2-氯-2-氟-1,3-双(4-甲氧基苯基)丙烷-1,3-二酮 | 952724-65-1

• 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: 2-氯-2-氟-1,3-双(4-甲氧基苯基)丙烷-1,3-二酮
• 英文名称: 2-chloro-2-fluoro-1,3-bis(4-methoxyphenyl)propane-1,3-dione
• 英文别名: 2-chloro-2-fluoro-1,3-di(4-methoxyphenyl)propan-1,3-dione
• CAS: 952724-65-1
• 化学式: C₁₇H₁₄ClFO₄
• 分子量: 336.747
• InChiKey: DIROVFPLXAWDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯-2-氟-1,3-双(4-甲氧基苯基)丙烷-1,3-二酮 以 乙腈 为溶剂， 反应 2.0h， 生成 4',6-dimethoxy-3-fluoroflavone 、 4-甲氧基苯甲醛 、 大茴香酸
  参考文献：
  名称：

  Photocyclization of 2-Chloro-Substituted 1,3-Diarylpropan-1,3-diones to Flavones

  摘要：

  The photochemical behavior of 2-halo-substituted 1,3-diarylpropan-1,3-dione strongly depends on the nature of the halogen atom bonded and the presence of electron-donor groups on the phenyl ring. In the case of 2-chloro-1,3-diphenylpropan-1,3-dione and 1-(3,5-dimethoxyphenyl)-3-phenylpropan-1,3-dione, cyclization to flavones was the sole reaction pathway, whereas in the case of 2-chloro-1,3-di(4-methoxyphenyl)propan-1,3-dione, only products derived from alpha-cleavage were observed. 2-Fluoro derivatives of 1,3-diarylpropan-1,3-diones were photostable; on the other hand, 2-chloro-2-fluoro derivates resulted in 3-fluoroflavones.

  DOI：

  10.1021/ol701654c
• 作为产物：
  描述：

  1,3-双(4-甲氧基苯基)1,3-丙二酮 在 N-氯代丁二酰亚胺 、 lithium perchlorate 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 21.5h， 生成 2-氯-2-氟-1,3-双(4-甲氧基苯基)丙烷-1,3-二酮
  参考文献：
  名称：

  Photocyclization of 2-Chloro-Substituted 1,3-Diarylpropan-1,3-diones to Flavones

  摘要：

  The photochemical behavior of 2-halo-substituted 1,3-diarylpropan-1,3-dione strongly depends on the nature of the halogen atom bonded and the presence of electron-donor groups on the phenyl ring. In the case of 2-chloro-1,3-diphenylpropan-1,3-dione and 1-(3,5-dimethoxyphenyl)-3-phenylpropan-1,3-dione, cyclization to flavones was the sole reaction pathway, whereas in the case of 2-chloro-1,3-di(4-methoxyphenyl)propan-1,3-dione, only products derived from alpha-cleavage were observed. 2-Fluoro derivatives of 1,3-diarylpropan-1,3-diones were photostable; on the other hand, 2-chloro-2-fluoro derivates resulted in 3-fluoroflavones.

  DOI：

  10.1021/ol701654c

文献信息

• Investigations on the Photochemical Reaction Mechanisms of Selected Dibenzoylmethane Compounds
  作者：Junxiao Wang、Yan Guo、Jialin Wang、Jiani Ma

  DOI：10.1021/acs.joc.1c00647

  日期：2021.6.4

  In this work, combined time-resolved spectroscopies of femtosecond transient absorption, nanosecond transient absorption, and DFT calculations were performed to unravel the photocyclization reaction mechanisms of selected dibenzoylmethane (DBM) derivatives, including 2-chloro-1,3-diphenylpropan-1,3-dione (1a), 2-chloro-1-(3,5-dimethoxyphenyl)-3-phenylpropan-1,3-dione (1b), 2-chloro-2-fluoro-1,3-diphenylpropan-1

  在这项工作中，进行了飞秒瞬态吸收、纳秒瞬态吸收和 DFT 计算的组合时间分辨光谱，以揭示选定的二苯甲酰甲烷 (DBM) 衍生物的光环化反应机制，包括 2-chloro-1,3-diphenylpropan-1， 3-二酮 ( 1a ), 2-氯-1-(3,5-二甲氧基苯基)-3-苯基丙-1,3-二酮 ( 1b ), 2-氯-2-氟-1,3-二苯基丙-1, 3-二酮( 1c )和2-氯-2-氟-1,3-二(4-甲氧基苯基)丙-1,3-二酮( 1d )。1a和1b的光环化反应机理是相似的，其中发生 C-Cl 杂解产生 α-酮阳离子中间体，然后环化以产生阳离子物质。另一方面，1c和1d进行脱氯主要产生自由基物种，其进一步经历环化产生环化自由基物种。导致不同反应机制的主要因素是在 α-C 键合的氟原子的参与。由于meta效应，苯环上的对甲氧基取代抑制了光环化反应，降低了光环化的产率。
• Photocyclization of 2-Chloro-Substituted 1,3-Diarylpropan-1,3-diones to Flavones
  作者：Berta Košmrlj、Boris Šket

  DOI：10.1021/ol701654c

  日期：2007.9.1

  The photochemical behavior of 2-halo-substituted 1,3-diarylpropan-1,3-dione strongly depends on the nature of the halogen atom bonded and the presence of electron-donor groups on the phenyl ring. In the case of 2-chloro-1,3-diphenylpropan-1,3-dione and 1-(3,5-dimethoxyphenyl)-3-phenylpropan-1,3-dione, cyclization to flavones was the sole reaction pathway, whereas in the case of 2-chloro-1,3-di(4-methoxyphenyl)propan-1,3-dione, only products derived from alpha-cleavage were observed. 2-Fluoro derivatives of 1,3-diarylpropan-1,3-diones were photostable; on the other hand, 2-chloro-2-fluoro derivates resulted in 3-fluoroflavones.