：

  A short synthesis of 4,5-methanochrysene and 6-oxo-7-oxabenzo[a]pyrene, two benzo[a]pyrene analogs

  摘要：

  DOI：

  10.1021/jo00177a035

文献信息

• A new general synthesis of polycyclic aromatic compounds based on enamine chemistry
  作者：Ronald G. Harvey、John Pataki、Cecilia Cortez、Pasquale Di Raddo、Cheng Xi Yang

  DOI：10.1021/jo00003a050

  日期：1991.2

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.
• Synthesis of alkyl-substituted benzo[c]phenanthrenes and chrysenes by photocyclization
  作者：Donald L. Nagel、Robert Kupper、Kenneth Antonson、Lawrence Wallcave

  DOI：10.1021/jo00442a041

  日期：1977.10
• Electrophilic substitution of methylene-bridged polycyclic aromatic hydrocarbons
  作者：Elias Abu-Shqara、Cheng Xi Yang、Ronald G. Harvey

  DOI：10.1021/jo00038a016

  日期：1992.6

  The electrophilic bromination and formylation of the methylene-bridged polycyclic aromatic hydrocarbons 11H-benz[bc]aceanthrylene (2), 4H-cyclopenta[def]chrysene (3), 13H-dibenz[bc,l]aceanthrylene (4), and 4H-benzo[b]cyclopenta[mno]chrysene (5) were investigated. All reactions proceeded with high regioselectivity to afford predominantly a single major isomeric product. The sole exception was bromination of 3 which gave a small amount of a second isomeric product. The sites of electrophilic substitution were correlated with theoretical predictions from semiempirical molecular orbital calculations using the MNDO method, The observed sites of electrophilic substitution were in excellent agreement with the theoretical predictions in the cases of 2-4. However, in the case of 5, substitution took place in the 6-position, whereas the site predicted to be most reactive is the 5-position. In addition, the aryl aldehyde products were converted into the corresponding methyl derivatives for studies of their potential carcinogenicity.
• SYNTHESIS OF 4<i>H</i>-CYCLOPENTA[<i>def</i>]CHRYSENE AND OTHER METHYLENE-BRIDGED POLYCYCLIC HYDROCARBONS
  作者：Wei Dai、Ronald G. Harvey

  DOI：10.1080/00304949709355210

  日期：1997.6
• Stable Ion Studies of the Chrysene Skeleton. Protonation of Chrysene, 6-Halochrysenes, 6-Acetylchrysene, and 4<i>H</i>-Cyclopenta[<i>def</i>]chrysene:  NMR Studies of Charge Distribution in Chrysenium Cations and AM1 Calculations
  作者：Kenneth K. Laali、Sandro Hollenstein、Ronald G. Harvey、Poul Erik Hansen

  DOI：10.1021/jo9620730

  日期：1997.6.13

  Chrysene (1), 6-fluorochrysene (2), 6-chlorochrysene (3), and 6-bromochrysene (4) are cleanly monoprotonated in FSO3H . SbF5 (ca. 10:1)/SO2ClF at the C-12 position. 6-Acetylchrysene (5) is CO-protonated in FSO3H/SO2ClF with significant charge delocalization into the chrysene and provides a model for a C-6-protonated chrysenium cation. 4H-Cyclopenta[def]chrysene (6) is protonated at C-5 (site of bromination and acetylation). The observed chrysenium (methanochrysenium) cations are those predicted by AM1 to have the lowest energies. The NMR characteristics of the resulting arenium ions are discussed and the he Delta delta Cs-13 are compared with AM1 calculated changes in charges [Delta q(c) = q(c)(ion) - q(c)(neutral)]. Possible relationships between the charge delocalization path in chrysenium ions and metabolic activation of chrysenes by electrophilic pathways via the bay-region epoxide ring opening (--> PAH-DNA adduct) are evaluated.