4H-Cyclopentachrysen-4-one | 86853-91-0

• 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-Cyclopentachrysen-4-one
• 英文别名: cyclopentachrysene-4-one；10(H)-oxo-10,11-methanochrysene；10(H)oxo-10, 11-methanochrysene；4H-cyclopenta(def)chrysen-4-one；Cyclopenta[def]chrysene-4-one；Starbld0027436；pentacyclo[14.2.1.03,8.09,18.012,17]nonadeca-1,3,5,7,9(18),10,12(17),13,15-nonaen-19-one
• CAS: 86853-91-0
• 化学式: C₁₉H₁₀O
• 分子量: 254.288
• InChiKey: GEMOJIKPQLZCMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4H-Cyclopentachrysen-4-one 在 肼 作用下， 以 二乙二醇 为溶剂， 反应 2.0h， 生成 Cyclopenta[def]chrysen-(4E)-ylidene-hydrazine
  参考文献：
  名称：

  SYNTHESIS OF 4H-CYCLOPENTA[def]CHRYSENE AND OTHER METHYLENE-BRIDGED POLYCYCLIC HYDROCARBONS

  摘要：

  DOI：

  10.1080/00304949709355210
• 作为产物：
  描述：

  Chrysene-11-carboxylic acid 在 氢氟酸 作用下， 以65%的产率得到4H-Cyclopentachrysen-4-one
  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

• Study of Photochemistry without Light of Substituted Benzylidine Acenaphthenones
  作者：VIJENDER GOEL

  DOI：10.13005/ojc/290148

  日期：2013.3.5

  In order to draw a parallel between light induced reactions as well as photochemistry without light (chemiluminescence), the substituted benzylidineacenaphthenones were subjected to dioxetanedione reactions, which are formed in situ by the reaction of 2,4-dimitrophenyloxalate with hydrogen peroxide to provide chrysene derivatives as well as naphthalene 1,8-dicarboxylic acid anhydride and benzoic acid

  为了在光诱导的反应和无光的光化学反应之间产生相似性（化学发光），对取代的苄基ac烯酮进行二氧杂环丁酮反应，该反应是由2,4-二亚硝基苯草酸酯与过氧化氢反应原位形成的，以提供芴衍生物以及萘1,8-二羧酸酐和苯甲酸，其结构由IR和1 H NMR光谱确定。
• 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.
• Parshad; Sharma, Journal of the Indian Chemical Society, 1989, vol. 66, # 2, p. 106 - 109
  作者：Parshad、Sharma

  DOI：——

  日期：——
• Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation
  作者：Juan J. González、Nuria García、Berta Gómez-Lor、Antonio M. Echavarren

  DOI：10.1021/jo962059n

  日期：1997.3.1

  The palladium-catalyzed intramolecular arylation reaction has been applied to the synthesis of the spiro polycyclic aromatic hydrocarbons and planar polycyclic aromatic hydrocarbons by formation of a six-membered ring. The reaction proceeds more readily with aryl bromides substituted with electron-withdrawing groups by using palladium acetate in N,N-dimethylformamide as the solvent. For the less reactive-p-methoxyaryl derivatives the use of LiI as an additive was shown to give the best results. The results obtained in the cyclization of nitro derivatives 21 and 23 suggest that the second step of the cyclization reaction is not an electrophilic substitution reaction.
• LEE-RUFF, E.;KRUK, H.;KATZ, M., J. ORG. CHEM., 1984, 49, N 3, 553-555
  作者：LEE-RUFF, E.、KRUK, H.、KATZ, M.

  DOI：——

  日期：——