芘-2-羧酸甲酯 | 36373-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 芘-2-羧酸甲酯
• 英文名称: pyrene-2-carboxylic acid methyl ester
• 英文别名: 2-pyrenecarboxylic acid methyl ester；Pyren-2-carbonsaeure-methylester；2-Methoxycarbonyl-pyren；2-Pyrenecarboxylic acid,methylester；methyl pyrene-2-carboxylate
• CAS: 36373-11-2
• 化学式: C₁₈H₁₂O₂
• 分子量: 260.292
• InChiKey: WELQCEAIQITIFR-UHFFFAOYSA-N

物化性质

• 沸点：
  436.9±14.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  芘-2-羧酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide lithium aluminium tetrahydride 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 硝基苯 为溶剂， 反应 29.0h， 生成 (6,8-bis((4-(tert-butyl)phenyl)ethynyl)pyren-2-yl)methanol
  参考文献：
  名称：

  在空间受限的im二聚体中分子内准分子的形成和荧光延迟。

  摘要：

  描述了一系列包含五个通过1，3-二取代的亚苯基间隔基共价连接的pyr基末端的分子二元化合物的合成。units单元之间的空间连通程度是由每个pyr单元的6,8-位上连接的庞大部分所施加的空间相互作用调节的。对于对照化合物，仅氢原子占据6,8位（DP1），而其余化合物并入以三异丙基甲硅烷基（DP2），1-叔丁基苯（DP3），2,6-二叔-丁基苯（DP4）或1-叔丁基3,5-二甲基苯（DP5）单元。每种化合物在室温下在流体溶液中均显示出单体和准分子荧光的混合物，但在77 K的玻璃状基质中只有单体发射。单体与准分子荧光的比例明显取决于分子结构。DP1严重偏向于准分子，而DP4则富含单体荧光。报告了每种化合物的光物理性质，包括激光诱导的和延迟的荧光数据。分子内和双分子步骤都发生延迟荧光，但是这些事件发生在不同的时间尺度上。使用分子内三重态-三重态an灭作为分子成像手段的可能性增加了。但是这些事件发生

  DOI：

  10.1002/chem.200601498
• 作为产物：
  描述：

  甲醇 、 2-pyrenecarboxaldehyde 在 α,α,α-三联吡啶 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 sodium hydroxide 作用下， 反应 12.0h， 以96%的产率得到芘-2-羧酸甲酯
  参考文献：
  名称：

  使用二聚铑 (ii) 催化剂对醛和醇进行化学选择性脱氢酯化†

  摘要：

  已经使用 Rh-三联吡啶催化剂开发了醛与醇的脱氢交叉偶联以及伯醇的脱氢交叉偶联以生产酯。该催化剂表现出广泛的底物范围和良好的官能团耐受性，可高度选择性地提供酯。该催化剂的高化学选择性源于其对苄醇脱氢的偏好优于脂肪醇。初步机理研究表明，活性催化剂是二聚 Rh( II ) 物种，通过涉及金属-基础-金属协同作用的机制进行操作。

  DOI：

  10.1039/c6sc00145a

文献信息

• Vollmann et al., Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,137
  作者：Vollmann et al.

  DOI：——

  日期：——
• Flammang,R.; Martin,R.H., Bulletin des Societes Chimiques Belges, 1971, vol. 80, p. 433 - 438
  作者：Flammang,R.、Martin,R.H.

  DOI：——

  日期：——
• Efficient oxidation of promutagenic hydroxymethylpyrenes by cDNA-expressed human alcohol dehydrogenase ADH2 and its inhibition by various agents
  作者：Ronny Kollock、Walter Meinl、Heiko Schneider、Monika Batke、Heinz Frank、Albrecht Seidel、Hansruedi Glatt

  DOI：10.1016/j.bcp.2007.08.030

  日期：2008.1

  Alkylated polycyclic aromatic hydrocarbons can be metabolically activated via benzylic hydroxylation and sulphation to electrophilically reactive esters. However, we previously found that the predominant biotransformation route for the hepatocarcinogen 1-hydro-xymethylpyrene (1-HMP) in the rat in vivo is the oxidation of the side chain by alcohol dehydrogenases (ADHs) and aldehyde dehydrogenases to the carboxylic acid. Inhibition of this pathway by ethanol (competing ADH substrate) or 4-methylpyrazole (ADH inhibitor) led to a dramatic increase in the 1-HMP-induced DNA adduct formation in rat tissues in the preceding study. In order to elucidate the role of individual ADHs in the metabolism of alkylated polycyclic aromatic hydrocarbons, we expressed the various members of the human ADH family in bacteria. Cytosolic preparations from bacteria expressing ADH2 clearly oxidized hydroxymethylpyrene isomers (1-, 2- and 4-HMP) with the highest rate. This form was purified to near homogeneity to perform detailed kinetic analyses. High catalytic efficiencies (V-max/K-m) were observed with HMPs. Thus, this value was 10,000-fold higher for 2-HMP than for the reference substrate, ethanol. The corresponding aldehydes were also efficiently reduced by ADH2. 4-Methylpyrazole inhibited the oxidation of the HMP isomers as well as the reverse reaction. Daidzein, cimetidine and the competing substrate ethanol were further compounds that inhibited the ADH2-mediated oxidative detoxification of 1-HMP. (c) 2007 Elsevier Inc. All rights reserved.
• Gerasimenko,Yu.E.; Poteleshchenko,V.P., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 1084 - 1087
  作者：Gerasimenko,Yu.E.、Poteleshchenko,V.P.

  DOI：——

  日期：——
• Sorption of Polycyclic Aromatic Compounds to Humic Acid As Studied by High-Performance Liquid Chromatography
  作者：Torben Nielsen、Katrin Siigur、Christian Helweg、Ole Jørgensen、Poul Erik Hansen、Uuve Kirso

  DOI：10.1021/es960620t

  日期：1997.4.1

  Aldrich humic acid was chemically immobilized to the silanol surface of a column material to be used for highperformance liquid chromatography (HPLC). The retention factors to the humic acid column material of 45 polycyclic aromatics compounds (PAC) were determined by HPLC. The PAC include PAH, N-, S-, O-PAC and substituted PAC (9-substituted anthracenes, bromopyrenes, and quinoline derivatives). The sorption coefficient of quinoline to humic acid was directly determined at different pH. The good correlation achieved between the HPLC retention factors and literature K-oc values, including the presented one of quinoline, was applied to determine K-oc of 39 other PAC. The determined K-oc values were parametrized with regard to size, ring heteroatoms, and steric and substituent effects and were compared with literature values of water solubility and recently determined octanol-water partition coefficients. It is shown that the sorption of PAC to humic a cid is not only affected by hydrophobic interactions but also by hydrogen and especially ionic bonds. The investigation shows that the application of humic acid stationary HPLC phases is a valuable supplement to other techniques for determination of K-oc.