1,4-dibenzoyl-2,3-diphenyl-1,3-butadiene | 10562-16-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,4-dibenzoyl-2,3-diphenyl-1,3-butadiene
• 英文别名: 1,3,4,6-tetraphenyl-hexa-2,4-diene-1,6-dione；1,3,4,6-Tetraphenyl-hexa-2,4-dien-1,6-dion；α.ζ-Dioxo-α.γ.δ.ζ-tetraphenyl-β.δ-hexadien；β.γ-Diphenyl-α.δ-dibenzoyl-α.γ-butadien；1.4-Dibenzoyl-2.3-diphenyl-buta-1.3-dien；1,3,4,6-Tetraphenylhexa-2,4-diene-1,6-dione
• CAS: 10562-16-0
• 化学式: C₃₀H₂₂O₂
• 分子量: 414.503
• InChiKey: ROYPBZQYHFGGFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dibenzoyl-2,3-diphenyl-1,3-butadiene 在 溶剂黄146 、 锌 作用下， 生成 1,3,4,6-tetraphenylhexane-1,6-dione
  参考文献：
  名称：

  Wislicenus,J.; Lehmann, Justus Liebigs Annalen der Chemie, 1898, vol. 302, p. 202

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-Dibenzoyl-2,3-diphenyl-butan-2,3-diol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 1,4-dibenzoyl-2,3-diphenyl-1,3-butadiene
  参考文献：
  名称：

  Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines

  摘要：

  Photoinduced single electron transfer (SET) reactions of alpha,-beta-epoxy ketones have been studied using alkylamine electron donors. Irradiation of chalcone epoxide 1 with triethylamine (TEA) afforded beta-diketone 2 and beta-hydroxy ketone 3. Photoreaction of 1 with TEA in MeOH resulted in a slightly increased product ratio (3/2) compared with that in MeCN. When 1,4-diazabicyclo[2.2.2]octane (DABCO) was used instead of TEA, a decrease in the yield of 3 was observed. Only 2 was obtained on irradiation of a solution of 1 in TEA and MeCN containing LiClO4. Studies of photoreactions of dypnone epoxide 9, benzoylisopropylethylene epoxide 12, and acrylophenone epoxide 15 indicate that the nature of beta-substituent also influences the product distribution. It was also found that 1,6-bis(dimethylamino)pyrene (BDMAP) sensitizes the photoreaction of 1 in the presence of TEA to produce 2. Based on the results obtained, a reaction mechanism involving selective C-alpha-O bond cleavage of intermediate alpha,-beta-epoxy ketone anion radicals is proposed.

  DOI：

  10.1021/jo00004a052

文献信息

• Japp; Michie, Journal of the Chemical Society, 1901, vol. 79, p. 1015
  作者：Japp、Michie

  DOI：——

  日期：——
• Wislicenus; Lehmann, Justus Liebigs Annalen der Chemie, 1898, vol. 302, p. 195
  作者：Wislicenus、Lehmann

  DOI：——

  日期：——
• Notes - 1,4-Dibenzoyl-2,3-dipheyl-1,3-butadiene
  作者：Howard Bost、Philip Bailey

  DOI：10.1021/jo01113a607

  日期：1956.7
• LXXI.—Condensations of phenanthraquinone with ketonic compounds
  作者：Francis Robert Japp、James Wood

  DOI：10.1039/ct9058700712

  日期：——
• Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines
  作者：Eietsu Hasegawa、Kenyuki Ishiyama、Takaaki Horaguchi、Takahachi Shimizu

  DOI：10.1021/jo00004a052

  日期：1991.2

  Photoinduced single electron transfer (SET) reactions of alpha,-beta-epoxy ketones have been studied using alkylamine electron donors. Irradiation of chalcone epoxide 1 with triethylamine (TEA) afforded beta-diketone 2 and beta-hydroxy ketone 3. Photoreaction of 1 with TEA in MeOH resulted in a slightly increased product ratio (3/2) compared with that in MeCN. When 1,4-diazabicyclo[2.2.2]octane (DABCO) was used instead of TEA, a decrease in the yield of 3 was observed. Only 2 was obtained on irradiation of a solution of 1 in TEA and MeCN containing LiClO4. Studies of photoreactions of dypnone epoxide 9, benzoylisopropylethylene epoxide 12, and acrylophenone epoxide 15 indicate that the nature of beta-substituent also influences the product distribution. It was also found that 1,6-bis(dimethylamino)pyrene (BDMAP) sensitizes the photoreaction of 1 in the presence of TEA to produce 2. Based on the results obtained, a reaction mechanism involving selective C-alpha-O bond cleavage of intermediate alpha,-beta-epoxy ketone anion radicals is proposed.