3-(9-anthryl)-1-phenylprop-2-en-1-one | 19738-94-4

• 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: 3-(9-anthryl)-1-phenylprop-2-en-1-one
• 英文别名: 3-(9-anthryl)-1-phenyl-2-propen-1-one；APPO；9-(2-Benzoyl-vinyl)-anthracen；3-(anthracen-9-yl)-1-phenylprop-2-en-1-one；3-anthracen-9-yl-1-phenyl-prop-2-enone；3-anthracen-9-yl-1-phenyl-propenone；3-[9]anthryl-1-phenyl-propenone；3-[9]Anthryl-1-phenyl-propenon；APO；1-(9-Anthryl)-2-benzoylethylene；3-anthracen-9-yl-1-phenylprop-2-en-1-one
• CAS: 19738-94-4
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: HTNKWVPCJOMMPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  121 °C(Solv: ethanol (64-17-5))
• 沸点：
  525.7±33.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(9-anthryl)-1-phenylprop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 以77%的产率得到3-anthracen-9-yl-5-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation

  摘要：

  In an effort to develop selective MAO (monoamine oxidase) B inhibitors, structure based virtual screening was initiated on an in-house library. Top 10 HITS were synthesized and evaluated for MAO (A and B) inhibitory activity, both against human and rat enzymes. All the compounds were found selective, reversible and active in nM range (100 times more potent than selegeline) towards MAO-B. Outstanding co-relation between predicted and experimental K(i) values were observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.030
• 作为产物：
  描述：

  蒽 在 乙酸乙酯 、 三氯氧磷 作用下， 生成 3-(9-anthryl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  The Constitution of Natural Tannins. VIII. Coloring Matters Derived from Anthracene-9-aldehyde

  摘要：

  DOI：

  10.1021/ja01257a027

文献信息

• Uncatalyzed conjugate addition of organozinc halides to enones in DME: a combined experimental/computational study on the role of the solvent and the reaction mechanism
  作者：Gianluca Casotti、Gianluca Ciancaleoni、Filippo Lipparini、Chiara Nieri、Anna Iuliano

  DOI：10.1039/c9sc04820k

  日期：——

  calculations, prompted by the experimental aggregation study, revealed an unexpected reaction mechanism, where the coordinating capabilities of DME stabilize a transition state involving two organozinc moieties, lowering the activation energy of the reaction with respect to that seen for THF, enough to explain the fast and quantitative reactions observed experimentally and the different behaviors of

  如果使用 DME 代替 THF 作为溶剂，则在 LiCl 存在下通过将锌直接插入有机卤化物中制备的芳基卤化锌和烷基卤化锌均以优异的收率与非烯醇化不饱和酮发生共轭加成反应。扩散核磁共振测量表明，在合成过程中使用的实验条件下，该物质经历了相当大的聚集，但在两种溶剂之间没有发现实质性差异。由实验聚集研究推动的密度泛函理论计算揭示了一种意想不到的反应机制，其中 DME 的配位能力稳定了涉及两个有机锌部分的过渡态，相对于 THF，降低了反应的活化能，
• Imidazolium-based chiral ionic liquids: synthesis and application
  作者：Yumiko Suzuki、Junichiro Wakatsuki、Mariko Tsubaki、Masayuki Sato

  DOI：10.1016/j.tet.2013.09.017

  日期：2013.11

  centers on N-substituents is reported. [(2S,3S)-2,3-Dihydroxybutane-1,4-bis(3-butylimidazolium)]-[bis(trifluoromethanesulfonyl)amide]2 and [(4S,5S)-2-phenyl-1,3-dioxolane-4,5-bis(1-methylimidazolium)]-[bis(trifluoromethanesulfonyl)amide]2 induced enantioselectivity in the Michael addition of malonic esters to chalcones.

  的含有咪唑核和手性中心的手性离子液体的合成ñ -取代基被报告。[（2小号，3小号）-2,3- Dihydroxybutane -1,4-双（3-丁基咪唑）] - [双（三氟甲磺酰）酰胺] 2和[（4-小号，5小号）-2-苯基-1- 1,3-二氧戊环-4,5-二（1-甲基咪唑）] - [双（三氟甲磺酰）酰胺] 2在迈克尔加成丙二酸酯的查耳酮向诱导对映选择性。
• Highly Diastereo- and Enantioselective Cross-Cascade Reactions of Different Enones
  作者：Huicai Huang、Wenbin Wu、Kailong Zhu、Juan Hu、Jinxing Ye

  DOI：10.1002/chem.201204520

  日期：2013.3.18

  Cascading ketones! The first highly efficient asymmetric cross‐cascade reaction of different α,β‐unsaturated ketones catalyzed by an easily prepared bulky primary amine salt has been developed. It affords the corresponding diverse products containing three to four contiguous stereocenters with excellent enantio‐ and diastereoselectivities (see scheme).

  级联的酮！已经开发出了第一个高效的不对称交叉级联反应，该反应由容易制备的笨重的伯胺盐催化，具有不同的α，β-不饱和酮。它提供相应的多样化产品，其中包含三到四个连续的立体中心，具有出色的对映异构和非对映异构选择性（请参见方案）。
• Anchoring pyrazolines on a 2,2′:6′,2″-terpyridine backbone
  作者：E Liu、Li Li、Hangxing Xiong、Corinna Chan、Jessica Cheng、Guoqi Zhang

  DOI：10.1016/j.molstruc.2017.07.057

  日期：2017.11

  pyrazoline derivatives into the classical 2,2′:6′,2″-terpyridine (2,2′:6′,2″-tpy) backbone leads to the synthesis of a new class of compounds, 4′-pyrazolinyl-2,2′:6′,2″-tpys. Six such derivatives bearing differently substituted pyrazolines have been synthesized with a facile two-step procedure using simple chalcone compounds and 4′-hydrazino-2,2′:6′,2″-tpy as starting materials, and they were fully characterized

  摘要 将吡唑啉衍生物引入经典的 2,2':6',2"-三联吡啶 (2,2':6',2"-tpy) 骨架导致合成一类新化合物，4'-吡唑啉基- 2,2':6',2"-tpys。使用简单的查耳酮化合物和 4'-hydrazino-2,2':6',2"-tpy 作为起始原料，通过简单的两步法合成了六种带有不同取代吡唑啉的衍生物，并通过红外光谱对其进行了充分表征、核磁共振、质谱和元素分析。两种代表性的晶体结构已通过单晶 X 射线衍射分析确定。固态结构表明在这些化合物的每一个中都存在两种对映异构体作为外消旋物，并且在 tpy 和吡唑啉域中的芳环之间的排列会受到取代基的影响。分子间堆积主要由芳族区域之间的 π 堆积相互作用驱动。还研究了新化合物的溶液电子吸收和发射行为。
• Application of Polyphosphoric Acid‐Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2‐Acylpyrroles from Chalcones
  作者：Togiti Uday Kumar、Yadagiri Thigulla、Krishnan Rangan、Anupam Bhattacharya

  DOI：10.1002/jhet.3494

  日期：2019.4

  approach for the synthesis of 2‐acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4‐substituted‐3‐acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid‐mediated acyl rearrangement

  本文报道了一种无金属合成2-酰基吡咯的方法。目标分子的合成从查耳酮开始，分两个步骤进行。第一步涉及通过与TosMIC反应将查尔酮转化为相应的4-取代3-酰基吡咯。在随后的步骤中，通过多磷酸介导的3酰基吡咯的酰基重排为其2酰基同类物，以中等至高收率获得了目标分子。至关重要的最后一步是在吡咯环上进行各种取代。初步的机制确定实验表明了lium离子的参与。