6-hydroxy-7-methyl-4-(chloromethyl)-2H-chromen-2-one

• 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-hydroxy-7-methyl-4-(chloromethyl)-2H-chromen-2-one
• 英文别名: 4-chloromethyl-6-hydroxy-7-methylcoumarin；4-(chloromethyl)-6-hydroxy-7-methylchromen-2-one
• 化学式: C₁₁H₉ClO₃
• mdl: MFCD04167233
• 分子量: 224.644
• InChiKey: QJKVIXRACLBRAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-7-methyl-4-(chloromethyl)-2H-chromen-2-one 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-amino-4,6-dimethylthieno[2,3-b]pyridin-2-yl)-6-hydroxy-7-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and properties of 4-(3-aminothieno-[2,3-b]pyridin-2-yl)coumarins

  摘要：

  Substituted 4-[(3-cyanopyridin-2-yl)thiomethyl]coumarins have been synthesized by the alkylation of 2-mercapto-4,6-dimethylnicotinonitrile with 4-chloromethylcoumarins. Substituted 4-(3-amino-thieno[2,3-b]pyridin-2-yl)coumarins have been obtained by a subsequent intramolecular condensation of the methylene and cyano groups. 6H-Chromeno[4,3-d]thieno[3,2-b:5,4-b']dipyridin-6-ones were isolated as a result of the interaction of these compounds with aldehydes, and their aminomethyl derivatives were synthesized.

  DOI：

  10.1007/s10593-012-1083-2
• 作为产物：
  描述：

  甲基氢醌 、 alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 6-hydroxy-7-methyl-4-(chloromethyl)-2H-chromen-2-one
  参考文献：
  名称：

  香豆素-4-基甲基膦酸的合成

  摘要：

  合成了新的香豆素-4-基甲基膦酸酯和香豆素-4-基甲基膦酸并测试了抗病毒活性。

  DOI：

  10.1007/s10600-019-02766-9

文献信息

• Synthesis of 4-aminomethyl analogs of daphnetin
  作者：A. V. Levenets、M. S. Frasinyuk、V. P. Khilya

  DOI：10.1007/s10600-007-0183-1

  日期：2007.9

  4-Aminomethyl analogs of the natural coumarin daphnetin were synthesized. The reaction of 4-chloromethyl-coumarins with aliphatic and aromatic amines was studied.

  合成了天然香豆素达夫宁的4-氨甲基类似物。研究了4-氯甲基香豆素与脂肪族和芳香族胺的反应。
• Synthesis of cytisine derivatives of coumarins
  作者：M. S. Frasinyuk、V. I. Vinogradova、S. P. Bondarenko、V. P. Khilya

  DOI：10.1007/s10600-007-0198-7

  日期：2007.9

  New substituted 4-chloromethylcoumarins that were used as alkylating agents to modify cytisine were synthesized by Pechmann condensation. A series of 4-(12-cytisylmethyl)coumarins containing pharmacophores of the natural heterocycles coumarin and cytisine in a single molecule was prepared. The alkylation gave the best results if diisopropylethylamine was used as the base.

  通过Pechmann缩合合成了新的取代4-氯甲基香豆素作为烷基化剂来修饰金雀花碱。制备了一系列在单分子中含有天然杂环香豆素和金雀花碱药效基团的4-(12-金雀花基甲基)香豆素。如果使用二异丙基乙胺作为碱，则烷基化得到最好的结果。
• Synthesis and properties of 4-chloromethyl-6-hydroxy-coumarins and 4-(2-benzofuryl)-6-hydroxycoumarins
  作者：M. S. Frasinyuk、S. P. Bondarenko、V. P. Khilya

  DOI：10.1007/s10593-009-0275-x

  日期：2009.3

  4-chloromethyl-6-hydroxycoumarins have been obtained by the condensation of hydroquinone derivatives with 4-chloroacetoacetic ester, and have been used for the synthesis of 4-(2-benzofuryl)-6-hydroxycoumarins. Alkylation and acylation of the phenolic hydroxyl of the synthesized 4-(2-benzo-furyl)coumarins have been investigated.

  通过氢醌衍生物与4-氯乙酰乙酸酯的缩合反应获得了新的4-氯甲基-6-羟基香豆素，并将其用于合成4-（2-苯并呋喃基）-6-羟基香豆素。已经研究了合成的4-（2-苯并呋喃基）香豆素的酚羟基的烷基化和酰化。
• Synthesis and properties of 4-(3-aminothieno-[2,3-b]pyridin-2-yl)coumarins
  作者：S. V. Gorelov、S. P. Bondarenko、M. S. Frasinyuk

  DOI：10.1007/s10593-012-1083-2

  日期：2012.9

  Substituted 4-[(3-cyanopyridin-2-yl)thiomethyl]coumarins have been synthesized by the alkylation of 2-mercapto-4,6-dimethylnicotinonitrile with 4-chloromethylcoumarins. Substituted 4-(3-amino-thieno[2,3-b]pyridin-2-yl)coumarins have been obtained by a subsequent intramolecular condensation of the methylene and cyano groups. 6H-Chromeno[4,3-d]thieno[3,2-b:5,4-b']dipyridin-6-ones were isolated as a result of the interaction of these compounds with aldehydes, and their aminomethyl derivatives were synthesized.
• Synthesis of Coumarin-4-Ylmethyl Phosphonic Acids
  作者：K. M. Kondratyuk、V. A. Dluzhevskii、S. P. Bondarenko、V. S. Brovarets、M. S. Frasinyuk

  DOI：10.1007/s10600-019-02766-9

  日期：2019.7

  New coumarin-4-ylmethylphosphonates and coumarin-4-ylmethylphosphonic acids were synthesized and tested for antiviral activity.

  合成了新的香豆素-4-基甲基膦酸酯和香豆素-4-基甲基膦酸并测试了抗病毒活性。