(E)-4-(naphthalene-2-yl)but-3-en-2-one | 51557-10-9

• 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: (E)-4-(naphthalene-2-yl)but-3-en-2-one
• 英文别名: (E)-4-(naphthalen-2-yl)but-3-en-2-one；(E)-4-(2-Naphthyl)-but-3-en-2-one；(E)-4-naphthalen-2-ylbut-3-en-2-one
• CAS: 51557-10-9
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: ANSMNUDVLLXIEM-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 储存条件：
  存储在室温下

反应信息

• 作为反应物：
  描述：

  (E)-4-(naphthalene-2-yl)but-3-en-2-one 在 盐酸肼 、 水 、 sodium ethanolate 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 11.0h， 生成 3-(1-(4-fluorobenzyl)-4-(naphthalen-2-yl)-1H-pyrrol-3-yl)-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Pyrrolyl Pyrazoles as Non-Diketo Acid Inhibitors of the HIV-1 Ribonuclease H Function of Reverse Transcriptase

  摘要：

  Due to the biological liability of diketo acid (DKA) chain, we transferred this element of our previously reported anti-HIV-1 pyrrolyl derivatives to a non-DKA scaffold, obtaining a series of pyrrolyl-pyrazole carboxylic acids as new RNase H inhibitors. Among the newly synthesized derivatives, oxyphenyl-pyrrolyl-pyrazoles demonstrated inhibitory activities within the low micromolar/submicromolar range with compound 11b being the most potent. Interestingly, all tested compounds showed up to 2 orders of magnitude of selectivity for RNase H vs integrase. Docking studies within the RNase H catalytic site, coupled with site-directed mutagenesis, showed the key structural features that could confer the ability to establish specific interactions within RNase H. Furthermore, they proved the ability of our compounds to interact with amino acids highly conserved among HIV-1 subspecies isolated among patients carrying drug-resistant variants. In the end, the newly discovered pyrazole carboxylic acid derivatives feature promising serum stability with respect to their corresponding DKAs.

  DOI：

  10.1021/acsmedchemlett.9b00617
• 作为产物：
  描述：

  1-甲氧基-4-((E)-苯乙烯基)-苯 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 57.0h， 以96%的产率得到(E)-4-(naphthalene-2-yl)but-3-en-2-one
  参考文献：
  名称：

  质子辅助的直接照射带来的二苯乙烯类似物反应路径的转换。

  摘要：

  通过调节盐酸的浓度，可以完全切换二苯乙烯类似物（1a-1d）直接照射过程中的光化学反应途径。竞争性的开环和酸催化的水解过程是这种新型选择性的原因。

  DOI：

  10.1021/ol006917k

文献信息

• Design, synthesis and biological evaluation of novel C3-functionalized oxindoles as potential Pim-1 kinase inhibitors
  作者：Hong-bao Sun、Xiao-yan Wang、Guo-bo Li、Li-dan Zhang、Jie Liu、Li-feng Zhao

  DOI：10.1039/c5ra00177c

  日期：——

  A novel series of C3-functionalized oxindoles, 3-(2-oxo-4-phenylbut-3-en-1-ylidene) indolin-2-ones as potential Pim-1 kinase inhibitors, were designed, synthesized and investigated for inhibition of human cancer-cell proliferation.

  一系列新型的C3-功能化氧吲哚，3-(2-氧代-4-苯基丁-3-烯-1-基亚甲基)吲哚啉-2-酮作为潜在的Pim-1激酶抑制剂被设计、合成并用于研究抑制人类癌细胞增殖。
• Copper catalyzed oxygen assisted C(CNOH)–C(alkyl) bond cleavage: a facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids
  作者：Pochampalli Sathyanarayana、Owk Ravi、Prathap Reddy Muktapuram、Surendar Reddy Bathula

  DOI：10.1039/c5ob01569c

  日期：——

  A novel copper-catalyzed aerobic oxidative C(NOH)–C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.

  描述了一种新型的铜催化的芳基/芳烷基/乙烯基酮的需氧氧化C（NOH）-C（烷基）键裂解反应，用于合成芳族/丙烯酸。可以选择性地裂解在一端具有芳基/芳烷基/乙烯基而在另一端具有甲基至任何高级烷基的一系列酮，并通过肟中间体将其转化为相应的酸。
• Asymmetric 1,2-Reduction of Enones with Potassium Borohydride Catalyzed by Chiral <i>N,N</i>′-Dioxide–Scandium(III) Complexes
  作者：Peng He、Xiaohua Liu、Haifeng Zheng、Wei Li、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol302430h

  日期：2012.10.5

  The first catalytic enantioselective 1,2-reduction of enones with 0.45 mol equiv potassium borohydride solution catalyzed by a chiral N,N′-dioxide–Sc(III) complex catalyst was accomplished under mild reaction conditions. A number of optically active allylic alcohols were obtained in good to excellent enantioselectivities (up to 95% ee) with nearly quantitative yields.

  在温和的反应条件下，用手性N，N'-二氧化物-Sc（III）络合物催化剂催化的0.45摩尔当量硼氢化钾溶液对烯酮的首次催化对映选择性1,2-还原。以接近定量的产率获得了许多具有良好至优异对映选择性（高达95％ee）的旋光烯丙基醇。
• Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction
  作者：Bedřich Formánek、Jiří Tauchman、Ivana Císařová、Jan Veselý

  DOI：10.1021/acs.joc.0c00882

  日期：2020.7.2

  derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.

  本报告描述了在金鸡纳生物碱胺存在下2-亚烷基苯并[ b ]噻吩酮衍生物与烯酮之间的有机催化级联反应。通过一步合成，制备了包含三个立体中心的螺苯并噻吩苯甲酸环己烷衍生物，其产率为88％至96％，对映选择性（对映体过量（ee））为85至97％，非对映选择性约为14/2/1。因此，该方法为合成新型的光学活性的2-螺苯并噻吩酮提供了有效的途径。
• PPh₃⋅HBr-DMSO Mediated Expedient Synthesis of γ-Substituted β,γ-Unsaturated α-Ketomethylthioesters and α-Bromo Enals: Application to the Synthesis of 2-Methylsulfanyl-3(<i>2 H</i>)-furanones
  作者：Kanchan Mal、Abhinandan Sharma、Prakas R. Maulik、Indrajit Das

  DOI：10.1002/chem.201303755

  日期：2014.1.13

  An efficient chemoselective general procedure for the synthesis of γ‐substituted β,γ‐unsaturated α‐ketomethylthioesters from α,β‐unsaturated ketones has been achieved through an unprecedented PPh3⋅HBr‐DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α‐bromoenals from enals. Furthermore, AuCl3‐catalyzed efficient

  对于γ-β取代的合成的高效化学选择性一般方法，从α，β不饱和酮γ不饱和α-ketomethylthioesters已经通过了前所未有的PPH实现3 ⋅HBr-DMSO介导的氧化溴化和kornblum氧化反应序列。新开发的试剂系统可用于从enals合成α-溴烯醛。此外，还描述了AuCl 3催化在极温和条件下从上述中间体有效地获得3（2H）-呋喃酮的方法。