bis[p-diethynylbenzene] | 124417-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis[p-diethynylbenzene]
• 英文别名: 1,4-bis(4-ethynylphenyl)buta-1,3-diyne；1-Ethynyl-4-[4-(4-ethynylphenyl)buta-1,3-diynyl]benzene
• CAS: 124417-94-3
• 化学式: C₂₀H₁₀
• 分子量: 250.299
• InChiKey: HNWVMLRROYFBLF-UHFFFAOYSA-N

物化性质

• 熔点：
  148-151 °C
• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• 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：

  dicobalt octacarbonyl 、 bis[p-diethynylbenzene] 以 not given 为溶剂， 以21%的产率得到[(Co2(CO)6)4(μ8-η(2:2:2:2:2:2:2:2)-HC2C6H4C2C2C6H4C2H)]
  参考文献：
  名称：

  Novel acetylene-linked di-cobalt and tetra-cobalt carbonyl clusters

  摘要：

  {Co-2(CO)(6)} groups were attached to p-diethynylbenzene-based acetylenes giving complexes of general formula [{Co-2(CO)(6){(mu(2)-eta(2:2)-RC2C6H4C2R')] ((4): R = R' = H; (4a): R = SiMe3, R' = H; (4b): R = R' = SiMe3); [{Co-2(CO)(6)}(2)(mu(4)-eta(2:2:2:2)-RC2C6H4C2R')] ((3): R = R' = H; (3a): R = SiMe3, R' = H; (3b): R = R' = SiMe3); [{Co-2(CO)(6)}(4)(mu(8)-eta(2:2:2:2:2:2:2:2)-R2C6H4C2C2C6H4C2R)]((5): R = H; (5b):R = SiMe3). The addition of Co-4(CO)(12) to p-diethynylbenzene and to 4 was also investigated, producing [{Co-4(CO)(8)(mu-CO)(2)}(mu(4)-HC2C6H4C2H)] (6) and [{Co-2(CO)(6)} {(Co-4(CO)(8)(mu-CO)(2)}(mu(8)-HC2C6H4C2H)] (7). The syntheses of the acetylenic derivatives of C-60 [(trimethylsilyl)ethynyl] hydrofullerene [60] (8a) and (phenylethynyl) hydrofullerene[60] (9) and the new ligand [(trimethylsilyl)diethynylbenzene]hydrofullerene[60] (10a) were performed and the resulting acetylenes were reacted with dicobaltoctacarbonyl giving the corresponding complexes [(trimethylsilyl)(dicobalthexacarbonyl)ethynyl]hydrofullerene[60] (11a), (phenylethynyl)(dicobalthexacarbonyl)hydrofullerene[60] (12) and [(trimethylsilyl)bis(dicobalthexacarbonyl)diethynylbenzene] (13a). The reaction of 1-bromo-3,5-diethynylbenzene and 1,3,5-triethynylbenzene with dicobaltoctacarbonyl resulted in the formation of [HC2{Co-2(CO)(6)}](2)C6H2Br (16) and [HC2{Co-2(CO)(6)}](2)C6H3 (15) as expected. Crystals of 3a, 3b, 4, 4b, 15 and 16 suitable for single-crystal X-ray diffraction were grown and the molecular structures of these compounds an discussed. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00399-x
• 作为产物：
  描述：

  1,4-bis-1,3-butadiyne 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以90%的产率得到bis[p-diethynylbenzene]
  参考文献：
  名称：

  Novel acetylene-linked di-cobalt and tetra-cobalt carbonyl clusters

  摘要：

  {Co-2(CO)(6)} groups were attached to p-diethynylbenzene-based acetylenes giving complexes of general formula [{Co-2(CO)(6){(mu(2)-eta(2:2)-RC2C6H4C2R')] ((4): R = R' = H; (4a): R = SiMe3, R' = H; (4b): R = R' = SiMe3); [{Co-2(CO)(6)}(2)(mu(4)-eta(2:2:2:2)-RC2C6H4C2R')] ((3): R = R' = H; (3a): R = SiMe3, R' = H; (3b): R = R' = SiMe3); [{Co-2(CO)(6)}(4)(mu(8)-eta(2:2:2:2:2:2:2:2)-R2C6H4C2C2C6H4C2R)]((5): R = H; (5b):R = SiMe3). The addition of Co-4(CO)(12) to p-diethynylbenzene and to 4 was also investigated, producing [{Co-4(CO)(8)(mu-CO)(2)}(mu(4)-HC2C6H4C2H)] (6) and [{Co-2(CO)(6)} {(Co-4(CO)(8)(mu-CO)(2)}(mu(8)-HC2C6H4C2H)] (7). The syntheses of the acetylenic derivatives of C-60 [(trimethylsilyl)ethynyl] hydrofullerene [60] (8a) and (phenylethynyl) hydrofullerene[60] (9) and the new ligand [(trimethylsilyl)diethynylbenzene]hydrofullerene[60] (10a) were performed and the resulting acetylenes were reacted with dicobaltoctacarbonyl giving the corresponding complexes [(trimethylsilyl)(dicobalthexacarbonyl)ethynyl]hydrofullerene[60] (11a), (phenylethynyl)(dicobalthexacarbonyl)hydrofullerene[60] (12) and [(trimethylsilyl)bis(dicobalthexacarbonyl)diethynylbenzene] (13a). The reaction of 1-bromo-3,5-diethynylbenzene and 1,3,5-triethynylbenzene with dicobaltoctacarbonyl resulted in the formation of [HC2{Co-2(CO)(6)}](2)C6H2Br (16) and [HC2{Co-2(CO)(6)}](2)C6H3 (15) as expected. Crystals of 3a, 3b, 4, 4b, 15 and 16 suitable for single-crystal X-ray diffraction were grown and the molecular structures of these compounds an discussed. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00399-x

文献信息

• Palladium-catalyzed acylation and/or homo-coupling of aryl- and alkyl-acetylenes
  作者：Serena Perrone、Fabio Bona、Luigino Troisi

  DOI：10.1016/j.tet.2011.07.032

  日期：2011.9

  Allyl or benzyl halides, through a Pd(0)-catalyzed reaction and under CO pressure, generate acyl-palladium/halides that, in the presence of a base and an aryl- and alkyl-acetylene, undergo nucleophilic acyl substitution giving conjugated acetylenic ketones. Diynes, resulting from allcyne/alkyne homo-coupling, were instead the main products in reactions performed without allyl or benzyl halides. Moreover, dimerization, trimerization, and cyclotrimerization reactions of acetylenes were observed in reaction carried out even without base. (C) 2011 Elsevier Ltd. All rights reserved.