1-(4-dimethylaminophenyl)-3-(2-hydroxyphenyl)-2-propen-1-one | 59817-20-8

• 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-dimethylaminophenyl)-3-(2-hydroxyphenyl)-2-propen-1-one
• 英文别名: trans-4'-dimethylamino-2-hydroxychalcone；2-hydroxy-4'-(dimethylamino)chalcone；(E)-1-(4'-(dimethylamino)phenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one；(E)-1-[4-(dimethylamino)phenyl]-3-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 59817-20-8
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: CUYFIWYNYBJTGK-FMIVXFBMSA-N

物化性质

• 沸点：
  464.1±45.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-dimethylaminophenyl)-3-(2-hydroxyphenyl)-2-propen-1-one 在 高氯酸 作用下， 以 乙二醇二甲醚 为溶剂， 生成 2-(4-dimethylamino-phenyl)-chromenylium; perchlorate
  参考文献：
  名称：

  3-(2-Hydroxyphenyl)-1-(取代苯基)-2-propen-1-ones（取代的 2-Hydroxychalcones）在有机溶剂中在酸存在和不存在的情况下的光反应

  摘要：

  在有机溶剂中，在添加和不添加酸的情况下，研究了十几种 3-(2-羟基苯基)-1-(取代苯基)-2-propen-1-ones（取代 2-羟基查耳酮）的吸收光谱和光化学反应性. 在 5 mM 高氯酸存在下进行紫外线照射后，黄鎓离子以大约 0.34 的高量子产率形成，而与取代基的性质无关。另一方面，在中性溶液中照射时，氨基取代的查尔酮产生光-Z-异构体作为热稳定产物，而大多数其他查尔酮产生环状半缩醛（2-羟基-2-苯基-2H-1-苯并吡喃）。中性溶液中光化学 E/Z 异构化的量子产率与酸溶液中的量子产率相当，除了氨基取代的查耳酮显示较低的量子产率。

  DOI：

  10.1246/bcsj.73.2215
• 作为产物：
  描述：

  二甲氨基苯乙酮 在 氢溴酸 、 溴 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 20.0h， 生成 1-(4-dimethylaminophenyl)-3-(2-hydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  使用 Brønsted 碱/硫脲双功能催化剂对映选择性合成 2,3-二取代反式-2,3-二氢苯并呋喃†

  摘要：

  2,3-二取代的反式-2,3-二氢苯并呋喃衍生物（15个例子，高达96：4 dr，95：5 er）通过分子内迈克尔加成的非对映选择性和对映选择性合成已经使用酮-烯酮底物和双功能叔胺-硫脲催化剂。该方法扩展到包括用于合成 2,3-二取代茚满和 3,4-二取代四氢呋喃衍生物的非活化酮亲核试剂。

  DOI：

  10.1039/c6ob01326k

文献信息

• Primary Processes in Photochromic Reaction of 4-Diethylamino-4′-dimethylamino-2-hydroxychalcone in Toluene
  作者：Kunihiro Tokumura、Naoto Taniguchi、Takashi Kimura、Ryoka Matsushima

  DOI：10.1246/cl.2001.126

  日期：2001.2

  ethylamino-2-hydroxychalcone in toluene, and colored species undergoing dark reaction to regenerate trans-isomer may be ascribed to cis-isomer with the lifetime of 77 min at room temperature. It is demonstrated that a trans→cis isomerization in the lowest triplet state is significantly responsible for the primary process of the coloration.

  发现反式-4-二乙氨基-4'-二甲氨基-2-羟基查尔酮在甲苯中具有光致变色行为，经过暗反应再生反式异构体的有色物质可归因于顺式异构体，室温下寿命为77分钟. 结果表明，最低三重态的反式→顺式异构化是着色的主要过程。
• Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines
  作者：Fedele Manna、Franco Chimenti、Adriana Bolasco、Bruna Bizzarri、Walter Filippelli、Amelia Filippelli、Luigi Gagliardi

  DOI：10.1016/s0223-5234(99)80057-9

  日期：1999.3

  4,6-diaryl and 4,6-aryl-indolyl substituted 3-cyano-2-aminopyridines were synthesized and submitted to evaluation for their anti-inflammatory, analgesic and antipyretic activity. The electronegativity of the substituents and their displacement on the 4- or 6-aryl ring of the 4,6-diaryl-3-cyano-2-aminopyridine nucleus (3a-q) influenced the anti-inflammatory activity which was higher in the presence of electron-realising groups. The introduction of the indol-3-yl substituent in the 4-position of the 3-cyano-2-aminopyridine nucleus (6a-x) increased the anti-inflammatory and analgesic power, but there was no evidence of the relationship among the electronic characteristic of the substituents, their displacement on the 6-phenyl ring and the activity. Conversely, the displacement of the 2-hydroxyphenyl group in the 4-position (4a-e) and of the indol-3-yl group in the 6-position (8h-w) decreased the anti-inflammatory activity. All derivatives did not show any significative antipyretic activity. (C) Elsevier, Paris.
• Hydrolysis of Benzopyrylium Dyes - An Application of the Concept of Chemical Hardness
  作者：Heike Lietz、G�nter Haucke、Peter Czerney、Birgit John

  DOI：10.1002/prac.199633801142

  日期：——

  A systematic study on the relationship between the substitution pattern, the pK(a) values, and spectral properties of flavylium cations and the respective-(CH2)(2)-bridged analoga (5,6-dihydrobenzo[c]xanthylium cations) is given in order to find rules concerning their spectral behaviour and their chemical reactivity.Our results show that the concept of chemical hardness can explain the different reactivity of 4'- and 7'-substituted flavylium ions against HO-. The pK(a) values of these species, which can act as a measure of reactivity with respect to a nucleophile, correlate linearly with the absolute hardness calculated from half the energy gap between the frontier orbitals. Since the longest-wavelength UV/VIS absorption maximum is mainly determined by the HOMO-LUMO transition, an analogous linear correlation is obtained between the spectral 0-0 transition and the pK(a) value. Deviations from these correlations are assumed to be due to steric effects.