1,3,5-三苯基-3-(4-溴苯基)-1,5-戊二酮 | 119760-22-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3,5-三苯基-3-(4-溴苯基)-1,5-戊二酮
• 英文名称: 1,3,5-triphenyl-3-(4-bromophenyl)-1,5-pentanedione
• 英文别名: 3-p-bromophenyl-1,3,5-triphenylpentane-1,5-dione；3-(4-bromophenyl)-1,3,5-triphenylpentane-1,5-dione
• CAS: 119760-22-4
• 化学式: C₂₉H₂₃BrO₂
• 分子量: 483.404
• InChiKey: YYTHXRMLTUSUFM-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  632.3±55.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,3,5-三苯基-3-(4-溴苯基)-1,5-戊二酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以83%的产率得到4-(4-bromophenyl)-2,4,6-triphenyl-4H-pyran
  参考文献：
  名称：

  Schwarz, Marian; Trska, Petr; Kuthan, Josef, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 7, p. 1854 - 1869

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯甲酰苯 以37%的产率得到
  参考文献：
  名称：

  SHIBUYA, JUNKO;NABESHIMA, MAMI (NEE NAKAMURA);NAGANO, HAJIME;MAEDA, KOKO, J. CHEM. SOC. PERKIN TRANS. PT 2,(1988) N 8, C. 1607-1612

  摘要：

  DOI：

文献信息

• Photochemical reaction of 2,4,4,6-tetrasubstituted 1,4-dihydropyridines in deaerated media: photocolouration and photorearrangement accompanying dehydrogenation
  作者：Junko Shibuya、Mami Nabeshima (née Nakamura)、Hajime Nagano、Koko Maeda

  DOI：10.1039/p29880001607

  日期：——

  solutions and gave 1,3-diphenyl-2-azatriphenylene (8), 3-p-bromophenyl-2,4,6-triphenyl-pyridine (9), and 2,3,6-triphenyl-4-p-tolylpyridine (11), respectively. These reactions proceed through di-π-methane rearrangement accompanying dehydrogenation. 4-Benzyl-2,4,6-triphenyl-1,4-dihydro-pyridine (5) and 4-benzyl-1-methyl-2,4,6-triphenyl-1,4-dihydropyridine (6) showed very faint colouration on irradiation. Compound

  脱气溶液中2,2,4,6-四苯基-1,4-二氢吡啶（1）的光化学颜色变化已报告为光致变色现象，是无可逆转的变化，可产生无色至紫色。 2,3,4,6-四苯基吡啶（7）为主要产物。螺-[2,6-二苯基-1,4-二氢吡啶-4,9'-芴]（2），4-对-溴苯基-2,4,6-三苯基-1,4-二氢吡啶（3）和2,4,6-三苯基-4- p -甲苯基-1,4-二氢吡啶（4）也显示在脱气的溶液类似photocolour变化并给出1,3-二苯基-2-氮杂三亚苯（8），3- p -溴苯基-2,4,6-三苯基吡啶（9）和2,3,6-三苯基-4-对甲苯基吡啶（11）。这些反应通过伴随脱氢的二-π-甲烷重排进行。4-苄基-2,4,6-三苯基-1,4-二氢吡啶（5）和4-苄基-1-甲基-2,4,6-三苯基-1,4-二氢吡啶（6）显示非常微弱照射时着色。化合物（5）得到2,4,6-三苯基吡啶（12），其通过消除苄基和氢而
• Novel preparation and photochromic properties of 2,4,4,6-tetraaryl-4H-thiopyrans
  作者：Pavel Šbebek、Stanislav Nešpůrek、Richard Hrabal、Mojmír Adamec、Josef Kuthan

  DOI：10.1039/p29920001301

  日期：——

  compounds 3c, j, I, m, 4a–m, 6(the pyran analogue of 7) and 7 has been carried out. Compounds 4 and 7 undergo a reversible photochemical colour change after UV illumination. The maxima of the new absorption bands are situated at 540–660 nm. The non-exponential time dependence of the photodecolouration of 4a in the solid state is analysed in terms of dispersive first-order reaction kinetics. Dioxygen accelerates

  1,3,3,5-Tetraarylpentane -1,5-二酮2和5与tetraphosphodecasulfide反应在二甲苯中在升高的温度下，得到相应的2,4,4,6-四芳-4- ħ -thiopyrans 4和7。这种转化的机制涉及的脱水的快速初始步骤2和5至2,4,4,6-四芳-4- ħ -pyrans 3，随后较慢变换到4 ħ -噻喃类似物4。使用2D NMR技术，可以完全指定1-氧化物和1,1-二氧化物类似物的1 H和13 C NMR光谱已经进行了4（1，X = SO和SO 2）以及化合物3c，j，I，m，4a – m，6（吡喃类似物7）和7的合成。紫外线照射后，化合物4和7发生可逆的光化学颜色变化。新吸收带的最大值位于540–660 nm。4a光致脱色的非指数时间依赖性根据分散的一阶反应动力学分析了固态中的C -1。双氧加速了脱色过程；299 K的半衰期在空气中持续6600
• Photochemical reaction of 2,4,4,6-tetraaryl-4H-pyrans and -4H-thiopyrans with colour change by a 1,5-electrocyclic reaction. X-Ray molecular structure of 4-methyl-2,3,6-triphenyl-2H-thiopyran
  作者：Yukie Mori、Koko Maeda

  DOI：10.1039/p29910002061

  日期：——

  2,4,4,6-Tetraphenyl-4H-pyran and -4H-thiopyran exhibited a photochemical colour change in the solid state. On irradiation in solution, 2,4,4,6-tetraphenyl-4H-pyran gave 1,3,5,6-tetraphenyl-2-oxabicyclo[3.1.0]hex-3-ene, while the 4H-thiopyran gave 1,3,5,6-tetraphenyl-2-thiabicyclo[3.1.0]hex-3-ene as an initial photoproduct, followed by further transformation into 2,3,4,6-tetraphenyl-2H-thiopyran. 4-(4-Bromophenyl)-2,4,6-triphenyl-4H-pyran, 4-(4-methylphenyl)-2,4,6-triphenyl-4H-pyran, and 4-(4-bromophenyl)-2,4,6-triphenyl-4H-thiopyran also showed photochemical colour changes and finally gave both the phenyl-migrated and the (substituted phenyl)-migrated products in comparable yields in each case. 4-Methyl-2,4,6-triphenyl-4H-thiopyran showed no photochemical colour change in the solid state, but in solution it afforded 4-methyl-2,3,6-triphenyl-2H-thiopyran, whose structure was confirmed by X-ray analysis. Based on comparison with the photochemical behaviour of 2,4,4,6-tetraphenyl-1,4-dihydropyridine and 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazine, a six-membered ylide was proposed as the coloured photochemical intermediate.