(1E,4E)-1-(4-(dimethylamino)phenyl)-5-(4-(trifluoromethyl)phenyl)penta-1,4-dien-3-one | 1275577-02-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1-(4-(dimethylamino)phenyl)-5-(4-(trifluoromethyl)phenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-[4-(dimethylamino)phenyl]-5-[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-one；(1E,4E)-1-[4-(Dimethylamino)phenyl]-5-[4-(trifluoromethyl)phenyl]-1,4-pentadiene-3-one
• CAS: 1275577-02-0
• 化学式: C₂₀H₁₈F₃NO
• 分子量: 345.364
• InChiKey: BLHUYOHPYSJALD-FNCQTZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-dimethylamino-phenyl)-propenal 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.92h， 生成 (1E,4E)-1-(4-(dimethylamino)phenyl)-5-(4-(trifluoromethyl)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling–Isomerization Reaction

  摘要：

  As a twofold Michael system, the diarylideneacetone core is of particular interest in organic synthesis and for therapeutic applications. To overcome the drawbacks of the classical Claisen-Schmidt protocol, a new methodology for the synthesis of dissymmetric (hetero)diarylideneacetones has been developed. Conditions were optimized with a Box-Behnken design of experiment. The milder reaction conditions allow the efficient preparation of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be obtained through the classical Claisen-Schmidt protocol.

  DOI：

  10.1055/s-0032-1316811

文献信息

• COMPOUNDS USEFUL AGAINST KINETOPLASTIDEAE PARASITES
  申请人：Davioud-Charvet Elisabeth

  公开号：US20120214996A1

  公开（公告）日：2012-08-23

  Dibenzylidene and heterobenzylideneacetone derivatives, related 4-piperidones, related 4-thiopyranones and the corresponding sulfinyl- and sulfonyl-analogues for their use for prophylaxis or treatment of trypanosomiasis and leishmaniasis.

  二苄基亚烷和杂二苄基亚烷乙酮衍生物，相关的4-哌啶酮，相关的4-噻opyranones以及相应的亚磺酰基和磺酰基类似物，用于预防或治疗锥虫病和利什曼病。
• Compounds useful against kinetoplastideae parasites
  申请人：Davioud-Charvet Elisabeth

  公开号：US09174960B2

  公开（公告）日：2015-11-03

  Dibenzylidene and heterobenzylideneacetone derivatives, related 4-piperidones, related 4-thiopyranones and the corresponding sulfinyl- and sulfonyl-analogues for their use for prophylaxis or treatment of trypanosomiasis and leishmaniasis.

  二苯基乙烯和杂苯基乙烯酮衍生物、相关的4-哌啶酮、相关的4-硫代吡喃酮及其对应的亚磺酰基-和磺酰基-类似物，用于预防或治疗锥虫病和利什曼病。
• Synthesis and Structure−Affinity Relationships of Novel Dibenzylideneacetone Derivatives as Probes for β-Amyloid Plaques
  作者：Mengchao Cui、Masahiro Ono、Hiroyuki Kimura、Boli Liu、Hideo Saji

  DOI：10.1021/jm101404k

  日期：2011.4.14

  A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A beta(1-42) aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two F-18 fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity folr A beta(1-42) aggregates (K-i ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for beta-amyloid imaging probes.
• US9174960B2
  申请人：——

  公开号：US9174960B2

  公开（公告）日：2015-11-03
• Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling–Isomerization Reaction
  作者：Thomas Müller、Thibault Gendron、Elisabeth Davioud-Charvet

  DOI：10.1055/s-0032-1316811

  日期：——

  As a twofold Michael system, the diarylideneacetone core is of particular interest in organic synthesis and for therapeutic applications. To overcome the drawbacks of the classical Claisen-Schmidt protocol, a new methodology for the synthesis of dissymmetric (hetero)diarylideneacetones has been developed. Conditions were optimized with a Box-Behnken design of experiment. The milder reaction conditions allow the efficient preparation of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be obtained through the classical Claisen-Schmidt protocol.