(E)-1-[4-(dimethylamino)phenyl]pent-1-en-4-yn-3-ol | 164118-85-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1-[4-(dimethylamino)phenyl]pent-1-en-4-yn-3-ol
• 英文别名: trans-HC*C-CHOH-CH=CH-p-PhNMe2；1-(4-(dimethylamino)phenyl)pent-1-en-4-yn-3-ol
• CAS: 164118-85-8
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: MRTOJXHRNAPVKR-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-溴吡啶 、 (E)-1-[4-(dimethylamino)phenyl]pent-1-en-4-yn-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 以54%的产率得到(1E,4E)-1-[4-(dimethylamino)phenyl]-5-(pyridin-4-yl)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
• 作为产物：
  描述：

  3-(4-dimethylamino-phenyl)-propenal 、 乙炔基溴化镁 以 四氢呋喃 为溶剂， 反应 2.17h， 以79%的产率得到(E)-1-[4-(dimethylamino)phenyl]pent-1-en-4-yn-3-ol
  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。
• Domino synthesis of protochromic “ON–OFF–ON” luminescent 2-styryl quinolines
  作者：Rahime Cinar、Jan Nordmann、Elena Dirksen、Thomas J. J. Müller

  DOI：10.1039/c3ob27270b

  日期：——

  The microwave-assisted coupling-isomerization reaction (MACIR) opens a straightforward domino access to 2-styryl quinolines in good to excellent yields. The push–pull character of these lumophores can be enhanced by placing a dimethyl amino group as an auxochrome in the para-position of the styryl moiety whereas anti-auxochromes are located in the 6-position of the quinoline part. The optical absorption and emission properties of the compounds were studied in solvents of different polarity and at various pH. The pronounced proto- and solvochromicity of the absorption and emission properties qualify them as luminescent pH sensors with “ON–OFF–ON” emission profiles triggered by pH variation over a broad pH range. The electronic structure of the chromophores is rationalized by DFT calculations.

  微波辅助偶联-异构化反应（MACIR）开辟了一种直接获得 2-苯乙烯基喹啉类化合物的多米诺途径，产量从良好到极佳。通过将二甲基氨基作为辅助色素置于苯乙烯基分子的对位，而将反辅助色素置于喹啉部分的 6 位，可以增强这些发光体的推拉特性。研究人员在不同极性和不同 pH 值的溶剂中对这些化合物的光学吸收和发射特性进行了研究。这些化合物的吸收和发射特性具有明显的原色和溶色性，因此可用作 pH 值发光传感器，其 "ONâOFFâONâ "发射曲线可在广泛的 pH 值范围内由 pH 值变化触发。发色团的电子结构通过 DFT 计算得到了合理解释。
• Novel Ruthenium Allenylidene and Mixed Alkynyl Allenylidene Complexes:  Crystal Structure of <i>trans</i>-[(Ph₂PCH₂CH₂PPh₂)₂Ru(C⋮CPh)(CCCPh₂)]PF₆
  作者：Daniel Touchard、Pierre Haquette、Alain Daridor、Antonio Romero、Pierre H. Dixneuf

  DOI：10.1021/om980273r

  日期：1998.8.1

  cis-RuCl2(dppe)(2) (1) (dppe = Ph2PCH2CH2PPh2) reacts with propargylic alcohols, HC=(CCRROH)-R-1-O-2, and NaPF6 to give a variety of allenylidene complexes trans-[(dppe)(2)(Cl)Ru+=C=C=(CRR2)-R-1]PF6 (6). The subtitution of the chloride from vinylidene trans-[(dppe)(2)(Cl)Ru=C=CHR] cations, in the presence of a base, by a variety of propargylic alcohols constitutes the easiest way to selectively produce complexes containing both the alkynyl and the allenylidene groups, trans-[(dppe)(2)Ru(C=CR)(=C=C=(CRR2)-R-1)]PF6 (7, 8). These derivatives have been fully characterized by IR, H-1, C-13, and P-31 NMR. Single-crystal X-ray diffraction is determined for 7c (R = R-1 = R-2 = Ph). Complexes 7 react with strong nucleophiles such as NaOMe or NaBH4 to form exclusively unsymmetrical bis(acetylide) complexes by addition of H- or MeO- on the carbon C(3) of the allenylidene ligand. Cyclic voltammetry of complexes 6 and 7 shows the marked influence of the terminal groups of the allenylidene ligands on the reduction of the ruthenium(II) center.
• 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.