4-(chloromethyl)-7,8-dihydrocyclopenta[g]chromen-2(6H)-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: 4-(chloromethyl)-7,8-dihydrocyclopenta[g]chromen-2(6H)-one
• 英文别名: 4-(chloromethyl)-7,8-dihydro-6H-cyclopenta[g]chromen-2-one
• 化学式: C₁₃H₁₁ClO₂
• mdl: MFCD03982029
• 分子量: 234.682
• InChiKey: CLYZMBMCOYONIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 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：

  4-(chloromethyl)-7,8-dihydrocyclopenta[g]chromen-2(6H)-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)-7,8-dihydrocyclopenta[g]chromen-2(6H)-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

文献信息

• One-pot synthesis of 4-heteroaryl-1,2-dihydro-3-benzazepines from 3,4-dihydroisoquinolinium salts or pseudo bases
  作者：Alexander A. Zubenko、Viktor G. Kartsev、Anatolii S. Morkovnik、Ludmila N. Divaeva、Danil V. Alexeenko、Kyrill Yu. Suponitsky、Gennadii S. Borodkin、Alexander I. Klimenko

  DOI：10.1016/j.tetlet.2017.02.036

  日期：2017.3

  novel one-pot synthetic route to the poorly studied 4-heteroaryl-1,2-dihydro-3-benzazepine motif from 3,4-dihydroisoquinolinium compounds is described. The synthetic approach is based on heterocyclic ring expansion of isoquinoline substrates upon reaction with chloromethyl-substituted heterocycles. The scope and limitations of the reaction were investigated to give a series of novel heteroaryl-3-benzazepines

  描述了一种新颖的一锅合成路线，该路线可从3,4-二氢异喹啉鎓化合物转变为研究较少的4-杂芳基-1,2-二氢-3-苯并ze庚因基序。合成方法基于异喹啉底物与氯甲基取代的杂环反应后的杂环扩环。研究了反应的范围和限制，得到了一系列新型的杂芳基-3-苯并b庚因。
• Synthesis and properties of 4-(3-amino-2-benzofuranyl)-coumarins
  作者：M. S. Frasinyuk、S. V. Gorelov、S. P. Bondarenko、V. P. Khilya

  DOI：10.1007/s10593-010-0417-1

  日期：2009.10

  The alkylation of o-cyanophenol by 4-chloromethylcoumarins and subsequent intramolecular condensation by the cyano and methylene groups gives substituted 4-(3-amino-2-benzo-furanyl)coumarins. We studied the reactions of these compounds with acylating agents as well as with aldehydes, which lead to the 6H-[1]benzofuro[3,2-b]chromeno[4,3-d]pyridin-6-one system as the result of consecutive transformations

  4-氯甲基香豆素将邻氰基苯酚烷基化，然后氰基和亚甲基进行分子内缩合，得到取代的4-（3-氨基-2-苯并呋喃基）香豆素。我们研究了这些化合物与酰化剂以及与醛的反应，结果导致生成6H- [1]苯并呋喃[3,2-b] chromeno [4,3-d]吡啶-6-一系统连续变换。
• 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。