3-(4-Hydroxyphenyl)pentane-2,4-dione | 163930-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-Hydroxyphenyl)pentane-2,4-dione
• CAS: 163930-36-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: NCUOUCLPMVJYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Hydroxyphenyl)pentane-2,4-dione 在 boron trioxide 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  自组装刚性连接的BF2-姜黄素双发色团的光电特性

  摘要：

  我们描述了双发色分子DA-meso的合成和光谱研究，该分子由两个由刚性二乙炔桥连接的二氟化硼姜黄素 (BF 2 -curcuminoid) 单元组成。这种结构特征赋予了类四极DA-meso在溶液中自组装的强大能力，从而引起光学性质的深刻变化。聚集体的紫外-可见吸收光谱的特点是在低能量下出现红移谱带，其荧光发射发生在近红外（λ max = 700 nm），量子产率低（5%）。这与考虑到 Frenkel 激子模型的 J 聚集体预期的强发射相矛盾。从依赖于浓度的紫外-可见吸收光谱，我们证明了由四个 BF 2 -姜黄素单元组成的二聚体的形成。基于密度泛函理论 (DFT) 的单晶 X 射线衍射结构分析和深入的量子化学计算以及随后在非绝热基础上对电子激发态的分解能够讨论DA-meso的几何形状二聚体，并建立与未受干扰的单色团能量接近的激发态的存在，这是经典的弗伦克尔激子模型无法预测的。研究了以两个和最多四个发色团的

  DOI：

  10.1016/j.dyepig.2022.110677
• 作为产物：
  描述：

  3-<4-(Benzyloxy)phenyl>pentane-2,4-dione 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 3-(4-Hydroxyphenyl)pentane-2,4-dione
  参考文献：
  名称：

  On the Parity in Helical Twisting Power of Ru(III) 1,3-Diketonates of C₂ Symmetry in Nematic Liquid Crystals

  摘要：

  It is demonstrated that the sign of helical twisting power (HTP) of an enantiomeric Ru(III) complex of type [Ru(acac)(2)L] can be switched by choosing L from either L-per or L-para, which is elongated either perpendicular or parallel to the C-2 symmetry axis, and four states become available in combination with Delta Lambda-chirality of the metal center. Complexes 1-n, in which 4,4'-dialkoxylated dibenzoylmethanate ligands are used as L-per, and 2 having L-para = 3-(4'-decyloxyphenyl)pentane-2,4-dionate ligand were prepared for this purpose. They were optically resolved into the enantiomers by means of a clay column chromatography, and their performance as chiral dopants was evaluated in nematic liquid crystals including a room-temperature system, N-methoxybenzylidene-4-n-butylaniline (MBBA), which allowed facile measurements of the helical pitch lengths and CID spectra in the induced chiral nematic states. The induced CID signals have provided a clear evidence for the helical inversion between the two structure types, 1 and 2, of the same chirality. The twisting power of these six-coordinate metal complexes and their structure versus twist sense correlations are interpreted by the shape model. Intrinsically high HTP of Delta-[Ru(acac)(2)L-per] has also allowed for observation of the pitch band due to the selective reflection in the visible wavelength range at the doping level of 2 mol % in MBBA.

  DOI：

  10.1021/ja042549u

文献信息

• An Efficient and Mild CuI/<scp>l</scp>-Proline-Catalyzed Arylation of Acetylacetone or Ethyl Cyanoacetate
  作者：Yongwen Jiang、Nan Wu、Haihong Wu、Mingyuan He

  DOI：10.1055/s-2005-918921

  日期：——

  The coupling reaction of aryl iodides with acetylacetone or ethyl cyanoacetate under catalysis of CuI/l-proline works at ­relatively mild conditions to provide 3-aryl-2, 4-pentanediones and α-aryl cyanoacetates in moderate to good yields.

  在CuI/l-脯氨酸催化下，芳基碘化物与乙酰乙酮或乙基氰乙酸酯的偶联反应在相对温和的条件下进行，能够生成3-芳基-2, 4-戊二酮和α-芳基氰乙酸酯，产率中等至良好。
• Assessing and utilizing esterase specificity in antimicrobial prodrug development
  作者：Kenton J. Hetrick、Ronald T. Raines

  DOI：10.1016/bs.mie.2021.11.008

  日期：——

  enzymes, esterases have been investigated for decades and have found use in industrial processes, synthetic organic chemistry, and elsewhere. Esters are functional groups composed of an alcohol moiety and a carboxylic acid moiety. Although much work has explored the influence of the carboxyl moiety of an ester on its susceptibility to esterases, little work has explored the influence of the alcohol moiety

  作为一类酶，酯酶已被研究了数十年，并已在工业过程、合成有机化学和其他领域中得到应用。酯是由醇部分和羧酸部分组成的官能团。尽管很多工作已经探索了酯的羧基部分对其酯酶敏感性的影响，但很少有研究探索醇部分的影响。在这里，我们描述了一种体外方法来探索改变酯的醇部分对其酶水解的影响，包括分析这些数据的策略。然后，我们描述了利用来自这些测定的数据来开发靶向抗菌前药，由于物种特异性酯酶的区分活性，这些前药在某些物种中激活。我们设想基因组学和机器学习的潜力可以进一步推动这些努力。最后，我们预计这些想法在未来的潜在用途，包括开发有针对性的抗癌化合物。
• Synthesis of 3-Substituted Pentane-2,4-Diones: Valuable Intermediates For Liquid Crystals
  作者：Carlos Cativiela、Jose L. Serrano、Maria M. Zurbano

  DOI：10.1021/jo00115a023

  日期：1995.5

  General procedures for the synthesis of six series of 3-substituted pentane-2,4-diones are described. The diones mere used as intermediates in the preparation of pyrazoles, isoxazoles, and coordination complexes whose mesogenic properties have been studied. Nematic and smectic phases have been obtained in a number of cases, and the relationship between molecular structure and mesogenic properties has been explored.
• On the Parity in Helical Twisting Power of Ru(III) 1,3-Diketonates of <i>C</i>₂ Symmetry in Nematic Liquid Crystals
  作者：Jun Yoshida、Hisako Sato、Akihiko Yamagishi、Naomi Hoshino

  DOI：10.1021/ja042549u

  日期：2005.6.1

  It is demonstrated that the sign of helical twisting power (HTP) of an enantiomeric Ru(III) complex of type [Ru(acac)(2)L] can be switched by choosing L from either L-per or L-para, which is elongated either perpendicular or parallel to the C-2 symmetry axis, and four states become available in combination with Delta Lambda-chirality of the metal center. Complexes 1-n, in which 4,4'-dialkoxylated dibenzoylmethanate ligands are used as L-per, and 2 having L-para = 3-(4'-decyloxyphenyl)pentane-2,4-dionate ligand were prepared for this purpose. They were optically resolved into the enantiomers by means of a clay column chromatography, and their performance as chiral dopants was evaluated in nematic liquid crystals including a room-temperature system, N-methoxybenzylidene-4-n-butylaniline (MBBA), which allowed facile measurements of the helical pitch lengths and CID spectra in the induced chiral nematic states. The induced CID signals have provided a clear evidence for the helical inversion between the two structure types, 1 and 2, of the same chirality. The twisting power of these six-coordinate metal complexes and their structure versus twist sense correlations are interpreted by the shape model. Intrinsically high HTP of Delta-[Ru(acac)(2)L-per] has also allowed for observation of the pitch band due to the selective reflection in the visible wavelength range at the doping level of 2 mol % in MBBA.
• Optoelectronic properties of a self-assembling rigidly-linked BF2-curcuminoid bichromophore
  作者：Claire Tonnelé、Manon Catherin、Michel Giorgi、Gabriel Canard、David Casanova、Frédéric Castet、Elena Zaborova、Frédéric Fages

  DOI：10.1016/j.dyepig.2022.110677

  日期：2022.11

  the bichromophoric molecule DA-meso consisting of two boron difluoride curcuminoid (BF2-curcuminoid) units tethered by the rigid diacetylenic bridge. This structural feature imparts the quadrupolar-like DA-meso with a strong ability to self-assemble in solution, which induces a profound change in the optical properties. The UV–vis absorption spectrum of the aggregate is characterized by the appearance

  我们描述了双发色分子DA-meso的合成和光谱研究，该分子由两个由刚性二乙炔桥连接的二氟化硼姜黄素 (BF 2 -curcuminoid) 单元组成。这种结构特征赋予了类四极DA-meso在溶液中自组装的强大能力，从而引起光学性质的深刻变化。聚集体的紫外-可见吸收光谱的特点是在低能量下出现红移谱带，其荧光发射发生在近红外（λ max = 700 nm），量子产率低（5%）。这与考虑到 Frenkel 激子模型的 J 聚集体预期的强发射相矛盾。从依赖于浓度的紫外-可见吸收光谱，我们证明了由四个 BF 2 -姜黄素单元组成的二聚体的形成。基于密度泛函理论 (DFT) 的单晶 X 射线衍射结构分析和深入的量子化学计算以及随后在非绝热基础上对电子激发态的分解能够讨论DA-meso的几何形状二聚体，并建立与未受干扰的单色团能量接近的激发态的存在，这是经典的弗伦克尔激子模型无法预测的。研究了以两个和最多四个发色团的