1,4-Dibenzoyl-2,3-diphenyl-butan-2,3-diol | 10562-14-8

• 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
• 英文名称: 1,4-Dibenzoyl-2,3-diphenyl-butan-2,3-diol
• 英文别名: 3,4-dihydroxy-1,3,4,6-tetraphenylhexane-1,6-dione
• CAS: 10562-14-8
• 化学式: C₃₀H₂₆O₄
• 分子量: 450.534
• InChiKey: FQBWLFAVGVJPFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-羟基-1,3-二苯基丙烷-1-酮 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以15%的产率得到1,4-Dibenzoyl-2,3-diphenyl-butan-2,3-diol
  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

• First samarium-catalysed coupling of aldehydes and ketones
  作者：Elisabeth Léonard、Elisabet Duñach、Jacques Périchon

  DOI：10.1039/c39890000276

  日期：——

  The SmCl3 catalysed electrochemical coupling of carbonyl compounds affords 1,2-diols in good yields.

  SmCl 3催化的羰基化合物的电化学偶合以良好的产率提供1,2-二醇。
• LEONARD, ELISABETH;DUNACH, ELISABET;PERICHON, JACQUES, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 276-277
  作者：LEONARD, ELISABETH、DUNACH, ELISABET、PERICHON, JACQUES

  DOI：——

  日期：——