3-Naphthalen-1-yl-1-pyridin-2-ylprop-2-en-1-one | 909768-11-2

• 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: 3-Naphthalen-1-yl-1-pyridin-2-ylprop-2-en-1-one
• CAS: 909768-11-2
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: AAVWDHRTGKVFBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Naphthalen-1-yl-1-pyridin-2-ylprop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Novel 2-pyrazoline derivatives as potential anticonvulsant agents

  摘要：

  A series of new 2-pyrazoline derivatives has been synthesized by reacting 3-(substituted-phenyl)-1-pyridin-2-yl-propenones using two routes one using thiosemicarbazide and the other by hydrazine hydrate. The chemical structures were established by IR, Mass, H-1-NMR, C-13-NMR spectroscopic data, and elemental analysis. The anticonvulsant activity of the synthesized compounds was evaluated by the "maximal electroshock seizure" (MES) test and pentylenetetrazole (PTZ) test using male albino mice. Compounds 2e, 5-(naphthalene-1-yl)-3-(pyridine-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioic acid amide, and 3c, N-ethyl-5-(naphthalene-1-yl)-3-(pyridine-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide showed appreciable activity in the MES as well as PTZ test at all the evaluated doses.

  DOI：

  10.1007/s00044-013-0530-7
• 作为产物：
  描述：

  2-乙酰基吡啶 、 1-萘甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以80 %的产率得到3-Naphthalen-1-yl-1-pyridin-2-ylprop-2-en-1-one
  参考文献：
  名称：

  高效可回收新型纺锤体Fe2O3@SiO2/In2O3纳米磁性催化剂设计用于偶氮甲碱化合物的绿色合成

  摘要：

  一种新型可重复使用的纳米磁性催化剂 Fe 2 O 3 @SiO 2 /In 2 O 3是通过简单的化学方法分三个连续步骤合成的。通过 FT-IR、XRD、SEM、EDX、TEM 和 VSM 对纳米催化剂进行了表征。XRD 图显示 Fe 2 O 3和 SiO 2的特征峰，伴随着分配给 In 2 O 3不同平面的新峰，证实了 In 2 O 3在 Fe 2 O 3 @SiO 2表面上的形成芯/壳纺锤体。TEM照片显示Fe 2 O 3的纺锤状颗粒被SiO 2壳覆盖，平均直径为20nm的In 2 O 3纳米颗粒悬浮在Fe 2 O 3 @SiO 2表面。纳米磁性催化剂 Fe 2 O 3 @SiO 2 /In 2 O 3用于将 (4-nitrophenyl)-1-phenyl-1H-pyrazole-5-amine 和查耳酮衍生物转化为有价值的偶氮甲碱化合物 3 -(取代)-1-(吡啶-2-基)烯丙基)-3-(4-硝基苯基)-1-苯基-1H

  DOI：

  10.1007/s11164-022-04894-4

文献信息

• PCN Pincer Palladium(II) Complex Catalyzed Enantioselective Hydrophosphination of Enones: Synthesis of Pyridine-Functionalized Chiral Phosphine Oxides as NC_sp³O Pincer Preligands
  作者：Xin-Qi Hao、Juan-Juan Huang、Tao Wang、Jing Lv、Jun-Fang Gong、Mao-Ping Song

  DOI：10.1021/jo5015307

  日期：2014.10.17

  A series of chiral PCN pincer Pd(II) complexes VI–XIII with aryl-based aminophosphine–imidazoline or phosphinite–imidazoline ligands were synthesized and characterized. They were examined as enantioselective catalysts for the hydrophosphination of enones. Among them, complex IX, which features a Ph2PO donor as well as an imidazoline donor with (4S)-phenyl and N-Tol-p groups, was found to be the optimal

  合成并表征了一系列具有芳基氨基膦-咪唑啉或次膦酸酯-咪唑啉配体的手性PCN夹心Pd（II）配合物VI - XIII。他们被检查为烯酮氢磷酸化的对映选择性催化剂。其中，具有Ph 2 PO供体以及具有（4S）-苯基和N- Tol- p基团的咪唑啉供体的配合物IX被认为是最佳催化剂。因此，在2–5 mol％的络合物IX存在下各种各样的烯酮与二芳基膦平稳地反应，以高收率得到对映体选择性高达98％ee的相应手性膦衍生物。尤其是，对于Pd中心具有强配位能力的杂芳基物质，例如含2-噻吩基，2-呋喃基和2-吡啶基的烯酮，也是当前催化体系的合适底物。例如，用二苯基膦将2-烯酰基吡啶进行氢磷酸化，然后用H 2 O 2氧化以高收率得到具有良好或优异的对映选择性的相应的吡啶官能化的手性氧化膦（10个实施例，至多95％ee）。此外，已经证明，所获得的含吡啶的氧化膦在与PdCl 2的反应中作为三齿配体，通过C sp 3
• Highly enantioselective synthesis of naphthoquinones and pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides
  作者：Nagaraju Molleti、Vinod K. Singh

  DOI：10.1039/c5ob00105f

  日期：——

  bis-squaramide catalyzed conjugate addition of 2-hydroxy-1,4-naphthoquinone to 2-enoylpyridines. Some of the Michael products have been successfully converted into various enantioenriched pyranonaphthoquinone derivatives. The protocol is further extended to the synthesis of various 4-hydroxycoumarin derivatives under mild conditions.

  使用2-羟基-1,4-萘醌双官能手性双-方酸催化的共轭加成反应到2-烯丙基吡啶中，已高收率和优异的对映选择性（高达> 99％ee）合成了多种对映体富集的萘醌。Michael的某些产品已成功转化为各种对映体富集的吡喃并萘醌衍生物。该方案进一步扩展到在温和条件下合成各种4-羟基香豆素衍生物。
• Diastereo- and enantioselective direct vinylogous Michael addition of γ-substituted butenolides to 2-enoylpyridines catalyzed by chiral bifunctional amine-squaramides
  作者：Zhen-Hua Wang、Zhi-Jun Wu、Xue-Qun Huang、Deng-Feng Yue、Yong You、Xiao-Ying Xu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1039/c5cc06383c

  日期：——

  The diastereo- and enantioselective direct vinylogous Michael addition reaction of [gamma]-substituted butenolides to 2-enoylpyridines has been achieved. A range of [gamma],[gamma]-disubstituted butenolide derivatives, bearing two consecutive tri- and tetrasubstituted stereogenic...

  已经实现了γ-取代的丁烯内酯对2-烯丙基吡啶的非对映和对映选择性的直接乙烯基乙烯基迈克尔加成反应。一系列具有两个连续的三和四取代的立体异构...的γ，γ-二取代的丁烯内酯衍生物
• Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines
  作者：Zhen-Hua Wang、Zhi-Jun Wu、Deng-Feng Yue、Yong You、Xiao-Ying Xu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1039/c6ob01191h

  日期：——

  organocatalyzed direct asymmetric vinylogous Michael addition reaction of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines has been developed with a chiral bifunctional amine-squaramide as the catalyst. This approach provides easy access to a series of optically active α,β-unsaturated γ-substituted butyrolactams in high yields (up to 99%) with excellent diastereoselectivities (up to >99 : 1) and enantioselectivities

  已经开发了以手性双官能胺-方酸酰胺为催化剂的α，β-不饱和γ-丁内酰胺对2-烯丙基吡啶的有机催化直接不对称乙烯基类迈克尔迈克尔加成反应。这种方法可轻松获得一系列具有高非对映选择性（高达> 99：1）和对映选择性（高达ee> 99％）的高产率（高达99％）的光学旋光性α，β-不饱和γ-取代的丁内酰胺。 。
• Asymmetric Catalysis of Diels-Alder Cycloaddition of 2-Alkenoyl Pyridine with Cyclopentadiene by Binaphthol-Titanium Complex
  作者：Li Wang、Ji Zhang、Na Wang、Xin-Bin Yang、Qin Wang、Xiao-Qi Yu

  DOI：10.2174/157017809788681419

  日期：2009.7.1

  Asymmetric Diels-Alder reactions between aza-chalcone and cyclopentadiene (CP) catalyzed by the binaphthol-titanium (BINOL – Ti) in the presence of HMPA (80 mole %) were studied. The products were obtained with up to 87% ees.

  研究了在HMPA（80摩尔％）存在下联萘酚钛（BINOL-Ti）催化的氮杂查尔酮与环戊二烯（CP）之间的不对称Diels-Alder反应。获得的产品具有高达87％的ee。