6-甲基苯并[a]芘 | 2381-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 6-甲基苯并[a]芘
• 英文名称: 6-Methylbenzopyrene
• 英文别名: 6-methyl-benzo[def]chrysene；6-Methyl-benzo[def]chrysen；6-methyl-benzo[a]pyrene；6-Methyl-¹³C-benzopyren；6-Methylbenzo--pyren；6-Methyl-benzopyren；6-Methylbenzo[a]pyrene
• CAS: 2381-39-7
• 化学式: C₂₁H₁₄
• 分子量: 266.342
• InChiKey: YFYHJNJCAGHSFA-UHFFFAOYSA-N

物化性质

• 熔点：
  171.25°C
• 沸点：
  509.54°C (rough estimate)
• 密度：
  1.1340 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.047
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

SDS

反应信息

• 作为反应物：
  描述：

  6-甲基苯并[a]芘 在 碘 、 silver perchlorate 、 sodium acetate 作用下， 以 苯 、 水 、 乙腈 为溶剂， 以5%的产率得到苯并[b]芘-6-基甲醇
  参考文献：
  名称：

  苯并[a] py和6-取代衍生物的自由基阳离子：与亲核试剂和DNA反应。

  摘要：

  1.在AgClO4在苯中的存在下，I2氧化苯并[a] py（BP），生成BP。+ ClO4-.AgI复合物。使用相同的方法由6-FBP，6-ClBP，6-BrBP和6-CH3BP产生自由基阳离子。2.BP，6-FBP，6-ClBP和6-BrBP自由基阳离子高氯酸盐与H 2 O反应生成BP 1,6-，3,6-和6,12-二酮，而6-CH3BP。+ ClO4-。 AgI产生6-CH 2 OHBP。3.当BP。+ ClO4-.AgI和6-FBP。+ ClO4-.AgI与NaOAc在H2O / CH3CN（9：1）中反应时，除醌外，还形成了6-OAcBP。在6-ClBP。+ ClO4-.AgI的情况下，除了二酮以外，还形成少量的1-OAc-6-ClBP和3-OAc-6-ClBP，而对于6-BrBP和6-CH3BP反应产物分别为BP二酮和6-CH 2 OHBP。4.这些结果证实了电荷在BP。+中位于

  DOI：

  10.3109/00498259509061890
• 作为产物：
  描述：

  6-甲酰基苯并(a)芘 在 氢氧化钾 、 一水合肼 作用下， 生成 6-甲基苯并[a]芘
  参考文献：
  名称：

  6-取代苯并[ a ] py衍生物的合成与性能

  摘要：

  描述了制备苯并[ a ] py-6-甲醛的改进方法，讨论了该物质中杂质的性质，描述了从甲醛合成许多6-取代的苯并[ a ] py衍生物的方法，研究了N-卤代琥珀酰亚胺在制备苯并[ a ] py的6-卤代衍生物中的用途。描述了衍生物的荧光光谱和tlc行为。

  DOI：

  10.1039/p19720000710

文献信息

• One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate. A model for metabolic activation
  作者：Paolo Cremonesi、Ercole L. Cavalieri、Eleanor G. Rogan

  DOI：10.1021/jo00276a013

  日期：1989.7
• Radical Cations of Benzo[a]pyrene and 6-Substituted Derivatives: Synthesis and Reaction with Nucleophiles
  作者：Paolo Cremonesi、Douglas E. Stack、Eleanor G. Rogan、Ercole L. Cavalieri

  DOI：10.1021/jo00104a024

  日期：1994.12

  Radical cations of benzo[a]pyrene (BP) and 6-substituted derivatives were synthesized by two methods: reaction of the hydrocarbon with I-2 and AgClO4 in benzene, and reaction of the hydrocarbon with NOBF4 in CH3CN/CH2Cl2. Both the radical cation perchlorates and tetrafluoroborates were stable for prolonged periods of time when stored under argon at subzero temperatures. The radical cations were reacted with nucleophiles of various strengths, namely H2O, AcO- and F-, as a means of best characterizing these intermediates, as well as determining their chemical properties. Reaction of BP, 6-FBP, 6-ClBP, and 6-BrBP radical cation perchlorates with H2O produced BP 1,6- 3,6-, and 6,12-dione, whereas the radical cation derived from 6-CH3BP yielded 6-CH2OHBP. When (BPClO4-)-Cl-.+ and 6-(FBPClO4-)-Cl-.+ were reacted with NaOAc in H2O/CH3CN (9:1), 6-OAcBP was formed, in addition to the quinones. 6-(ClBPClO4-)-Cl-.+ formed a small amount of 1-OAc-6-ClBP and 3-OAc-6-ClBP, in addition to the diones, whereas for 6-(BrBPClO4-)-Cl-.+ and 6-(CH3BPClO4-)-Cl-.+ the reaction products were BP diones and 6-CH2OHBP, respectively. Reactions conducted under anhydrous conditions, using tetramethylammonium acetate in CH3CN, gave similar results, except that no quinones were formed. These results confirm the reactivity of nucleophiles at the positions of high charge localization in the BP.+, i.e. C-6, followed by C-1 and C-3.
• Uibopuu, Kh. M.; Gubergritis, M. Ya.; Perin-Roussel, O., Journal of applied chemistry of the USSR, 1982, vol. 55, # 11, p. 2277 - 2285
  作者：Uibopuu, Kh. M.、Gubergritis, M. Ya.、Perin-Roussel, O.、Perin, F.、Jacquignon, P. S.

  DOI：——

  日期：——
• The Oxidation of Methylcholanthrene and 3,4-Benzpyrene with Lead Tetraacetate; Further Derivatives of 3,4-Benzpyrene
  作者：Louis F. Fieser、E. B. Hershberg

  DOI：10.1021/ja01277a077

  日期：1938.10
• Uibopuu, Kh. M.; Kirso, U. E., Journal of applied chemistry of the USSR, 1982, vol. 55, # 1, p. 160 - 162
  作者：Uibopuu, Kh. M.、Kirso, U. E.

  DOI：——

  日期：——