1-ethynylacenaphthylene | 135509-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 吖萘类
• 英文名称: 1-ethynylacenaphthylene
• 英文别名: Acenaphthylene, 1-ethynyl-
• CAS: 135509-94-3
• 化学式: C₁₄H₈
• 分子量: 176.218
• InChiKey: QTWZUODXLMGIRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 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

• 作为产物：
  描述：

  1-bromoacenaphthylene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 1-ethynylacenaphthylene
  参考文献：
  名称：

  Sarobe, Martin; Flink, Simon; Jenneskens, Leonardus W., Journal of the Chemical Society. Perkin transactions II, 1996, # 10, p. 2125 - 2132

  摘要：

  DOI：

文献信息

• The ethyne-ethylidene rearrangement: Formation of 3-ethynyl-and 1-ethynylacenaphthylene on flash vacuum pyrolysis of 1,7-diethynylnaphthalene
  作者：Roger F.C. Brown、Frank W. Eastwood、Neil R. Wong

  DOI：10.1016/s0040-4039(00)77534-4

  日期：1993.2

  1,7-Diethynylnaphthalene on flash vacuum pyrolysis at 1100°C/0.05 mm gave 3-ethynylacenaphthylene and 1-ethynylacenaphthylene (80:20). This finding is interpreted in terms of initial formation of 3-ethynylacepnaphthylene, ring closure of some of this compound to the hypothetical cyclopent[bc]acenaphthylene and cleavage to give 1-ethynyl- and 3-ethynylacenaphthylene.

  在1100℃/ 0.05mm下的快速真空热解中的1，7-二乙炔基萘得到3-乙炔基间萘和1-乙炔基间萘（80∶20）。这一发现是根据3-乙炔基乙炔的初始形成，该化合物中某些化合物与假定的环戊[ bc ] ena烯的开环闭合和裂解得到1-乙炔基-和3-乙炔基ena烯而解释的。
• Adeney, Michael; Brown, Roger F. C.; Coulston, Karen J., Australian Journal of Chemistry, 1991, vol. 44, # 7, p. 967 - 980
  作者：Adeney, Michael、Brown, Roger F. C.、Coulston, Karen J.、Eastwood, Frank W.、James, Ian W.

  DOI：——

  日期：——
• 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.