6-chloro-4-hydroxycoumarin | 133406-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-chloro-4-hydroxycoumarin
• 英文别名: 6-chloro-chroman-2,4-dione；6-Chlor-chroman-2,4-dion；6-Chloro-2H-1-benzopyran-2,4(3H)-dione；6-chlorochromene-2,4-dione
• CAS: 133406-30-1
• 化学式: C₉H₅ClO₃
• 分子量: 196.59
• InChiKey: JBXOLMYSNXVWJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-4-hydroxycoumarin 在 sodium hydroxide 、 三氯化铝 作用下， 生成 3-acetyl-6-chloro-chroman-2,4-dione
  参考文献：
  名称：

  Synthese von 4-Oxy-6-chlor-cumarin-derivaten

  摘要：

  DOI：

  10.1002/ardp.19562890307
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium 、 paraffin oil 作用下， 生成 6-chloro-4-hydroxycoumarin
  参考文献：
  名称：

  Synthese von 4-Oxy-6-chlor-cumarin-derivaten

  摘要：

  DOI：

  10.1002/ardp.19562890307

文献信息

• Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C–H Activation
  作者：Yuqin Jiang、Pengfei Li、Jie Zhao、Bingxian Liu、Xingwei Li

  DOI：10.1021/acs.orglett.0c02618

  日期：2020.10.2

  The rhodium(III)-catalyzed coupling of C–H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C–H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol

  铑（III）催化的C–H底物与碘鎓碘化物的偶联已经实现了各种环状骨架的有效合成，其中碘鎓碘化物已被认为是有效且出色的卡宾前体。该反应系统适用于在轻度和氧化还原中性条件下的sp 2和sp 3 C–H底物。在克规模的反应中，催化剂的负载量可以低至0.5mol％。代表性产品在纳摩尔水平下对人癌细胞具有细胞毒性。
• Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[<i>b</i>]naphtho[2,3-<i>d</i>]furan-6,11-dione and First Total Synthesis of Millettocalyxins C and Pongamol Methyl Ether
  作者：Yong Rok Lee、Keon Yong Kang、Gun Joon Lee、Won Kyong Lee

  DOI：10.1055/s-2003-41023

  日期：——

  Ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to vinyl sulfides afforded substituted dihydrofurans with sulfide groups in moderate yields. This new synthetic method has been applied to thesynthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and furanoflavone natural products such as millettocalyxins C and pongol methyl ether.

  Ceric(IV) 硝酸铵介导的 1,3-二羰基与乙烯基硫化物的氧化环加成反应以中等收率提供了具有硫化物基团的取代二氢呋喃。这种新的合成方法已应用于苯并[b]萘并[2,3-d]呋喃-6,11-二酮和呋喃黄酮类天然产物如小米花萼素C、凤梨甲醚的合成。
• Multicomponent Synthesis of 1,3-Diketone-Linked <i>N</i>-Substituted Pyrroles, Pyrrolo[1,2-<i>a</i>]pyrazines, Pyrrolo[1,4]diazepines, and Pyrrolo[1,4]diazocines
  作者：Sivanna Chithanna、Ding-Yah Yang

  DOI：10.1021/acs.joc.8b02819

  日期：2019.2.1

  A new methodology is developed for the efficient synthesis of 1,3-diketone-linked N-substituted pyrroles, pyrrolo[1,2-a]pyrazines, pyrrolo[1,4]diazepines, and pyrrolo[1,4]diazocines in good yields via a Yb(OTf)3-catalyzed, nitromethane-mediated reaction of primary amine/diamine, furfural, and 1,3-diketone. Possible mechanisms for these multicomponent reactions are also proposed.

  开发了一种新方法，可有效合成良好的1,3-二酮连接的N-取代的吡咯，吡咯并[1,2- a ]吡嗪，吡咯并[1,4]二氮杂和吡咯并[1,4]重氮通过Yb（OTf）3催化的，硝基甲烷介导的伯胺/二胺，糠醛和1,3-二酮的反应制备。还提出了这些多组分反应的可能机理。
• UNSYMMETRICALLY SUBSTITUTED 3,3′-METHYLENE BRIDGED 2,2′-DIHYDROXYCHROMONES
  作者：R. A. Abramovitch、J. R. Gear

  DOI：10.1139/v58-221

  日期：1958.11.1

  Unsymmetrically substituted dicoumarol derivatives have been synthesized by taking advantage of the fact that 4-hydroxycoumarins will undergo the Mannich reaction at C₃ and also take part in Michael-type addition reactions. In the presence of methyl iodide, 4-hydroxy-3-N-piperidinomethylcoumarin and 4-hydroxycoumarin gave dicoumarol. By using monosubstituted 4-hydroxycoumarins a variety of unsymmetrically substituted dicoumarols have been prepared in good yield. The infrared spectra of some of the intermediates and products are reported and discussed.

  利用4-羟基香豆素在C3处会发生Mannich反应并参与Michael加成反应的特性，合成了非对称取代的二香豆素衍生物。在甲基碘的存在下，4-羟基-3-N-哌啶甲基香豆素和4-羟基香豆素生成了二香豆素。通过使用单取代的4-羟基香豆素，制备了多种收率良好的非对称取代的二香豆素。报道并讨论了一些中间体和产物的红外光谱。
• BENZOPYRANS AND ANALOGS AS RHO KINASE INHIBITORS
  申请人：Feng Yangbo

  公开号：US20110150833A1

  公开（公告）日：2011-06-23

  Compounds useful as Rho kinase inhibitors of formula (1) wherein the variables are as defined herein are provided. Methods of treatment of malconditions mediated by Rho kinase, and methods of preparation of the compounds, are also provided.

  提供了一些公式（1）中变量的Rho激酶抑制剂，这些化合物可用于治疗由Rho激酶介导的疾病。还提供了制备这些化合物的方法和治疗Rho激酶介导的疾病的方法。