ethyl 4-(4-chlorophenyl)-1-hydroxy-2-naphthoate | 1215856-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 4-(4-chlorophenyl)-1-hydroxy-2-naphthoate
• 英文别名: Ethyl 4-(4-chlorophenyl)-1-hydroxynaphthalene-2-carboxylate；ethyl 4-(4-chlorophenyl)-1-hydroxynaphthalene-2-carboxylate
• CAS: 1215856-70-4
• 化学式: C₁₉H₁₅ClO₃
• 分子量: 326.779
• InChiKey: VASVGCNKIYKKAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-ethyl 3-(2-(4-chlorostyryl)phenyl)-3-oxopropanoate 在 Cl₄Fe 、 苯基氯化硒 作用下， 以 二氯甲烷 为溶剂， 反应 5.05h， 以69%的产率得到ethyl 4-(4-chlorophenyl)-1-hydroxy-2-naphthoate
  参考文献：
  名称：

  硒通过重排介导的联芳基合成

  摘要：

  描述了在路易斯酸存在下使用硒亲电试剂对β-酮酯取代的二苯乙烯衍生物进行的新环化。取代的萘酚是通过环化以及随后在非常温和的反应条件下对芳基进行1,2-重排而获得的。

  DOI：

  10.1021/ol100274e

文献信息

• Bromide-Mediated C–H Bond Functionalization: Intermolecular Annulation of Phenylethanone Derivatives with Alkynes for the Synthesis of 1-Naphthols
  作者：Tao Lu、Ya-Ting Jiang、Feng-Ping Ma、Zi-Jing Tang、Liu Kuang、Yu-Xuan Wang、Bin Wang

  DOI：10.1021/acs.orglett.7b03186

  日期：2017.12.1

  formation of polysubstituted 1-naphthols. The usage of readily available bromine catalyst, broad substrate scope, and mild conditions make this protocol very practical. Mechanistic investigations reveal that the bromination of phenylethanone derivatives occurs to yield bromo-substituted intermediates, which react in situ with alkynes to furnish the desired 1-naphthols.

  已经开发了由溴化物介导的苯乙酮衍生物与炔烃的分子间环化反应，这种反应可以区域选择性地形成多取代的1-萘酚。易于使用的溴催化剂的使用，广泛的底物范围和温和的条件使该方案非常实用。机理研究表明，发生了苯乙酮衍生物的溴化反应，生成了溴取代的中间体，该中间体与炔烃就地反应，生成了所需的1-萘酚。
• Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products
  作者：Gunaganti Naresh、Ruchir Kant、Tadigoppula Narender

  DOI：10.1021/acs.orglett.5b01477

  日期：2015.7.17

  developed for regioselective synthesis of highly substituted α-naphthols, binaphthols, and anthracenol through silver(I) catalyzed C(sp3)–H/C(sp)–H, C(sp2)–H/C(sp)–H functionalization of β-ketoesters and alkynes, respectively, in a single step using water as a solvent. This protocol exhibited broad substrate scope and paved the way for synthesis of anticancer arylnaphthalene lignan natural products such as

  通过银(I)催化的C(sp 3 )–H/C(sp)–H、C(sp 2 )–H/C区域选择性合成高度取代的α-萘酚、联萘酚和蒽酚的新路线已被开发β-酮酯和炔烃的 (sp)–H 官能化，分别在一步中使用水作为溶剂。该方案展示了广泛的底物范围，为合成抗癌芳基萘木脂素天然产物（如diphyllin、taiwanin E和justicidin A）铺平了道路，具有优异的选择性。
• Mn(III)-Mediated Facile Access to Polysubstituted α-Naphthols from β-Keto Ester Derivatives and Terminal Alkynes
  作者：Yuzhu Yang、Weidong Pan、Lisheng He、Fei Li、Xiaolan Liu

  DOI：10.1055/s-0039-1690870

  日期：2020.7

  A novel manganese-mediated reaction for the synthesis of polysubstituted α-naphthols has been developed from β-keto esters and terminal alkynes. This system holds the advantages of readily available starting materials and mild conditions. Mechanistic investigations revealed that this reaction proceeds via a tandem radical cyclization process.

  由β-酮酸酯和末端炔烃开发了一种新型的锰介导的合成多取代α-萘酚的反应。该系统具有容易获得的起始原料和温和条件的优点。机理研究表明，该反应是通过串联自由基环化过程进行的。
• <i>De Novo</i> Synthesis of Polysubstituted Naphthols and Furans Using Photoredox Neutral Coupling of Alkynes with 2-Bromo-1,3-dicarbonyl Compounds
  作者：Heng Jiang、Yuanzheng Cheng、Yan Zhang、Shouyun Yu

  DOI：10.1021/ol402325z

  日期：2013.9.20

  A conceptually new strategy has been described for the mild, practical, and environmentally friendly preparation of naphthols and furans using a visible-light promoted photoredox neutral approach. These reactions between accessible electron-deficient bromides and commercially available alkynes could be carried out at room temperature in good-to-excellent chemical yields without any external stoichiometric oxidants.
• Selenium-Mediated Synthesis of Biaryls through Rearrangement
  作者：Sohail A. Shahzad、Clotilde Vivant、Thomas Wirth

  DOI：10.1021/ol100274e

  日期：2010.3.19

  A new cyclization of β-keto ester substituted stilbene derivatives using selenium electrophiles in the presence of Lewis acids is described. Substituted naphthols are obtained through cyclization and subsequent 1,2-rearrangement of aryl groups under very mild reaction conditions.

  描述了在路易斯酸存在下使用硒亲电试剂对β-酮酯取代的二苯乙烯衍生物进行的新环化。取代的萘酚是通过环化以及随后在非常温和的反应条件下对芳基进行1,2-重排而获得的。