3-Ethynylphenanthrene | 32870-97-6

• 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: 3-Ethynylphenanthrene
• CAS: 32870-97-6
• 化学式: C₁₆H₁₀
• 分子量: 202.255
• InChiKey: LOGSUFFLSMEOEC-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  377.7±11.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-Ethynylphenanthrene 在 氧气 、 氯化铵 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3,3'-Diphenanthrylpentaacetylen
  参考文献：
  名称：

  带有芳香族端子组的线性共轭系统。V. 2,2'-、3,3'-和9,9'-二菲基聚炔的合成和电子光谱

  摘要：

  合成了 2,2'-、3,3'- 和 9,9'-二菲基多炔（Vn、VIn 和 VIIn，n=1-6）并测量了它们的电子光谱。发现各系列二菲基聚炔（Vn、VIn 和 VIIn）的光谱中最长波长吸收最大值（λmax）随炔键数（n）的 x 次方线性移动，[λmax∝ nx]，对于 Vn，x=1.3，对于 VIn 和 VIIn，x=1.4。

  DOI：

  10.1246/bcsj.44.2237
• 作为产物：
  描述：

  3-乙酰基菲 生成 3-Ethynylphenanthrene
  参考文献：
  名称：

  带有芳香族端子组的线性共轭系统。V. 2,2'-、3,3'-和9,9'-二菲基聚炔的合成和电子光谱

  摘要：

  合成了 2,2'-、3,3'- 和 9,9'-二菲基多炔（Vn、VIn 和 VIIn，n=1-6）并测量了它们的电子光谱。发现各系列二菲基聚炔（Vn、VIn 和 VIIn）的光谱中最长波长吸收最大值（λmax）随炔键数（n）的 x 次方线性移动，[λmax∝ nx]，对于 Vn，x=1.3，对于 VIn 和 VIIn，x=1.4。

  DOI：

  10.1246/bcsj.44.2237

文献信息

• Synthesis of Luminescent 2-7 Disubstituted Silafluorenes with alkynyl-carbazole, -phenanthrene, and -benzaldehyde substituents
  作者：Stephan Germann、Shelby J. Jarrett、Cynthia M. Dupureur、Nigam P. Rath、Ethan Gallaher、Janet Braddock-Wilking

  DOI：10.1016/j.jorganchem.2020.121514

  日期：2020.11

  Three new fluorescent 2,7-alkynyl(aryl)-3,6-dimethoxy-9,9-diphenylsilafluorenes have been synthesized using a Pd-catalyzed Sonogashira coupling reaction to incorporate alkynyl(aryl) groups at the 2,7-positions of the ring. The substituents include 9-ethynylcarbazole, 4-ethynylbenzaldehyde, and 3-ethynylphenanthrene. These new compounds were characterized utilizing X-ray crystallography as well as multinuclear NMR, mass spectrometry, UV-Vis, and fluorescence spectroscopic techniques. These silafluorenes, which are yellow crystals in the solid state, showed high quantum yields with moderate molar extinction coefficients in dichloromethane and strong blue emission. Key words: silafluorene, luminescence. (c) 2020 Elsevier B.V. All rights reserved.
• Origin of Pyrene under High Temperature Conditions in the Gas Phase. The Pivotal Role of Phenanthrene
  作者：Martin Sarobe、Leonardus W. Jenneskens、Ralph G. B. Steggink、Tom Visser

  DOI：10.1021/jo982030e

  日期：1999.5.1

  4-Ethynylphenanthrene (15), and the latent precursors for 2-ethynyl- (18) and 3-ethynylphenanthrene (19), viz., 2-(1-chloroethenyl)- (16) and 3-(1-chloroethenyl)phenanthrene (17), respectively, have been subjected to flash vacuum thermolysis (FVT). Whereas at 800 degrees C 15 is quantitatively converted into pyrene (1), 16 and 17 only give 18 and 19, respectively. Both 18 and 19 contain redundant ethynyl substituents, i.e., after ethynyl-ethylidene carbene equilibration neither five- nor six-membered ring formation can occur by carbene C-H insertion. At T greater than or equal to 1000 degrees C 16 and 17 gave pyrolysates containing the same set of 11 (non)-alternant polycyclic aromatic hydrocarbons (PAH), albeit in a different ratio. The different product ratio suggests that redundant ethynyl substituents migrate along the phenanthrene periphery presumably via transient cyclobuta-PAH intermediates toward positions suitable for either five- or six-membered ring formation by carbene C-H insertion. The results provide an explanation for the ubiquitous formation of pyrene (1), acephenanthrylene (9), and fluoranthene (3) during (incomplete) combustion. Phenanthrene (2) appears to be a point of divergence in PAH growth by C-2 addition.
• Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair
  作者：Subhendu Sekhar Bag、Sangita Talukdar、Katsuhiko Matsumoto、Rajen Kundu

  DOI：10.1021/jo302033f

  日期：2013.1.18

  We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible pi-pi stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.
• Linear Conjugated Systems Bearing Aromatic Terminal Groups. V. Syntheses and Electronic Spectra of 2,2′-, 3,3′-, and 9,9′-Diphenanthrylpoly-ynes
  作者：Shuzo Akiyama、Masazumi Nakagawa

  DOI：10.1246/bcsj.44.2237

  日期：1971.8

  2,2′-, 3,3′-, and 9,9′-Diphenanthrylpoly-ynes (Vn, VIn, and VIIn, n=1–6) were synthesized and their electronic spectra were measured. It was found that the longest-wavelength absorption maxima (λmax) in the spectra of each series of the diphenanthrylpoly-ynes (Vn, VIn and VIIn) shift linearly with the xth power of the number of acetylenic bond (n), [λmax∝nx], being x=1.3 for Vn and x=1.4 for VIn and

  合成了 2,2'-、3,3'- 和 9,9'-二菲基多炔（Vn、VIn 和 VIIn，n=1-6）并测量了它们的电子光谱。发现各系列二菲基聚炔（Vn、VIn 和 VIIn）的光谱中最长波长吸收最大值（λmax）随炔键数（n）的 x 次方线性移动，[λmax∝ nx]，对于 Vn，x=1.3，对于 VIn 和 VIIn，x=1.4。
• Aryl Acetylenes as Mechanism-Based Inhibitors of Cytochrome P450-Dependent Monooxygenase Enzymes
  作者：Maryam Foroozesh、Ginny Primrose、Zuyu Guo、L. Chastine Bell、William L. Alworth、F. Peter Guengerich

  DOI：10.1021/tx960064g

  日期：1997.1.1

  methylene groups are selective inhibitors of P450 2B1/2B2 in liver microsomes from rats. Aryl acetylenes also act as suicide inhibitors of P450 1A2 in human liver microsomes, of purified P450 1A2 from rabbit or rat liver in reconstituted systems, and of purified recombinant human P450 1A2 and 1A1 in reconstituted systems. 4-(1-Propynyl)biphenyl (4PBi) inactivated P450 1A2-dependent ethoxyresourfin deethylation

  已经研究了芳基乙炔在从暴露于β-萘黄酮，异黄酮或苯巴比妥的大鼠制备的肝微粒体中作为细胞色素P450（P450）依赖性烷氧基间苯二酚脱烷基化脱烷基活性的抑制剂。研究的许多乙炔会产生假一阶时间依赖性和NADPH依赖性的脱烷基活性损失，这些是基于机制的不可逆失活（自杀抑制）的特征。用甲基取代芳基乙炔的末端氢以将乙炔转化为丙炔，可以增强对P450 1A酶的抑制作用。在某些情况下，这种修饰将可逆的P450抑制剂转化为自杀抑制剂。相反，乙炔比相应的丙炔更有效地抑制P450 2B依赖性脱烷基的自杀。在大鼠肝微粒体内，在萘2位或菲9位上具有乙炔基的芳基乙炔和具有2、3或4个亚甲基烷基链的芳基烷基乙炔是P450 2B1 / 2B2的选择性抑制剂。芳基乙炔还充当人肝微粒体中P450 1A2的自杀抑制剂，重组系统中来自兔或大鼠肝脏的纯化P450 1A2的自杀抑制剂以及重组系统中纯化的重组人P450 1A2和1A