1-(4-叔丁基苯基)-2-癸基-3-(4-甲氧基苯基)丙烷-1,3-二酮 | 828911-21-3

• 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-(4-叔丁基苯基)-2-癸基-3-(4-甲氧基苯基)丙烷-1,3-二酮
• 英文名称: 1-(4-tert-butylphenyl)-2-decanyl-3-(4-methoxyphenyl)propane-1,3-dione
• 英文别名: C10-DBM；3-(4-tert-butylphenyl)-2-decanyl-1-(4-methoxyphenyl)propane-1,3-dione；1-(4-t-Butylphenyl)-2-decanyl-3-(4'-methoxyphenyl)-propane 1,3-dione；1-(4-tert-butylphenyl)-2-decyl-3-(4-methoxyphenyl)propane-1,3-dione
• CAS: 828911-21-3
• 化学式: C₃₀H₄₂O₃
• 分子量: 450.662
• InChiKey: OYGPDIGLEKMQFB-UHFFFAOYSA-N

物化性质

• 沸点：
  572.4±40.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-叔丁基苯基)-2-癸基-3-(4-甲氧基苯基)丙烷-1,3-二酮 以 正己烷 为溶剂， 反应 3.0h， 生成 正癸烯 、 (Z)-1-(4-tert-butylphenyl)-3-hydroxy-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Photochemical Behavior of a New Long-chain UV Absorber† Derived from 4-tert-Butyl-4′-Methoxydibenzoylmethane¶

  摘要：

  A new UV filter, the 1-(4-tert-butylphenyl)-2-decanyl-3-(4'-methoxyphenyl)-propane-1,3-dione, called C10-DBM, was prepared by grafting a 10-carbon aliphatic chain to the alpha-carbonyl position of 4-tert-butyl-4'-methoxydibenzoylmethane (BM-DBM), a well-known and often used UV filter. The UV-A absorption efficiency of organic solutions containing the new filter was tested and compared with identical solutions containing BM-DBM with or without irradiation (xenon lamp). The originality of this new filter is that its UV-A absorbance appeared during irradiation of the molecule. Although the molar absorption coefficient of C10-DBM in the UV-A domain was lower than that of BM-DBM, the solutions absorption exhibited a much more photostable behavior under irradiation. In this study, we first demonstrated that C10-DBM was a precursor of BM-DBM (enol isomer) by means of high-performance liquid chromatography followed by mass spectrometry. Indeed, we showed that the UV-A absorption of C10-DBM solutions appearing during the irradiation of the molecule was due to a Norrish-II reaction (beta-cleavage), which induced the release of the BM-DBM enol form and 1-decene. Then, we established a kinetic model for the photochemistry of C10-DBM and fitted the variation of UV absorption spectra to confirm the proposed mechanism.

  DOI：

  10.1562/2004-03-09-ra-106.1
• 作为产物：
  描述：

  癸基溴 、 阿伏苯宗 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以42%的产率得到1-(4-叔丁基苯基)-2-癸基-3-(4-甲氧基苯基)丙烷-1,3-二酮
  参考文献：
  名称：

  Photochemical Behavior of a New Long-chain UV Absorber† Derived from 4-tert-Butyl-4′-Methoxydibenzoylmethane¶

  摘要：

  A new UV filter, the 1-(4-tert-butylphenyl)-2-decanyl-3-(4'-methoxyphenyl)-propane-1,3-dione, called C10-DBM, was prepared by grafting a 10-carbon aliphatic chain to the alpha-carbonyl position of 4-tert-butyl-4'-methoxydibenzoylmethane (BM-DBM), a well-known and often used UV filter. The UV-A absorption efficiency of organic solutions containing the new filter was tested and compared with identical solutions containing BM-DBM with or without irradiation (xenon lamp). The originality of this new filter is that its UV-A absorbance appeared during irradiation of the molecule. Although the molar absorption coefficient of C10-DBM in the UV-A domain was lower than that of BM-DBM, the solutions absorption exhibited a much more photostable behavior under irradiation. In this study, we first demonstrated that C10-DBM was a precursor of BM-DBM (enol isomer) by means of high-performance liquid chromatography followed by mass spectrometry. Indeed, we showed that the UV-A absorption of C10-DBM solutions appearing during the irradiation of the molecule was due to a Norrish-II reaction (beta-cleavage), which induced the release of the BM-DBM enol form and 1-decene. Then, we established a kinetic model for the photochemistry of C10-DBM and fitted the variation of UV absorption spectra to confirm the proposed mechanism.

  DOI：

  10.1562/2004-03-09-ra-106.1

文献信息

• Dibenzoilmethane derivative compounds, the use thereof in the form of photoactivable solar filters and cosmetic compositions containing said compounds
  申请人：Rico-Lattes Isabelle

  公开号：US20070025930A1

  公开（公告）日：2007-02-01

  The present invention relates to dibenzoylmethane-based compounds of formula 1, and also to salts or solvates thereof, and to the process for preparing them. The invention also relates to the use of a compound of formula (I) as an agent for protecting the skin or the hair against UV radiation and to a cosmetic and/or dermatological product, characterized in that it comprises a compound of formula (I) as active principle.

  本发明涉及公式1的二苯甲酮基化合物，以及其盐或溶剂化物，以及其制备过程。本发明还涉及将公式（I）化合物用作保护皮肤或头发免受紫外线辐射的剂量，以及化妆品和/或皮肤科产品，其特征在于其包含公式（I）化合物作为活性成分。
• US7446230B2
  申请人：——

  公开号：US7446230B2

  公开（公告）日：2008-11-04
• Photochemical Behavior of a New Long-chain UV Absorber† Derived from 4-tert-Butyl-4′-Methoxydibenzoylmethane¶
  作者：Fabienne Wetz、Corinne Routaboul、Dominique Lavabre、Jean-Christophe Garrigues、Isabelle Rico-Lattes、Ingrid Pernet、Alain Denis

  DOI：10.1562/2004-03-09-ra-106.1

  日期：——

  A new UV filter, the 1-(4-tert-butylphenyl)-2-decanyl-3-(4'-methoxyphenyl)-propane-1,3-dione, called C10-DBM, was prepared by grafting a 10-carbon aliphatic chain to the alpha-carbonyl position of 4-tert-butyl-4'-methoxydibenzoylmethane (BM-DBM), a well-known and often used UV filter. The UV-A absorption efficiency of organic solutions containing the new filter was tested and compared with identical solutions containing BM-DBM with or without irradiation (xenon lamp). The originality of this new filter is that its UV-A absorbance appeared during irradiation of the molecule. Although the molar absorption coefficient of C10-DBM in the UV-A domain was lower than that of BM-DBM, the solutions absorption exhibited a much more photostable behavior under irradiation. In this study, we first demonstrated that C10-DBM was a precursor of BM-DBM (enol isomer) by means of high-performance liquid chromatography followed by mass spectrometry. Indeed, we showed that the UV-A absorption of C10-DBM solutions appearing during the irradiation of the molecule was due to a Norrish-II reaction (beta-cleavage), which induced the release of the BM-DBM enol form and 1-decene. Then, we established a kinetic model for the photochemistry of C10-DBM and fitted the variation of UV absorption spectra to confirm the proposed mechanism.