(Z)-4-hydroxy-4-(naphthalen-2-yl)but-3-en-2-one | 62937-29-5

• 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: (Z)-4-hydroxy-4-(naphthalen-2-yl)but-3-en-2-one
• 英文别名: (Z)-4-hydroxy-4-naphthalen-2-ylbut-3-en-2-one
• CAS: 62937-29-5
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: AVPOXVQKZNOHCS-ZSOIEALJSA-N

物化性质

• 熔点：
  72-74 °C
• 沸点：
  419.8±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-hydroxy-4-(naphthalen-2-yl)but-3-en-2-one 、 dimethyl 2-(1-methyl-1H-indol-3-yl)malonate 在 氟硼酸钠 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 11.0h， 以67%的产率得到dimethyl 4-(2-naphthoyl)-3,5-dimethylpyrano[4,3-b]indole-1,1(5H)-dicarboxylate
  参考文献：
  名称：

  基于双氧化[3 + 3]环加成反应的二氢吡喃并[4,3-b]吲哚的电合成。

  摘要：

  氧化性[3 + 3]环加成反应为六元环形成提供了一条有效途径。该方法是基于吲哚/烯胺与活性亚甲基化合物的电化学氧化偶联，然后串联6π-电环化反应生成二氢吡喃并[4,3- b ]吲哚和2,3-二氢呋喃而实现的。阳极氧化产生的自由基与自由基从O 2产生的自由基之间的自由基交叉偶联为合成结构复杂的杂环提供了温和的反应条件。

  DOI：

  10.1002/anie.202003364
• 作为产物：
  描述：

  2,2-dimethyl-6-(2-(naphthalen-2-yl)-2-oxoethyl)-4H-1,3-dioxin-4-one 以 甲苯 为溶剂， 反应 0.5h， 以66%的产率得到4-hydroxy-6-(2-naphthyl)-2H-pyran-2-one
  参考文献：
  名称：

  Facile Syntheses of 2,2-Dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the Corresponding 6-Substituted 4-Hydroxy-2-pyrones

  摘要：

  A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-1. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.

  DOI：

  10.1021/jo050307m

文献信息

• Photo‐Catalyzed Acyl Azolium Promoted Selective <i>α</i>‐C(sp³)−H Acylation of Acetone via HAT: Access to Thermodynamically Less Favoured (<i>Z</i>)‐<i>α,β‐</i>Unsaturated Ketones
  作者：Chandrasekaran Sivaraj、Debabrata Maiti、Thirumanavelan Gandhi

  DOI：10.1002/chem.202303626

  日期：2024.2.21

  Mono α‐acylation of acetone has been achieved for the first time by reacting with bench‐stable acyl azolium salts under violet‐LED light at room temperature. The intermolecular hydrogen atom transfer (HAT) from acetone to triplet state of azolium salts under violet LED irradiation resulted in thermodynamically less favourable (Z)‐α,β‐unsaturated ketones with up to 99 : 1 selectivity via C−C bond formation. This compelling protocol access the desired α‐C(sp³)−H acylation product under metal‐, ligand‐ and oxidant‐free conditions on a wide range of substrates.

  摘要在室温紫外 LED 灯下，通过与台式稳定的酰基唑盐反应，首次实现了丙酮的单α-酰化。在紫光 LED 的照射下，分子间氢原子转移（HAT）从丙酮转移到三重态的偶氮鎓盐，通过 C-C 键的形成产生热力学上较不利的 (Z)-α,β-不饱和酮，其选择性高达 99 ：1 的选择性。在无金属、配体和氧化剂的条件下，这一引人注目的方法可在多种底物上获得所需的α-C(sp3)-H酰化产物。
• Electrosynthesis of Dihydropyrano[4,3‐ <i>b</i> ]indoles Based on a Double Oxidative [3+3] Cycloaddition
  作者：Subin Choi、Jinhwi Park、Eunsoo Yu、Jeongwoo Sim、Cheol‐Min Park

  DOI：10.1002/anie.202003364

  日期：2020.7.13

  methylene compounds followed by tandem 6π‐electrocyclization leading to the synthesis of dihydropyrano[4,3‐b ]indoles and 2,3‐dihydrofurans. The radical–radical cross‐coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.

  氧化性[3 + 3]环加成反应为六元环形成提供了一条有效途径。该方法是基于吲哚/烯胺与活性亚甲基化合物的电化学氧化偶联，然后串联6π-电环化反应生成二氢吡喃并[4,3- b ]吲哚和2,3-二氢呋喃而实现的。阳极氧化产生的自由基与自由基从O 2产生的自由基之间的自由基交叉偶联为合成结构复杂的杂环提供了温和的反应条件。
• Facile Syntheses of 2,2-Dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the Corresponding 6-Substituted 4-Hydroxy-2-pyrones
  作者：Alan R. Katritzky、Zuoquan Wang、Mingyi Wang、C. Dennis Hall、Kazuyuki Suzuki

  DOI：10.1021/jo050307m

  日期：2005.6.1

  A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-1. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.