4-乙炔基菲 | 69320-05-4

• 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: 4-乙炔基菲
• 英文名称: 4-ethynylphenanthrene
• 英文别名: 4-Ethynylphenanthrene
• CAS: 69320-05-4
• 化学式: C₁₆H₁₀
• 分子量: 202.255
• InChiKey: UQISARXAVAUPBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：

  4-乙炔基菲 800.0 ℃ 、1.33 Pa 条件下， 以100%的产率得到芘
  参考文献：
  名称：

  Origin of Pyrene under High Temperature Conditions in the Gas Phase. The Pivotal Role of Phenanthrene

  摘要：

  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.

  DOI：

  10.1021/jo982030e
• 作为产物：
  描述：

  4-羟基菲 在 bis(triphenylphosphine)palladium(II)-chloride copper(l) iodide 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 三乙胺 为溶剂， 反应 20.0h， 生成 4-乙炔基菲
  参考文献：
  名称：

  从扶手椅到纳米石墨烯的锯齿形外围

  摘要：

  基于合适的低聚亚苯基前体的分子内环化脱氢反应，提出了合成大的、非完全苯类多环芳烃 (PAH) 的合成概念，该多环芳烃装饰有相形成和增溶正十二烷基链。将连续的 C2 单元正式添加到母体六邻六苯并晕苯的扶手椅隔间中，扩展了芳香系统并导致具有部分锯齿形外围的多环芳烃。这种外围性质、对称性、大小和形状的变化对电子特性和柱状上层结构的组织有明显的影响。计算和实验 UV/vis 光谱都非常一致，强调特征带 alpha、p 和 beta 对 PAH 的整体大小和对称性的依赖性。虽然连接的正十二烷基链的数量和取代模式不影响电子性质，但热行为和超分子组织受到强烈影响，这已通过差示扫描量热法 (DSC) 和 2D 广角 X 射线衍射法阐明(2D-WAXS) 在机械对齐的样品上。这项研究为基于扩展多环芳烃的半导体材料的未来设计提供了宝贵的见解。

  DOI：

  10.1021/ja062026h

文献信息

• Visible-Light-Mediated Deacylated Alkynylation of Unstrained Ketone
  作者：Hao Wu、Shuguang Chen、Dengmengfei Xiao、Feng Li、Kaiyuan Zhou、Xiaocui Yin、Chunni Liu、Xinwei He、Yongjia Shang

  DOI：10.1021/acs.orglett.3c00145

  日期：2023.2.24

  Deconstructive alkynylation of an unstrained ketone catalyzed by an organic photocatalyst under blue light irradiation is reported for the first time. A broad substrate scope with up to 63 examples, excellent functional group tolerance, and gram scale reaction demonstrated the practicality of this novel alkynylation method. The dihydroquinazolinone derivative of trifluoroacetophenone had been proved

  首次报道了在蓝光照射下由有机光催化剂催化的未应变酮的解构炔基化。具有多达 63 个实例的广泛底物范围、出色的官能团耐受性和克级反应证明了这种新型炔基化方法的实用性。三氟苯乙酮的二氢喹唑啉酮衍生物在与各种炔基溴化物的三氟甲基化反应中表现良好，已被证明具有作为新型三氟甲基化试剂的潜力。
• Studies of magnetic anisotropy. 2. NMR evidence for the existence of deshielding regions alongside carbon-carbon triple bonds
  作者：Frank B. Mallory、Mary B. Baker

  DOI：10.1021/jo00182a001

  日期：1984.4
• From Armchair to Zigzag Peripheries in Nanographenes
  作者：Marcel Kastler、Jochen Schmidt、Wojciech Pisula、Daniel Sebastiani、Klaus Müllen

  DOI：10.1021/ja062026h

  日期：2006.7.1

  hydrocarbons (PAHs), decorated with phase-forming and solubilizing n-dodecyl chains, are presented based on the intramolecular cyclodehydrogenation reaction of suitable oligophenylene precursors. The formal addition of successive C2 units into the armchair bays of the parent hexa-peri-hexabenzocoronene extends the aromatic system and leads to PAHs with a partial zigzag periphery. This variation of the

  基于合适的低聚亚苯基前体的分子内环化脱氢反应，提出了合成大的、非完全苯类多环芳烃 (PAH) 的合成概念，该多环芳烃装饰有相形成和增溶正十二烷基链。将连续的 C2 单元正式添加到母体六邻六苯并晕苯的扶手椅隔间中，扩展了芳香系统并导致具有部分锯齿形外围的多环芳烃。这种外围性质、对称性、大小和形状的变化对电子特性和柱状上层结构的组织有明显的影响。计算和实验 UV/vis 光谱都非常一致，强调特征带 alpha、p 和 beta 对 PAH 的整体大小和对称性的依赖性。虽然连接的正十二烷基链的数量和取代模式不影响电子性质，但热行为和超分子组织受到强烈影响，这已通过差示扫描量热法 (DSC) 和 2D 广角 X 射线衍射法阐明(2D-WAXS) 在机械对齐的样品上。这项研究为基于扩展多环芳烃的半导体材料的未来设计提供了宝贵的见解。
• 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.