6-chloro-4-methyl-2H-chromen-2-one | 24145-78-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-chloro-4-methyl-2H-chromen-2-one
• 英文别名: 4-methyl-6-chlorocoumarin；6-chloro-4-methylcoumarin；2H-1-Benzopyran-2-one, 6-chloro-4-methyl-；6-chloro-4-methylchromen-2-one
• CAS: 24145-78-6
• 化学式: C₁₀H₇ClO₂
• 分子量: 194.617
• InChiKey: QCRDBIMUDSBUAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-4-methyl-2H-chromen-2-one 反应 140.0h， 以50%的产率得到(1R,2S,11S,12R)-5,18-dichloro-1,2-dimethyl-9,14-dioxapentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione
  参考文献：
  名称：

  Photodimerization of coumarins in solid cyclodextrin inclusion complexes

  摘要：

  The photodimerizations of coumarin and eight of its derivatives are found to proceed selectively in solid inclusion complexes with beta- and gamma-cyclodextrins (beta- and gamma-CD). The distribution of photodimers from these complexes is compared with those from the neat coumarin solids and their solutions in a variety of solvents. By assuming that the stereochemistry of the dimers reflects the packing arrangements of their precursors in the CD complexes, several hypotheses concering the locations and arrangements of the coumarins in the host toruses have been made. The stoichiometries of the complexes have been assigned on the basis of the presence or absence of photodimers and from NMR integration ratios of characteristic coumarin and saccharide protons. The relative orientations of substituted coumarins within a complex are inferred from the stereochemistry of the photodimers. Depending upon the substitution pattern of the coumarin molecules and the type of CD employed, complexes whose guest-host stoichiometries are 1:1, 2:1, and 2:2 have been identified. In several instances, dimers not available from irradiation of neat solid coumarins or their solutions have been obtained from the CD complexes.

  DOI：

  10.1021/jo00038a012
• 作为产物：
  描述：

  乙酸-4-氯苯酯 在 三氯化铝 、 sodium acetate 作用下， 生成 6-chloro-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Wittig, Chemische Berichte, 1924, vol. 57, p. 92

  摘要：

  DOI：

文献信息

• [EN] ANTIBACTERIAL COMPOUNDS HAVING BROAD SPECTRUM OF ACTIVITY<br/>[FR] COMPOSÉS ANTIBACTÉRIENS À LARGE SPECTRE D'ACTIVITÉ
  申请人：ACRAF

  公开号：WO2016096686A1

  公开（公告）日：2016-06-23

  The present invention relates to novel antibacterial compounds, pharmaceutical compositions containing them and their use as antimicrobials.

  本发明涉及新型抗菌化合物，含有它们的药物组合物以及它们作为抗微生物药物的用途。
• Coumarins by Direct Annulation: β‐Borylacrylates as Ambiphilic C ₃ ‐Synthons
  作者：Max Wienhold、John J. Molloy、Constantin G. Daniliuc、Ryan Gilmour

  DOI：10.1002/anie.202012099

  日期：2021.1.11

  2‐halo‐phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre‐condition to access 3‐substituted coumarins

  模块化β-硼基丙烯酸酯已被验证为可编程的、两亲性C 3 -合成子，可在2-卤代苯酚衍生物的级联成环中生成结构和电子多样化的香豆素。这种 [3+3] 断开的关键是 BPin 单元，它具有双重用途，既作为 C(sp 2 )–C(sp 2 ) 耦合的无痕连接子，又作为发色团延伸，通过选择性能量转移催化。轻度异构化是获得 3-取代香豆素的先决条件，并提供了分歧的手柄。该方法在含有这种古老化学型的代表性天然产物的合成中得到展示。公开了在 A 环上修饰的 π 扩展雌酮衍生物的简便进入，以证明该方法在生物测定开发或药物再利用中的潜力。
• Ytterbium triflate promoted coupling of phenols and propiolic acids: synthesis of coumarins
  作者：Serena Fiorito、Francesco Epifano、Vito A. Taddeo、Salvatore Genovese

  DOI：10.1016/j.tetlet.2016.05.087

  日期：2016.6

  Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols

  香豆素是众所周知的天然和半合成产品，具有重要的有效药理活性。在这封信中，描述了一种化学合成这类化合物的改进方法。在10％的Yb（OTf）3水合物作为催化剂存在下，在短时间内从微波辐射和无溶剂条件下，短短地从不同取代的酚和丙酸作为起始原料，以良好的产率获得了香豆素。
• Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C–H Activation/Annulation Reactions
  作者：Moisés Gulías、Daniel Marcos-Atanes、José L. Mascareñas、Marc Font

  DOI：10.1021/acs.oprd.9b00191

  日期：2019.8.16

  Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.

  在本文中，我们公开了使用[Cp * RhCl 2 ] 2作为前催化剂和炔烃或一氧化碳作为反应伙伴，从2-烯基苯酚前体组装苯并二氢吡啶和香豆素。使用低催化剂负载量，苯并二氢吡啶和香豆素的制备规模可扩大至33 mmol。
• A single precatalyst tandem RCM–allylic oxidation sequence
  作者：Bernd Schmidt、Stefan Krehl

  DOI：10.1039/c1cc11347j

  日期：——

  Ring closing metathesis of allyloxy styrenes and a subsequent Ru-catalyzed allylic oxidation can be combined to a tandem sequence that makes coumarins accessible using less active but more conveniently available first generation catalysts.

  烯丙氧基苯乙烯的闭环易位反应和随后的Ru催化的烯丙基氧化可以组合成一个串联序列，使香豆素可以使用活性较低但更方便获得的第一代催化剂来获得。