2-(1-chloroethenyl)phenanthrene | 228266-64-6

• 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: 2-(1-chloroethenyl)phenanthrene
• CAS: 228266-64-6
• 化学式: C₁₆H₁₁Cl
• 分子量: 238.716
• InChiKey: RTZOGIHRQLCCGP-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  418.6±14.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 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-(1-chloroethenyl)phenanthrene 900.0 ℃ 、1.33 Pa 条件下， 以98%的产率得到2-乙炔基菲
  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：

  2-乙酰基菲 在 五氯化磷 、 三氯化磷 作用下， 反应 24.0h， 以57%的产率得到2-(1-chloroethenyl)phenanthrene
  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

文献信息

• 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.