2-乙炔基菲 | 32870-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 2-乙炔基菲
• 英文名称: 2-Ethynylphenanthrene
• CAS: 32870-96-5
• 化学式: C₁₆H₁₀
• 分子量: 202.255
• InChiKey: OEMQNFYGCFXEEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °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：

  2-乙炔基菲 在 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  金（I）对乙炔基菲的室温磷光的影响

  摘要：

  合成具有通式PR 3 - Au -C≡C-菲（PR 3 = PPh 3（1 a / 2 a），PMe 3（1 b / 2 b），PNaph的两个系列的金（I）配合物3（1 c / 2 c））或（diphos）（Au-C≡C-菲）2（diphos = 1,1-双（二苯基膦基）甲烷，dppm（1 d / 2 d），1,4-bis （二苯基膦基）丁烷，dppb（1 e / 2 e））已实现。两个系列中的发色团菲炔基取代基的位置不同，处于9-位（9- ethynylphenanthrene）为L1系列和在2-位（2- ethynylphenanthrene）为L2系列。对于化合物1a，1e，2a和2c，这些化合物已通过1 H，31 P NMR，IR光谱，质谱和单晶X射线衍射分辨率进行了充分表征。。在溶液中以及在不同极性的有机基质（聚甲基丙烯酸甲酯和Zonex）中，已经研究了未配位配体和相应配合物的

  DOI：

  10.1002/chem.202004051
• 作为产物：
  描述：

  2-溴菲 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 2-乙炔基菲
  参考文献：
  名称：

  金（I）对乙炔基菲的室温磷光的影响

  摘要：

  合成具有通式PR 3 - Au -C≡C-菲（PR 3 = PPh 3（1 a / 2 a），PMe 3（1 b / 2 b），PNaph的两个系列的金（I）配合物3（1 c / 2 c））或（diphos）（Au-C≡C-菲）2（diphos = 1,1-双（二苯基膦基）甲烷，dppm（1 d / 2 d），1,4-bis （二苯基膦基）丁烷，dppb（1 e / 2 e））已实现。两个系列中的发色团菲炔基取代基的位置不同，处于9-位（9- ethynylphenanthrene）为L1系列和在2-位（2- ethynylphenanthrene）为L2系列。对于化合物1a，1e，2a和2c，这些化合物已通过1 H，31 P NMR，IR光谱，质谱和单晶X射线衍射分辨率进行了充分表征。。在溶液中以及在不同极性的有机基质（聚甲基丙烯酸甲酯和Zonex）中，已经研究了未配位配体和相应配合物的

  DOI：

  10.1002/chem.202004051

文献信息

• 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
• 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.
• Synthesis and Properties of Si-Containing Poly(diarylacetylene)s and Their Desilylated Polymer Membranes
  作者：Toshikazu Sakaguchi、Masashi Shiotsuki、Toshio Masuda

  DOI：10.1021/ma035993a

  日期：2004.6.1

  The polymerization of 1-[(p-trimethylsilyl)phenyl]-2-(2-fluorenyl)acetylene (1c) with TaCl5-n-Bu4Sn produced a high molecular weight polymer (2c), whose M-w reached 3.4 x 10(6). 1-[(p-Trimethylsilyl)-phenyl]-2-(2-phenanthryl)acetylene (1d) and 1-[(p-trimethylsilyl)phenyl]-2-(4-biphenyl)acetylene (le) were also polymerized to give high molecular weight polymers (2d and 2e) in good yields. In contrast, the polymerization of 1-[(p-trimethylsilyl)phenyl]-2-(2-anthryl)acetylene (1f) provided no polymer probably owing to the steric reason. The formed polymers 2c and 2d were soluble in common solvents such as toluene and chloroform and afforded free-standing membranes by casting from toluene solution. The onset temperatures of weight loss of polymers 2c and 2d in air were about 430 degreesC, indicating very high thermal stability. The membranes of 2c and 2d obtained by the casting method showed high gas permeability; e.g., their oxygen permeability coefficients (Po-2) were 1650 and 460 barrers, respectively. The membranes of 2c and 2d were desilylated with trifluoroacetic acid to provide the membranes of poly [1-phenyl-2-(2-fluorenyl)acetylene] (3c) and poly[1-phenyl-2-(2-phenanthryl)acetylene] (3d). The desilylated poly(diarylacetylene)s exhibited even higher Po-2 values of 2150 and 1300 barrers, respectively. These desilylated polymers were insoluble in any solvents and showed higher thermal stability than those of 2c and 2d.
• Synthesis and characterization of unsymmetrical phenylene–ethynylene trimers and tetramers with different chromophores as blue-light-emitters
  作者：Xinyan Bai、Xueyi Chen、Jerry R. Dias、T.C. Sandreczki

  DOI：10.1016/j.tetlet.2013.01.076

  日期：2013.3

  A series of highly fluorescent p-phenylene-ethynylene pi-conjugated oligomers (trimers and tetramers) with different chromophore substituents have been synthesized stepwise under oxygen-free Sonogashira conditions. The emission wavelengths range from 400 to 455 nm for the series. All four trimers and tetramers have visible blue emission under sunlight especially for the case of the pyrene-substituted trimer and tetramer. All oligomers also exhibit very high quantum yields (0.9-1.1), which suggest that these types of compounds could be used as blue-light-emitters. (C) 2013 Elsevier Ltd. All rights reserved.