3-(piperidine-1-carbonyl)-4H-chromen-4-one | 52817-16-0

• 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: 3-(piperidine-1-carbonyl)-4H-chromen-4-one
• 英文别名: 1-<(4-Oxo-4H-1-benzopyran-3-yl)carbonyl>piperidin；1-(4-oxo-4H-chromene-3-carbonyl)-piperidine；1-[(4-oxo-4H-1-benzopyran-3-yl)carbonyl]piperidine；3-(Piperidine-1-carbonyl)chromen-4-one
• CAS: 52817-16-0
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: YWUXFGWYJDHJNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3-(piperidine-1-carbonyl)-4H-chromen-4-one 、 肌氨酸 在 乙酰氯 作用下， 以 苯 、 异丙醇 、 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到2-methyl-9a-(piperidine-1-carbonyl)-1,2,3,3a-tetrahydrochromeno[2,3-c]pyrrol-9(9aH)-one hydrochloride
  参考文献：
  名称：

  Substituted chromones in [3+2] cycloadditions with nonstabilized azomethine ylides: synthesis of 1-benzopyrano[2,3-c]pyrrolidines and 1-benzopyrano[2,3-c:3,4-c′]dipyrrolidines

  摘要：

  Chromones bearing electron-withdrawing substituents at the 2- or 3-position react with nonstabilized azomethine ylides to produce 1-benzopyrano[2,3-c]pyrrolidines in good yields. Reactions of 3cyanochromones proceed diastereoselectively to give 1-benzopyrano[2,3-c]pyrrolidines and tetrahydro-1H-spiro[chromeno[2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbonitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno[2,3-c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.090
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 sodium chlorite 、 氯化亚砜 、 氨基磺酸 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 3-(piperidine-1-carbonyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of chromone-3-carboxamides

  摘要：

  DOI：

  10.24820/ark.5550190.p011.356

文献信息

• Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids
  申请人：Warner-Lambert Company

  公开号：US03937837A1

  公开（公告）日：1976-02-10

  Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids having the structural formula: ##SPC1## Wherein R.sub.1 represents hydrogen, halogen, lower alkyl, hydroxy, lower alkoxy, or acyloxy; R.sub.2 represents hydrogen, lower alkyl, fluorinated lower alkyl, alkoxycarbonyl, carboxy, or lower alkyl carboxylic acid; Z represents cyano, carboxy, alkoxycarbonyl, or ##EQU1## wherein X represents amino, N-lower-alkylamino, hydroxylamino, N-lower-alkylhydroxylamino, ureido, piperidino, or anilino, with the proviso that when R.sub.2 represents hydrogen, Z represents cyano or ##EQU2## wherein X has the same meaning as given above; and wherein R.sub.2 and Z together may form a substituted pyrrole ring; and the corresponding non-toxic, pharmaceutically acceptable salts.

  替代的咔喃-3-羧腈、羧酰胺和羧酸，具有以下结构式：##SPC1## 其中 R.sub.1 代表氢、卤素、低烷基、羟基、低烷氧基或酰氧基；R.sub.2 代表氢、低烷基、氟代低烷基、烷氧羰基、羧基或低烷基羧酸；Z 代表氰基、羧基、烷氧羰基或##EQU1## 其中 X 代表氨基、N-低烷基氨基、羟基氨基、N-低烷基羟基氨基、脲基、哌啶基或苯胺基，但当 R.sub.2 代表氢时，Z 代表氰基或##EQU2## 其中 X 的含义与上述相同；且其中 R.sub.2 和 Z 可以共同形成取代的吡咯环；以及相应的非毒性、药学上可接受的盐。
• 3-Cyanochromones in [3+2] cycloadditions with an azomethine ylide derived from sarcosine and formaldehyde. A short synthesis of 1-benzopyrano[2,3-c:3,4-c′]dipyrrolidines
  作者：Vyacheslav Ya. Sosnovskikh、Mikhail Yu. Kornev、Vladimir S. Moshkin

  DOI：10.1016/j.tetlet.2013.10.154

  日期：2014.1

  Reactions of 3-cyanochromones with sarcosine and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[2,3-c]pyrrolidines and tetrahydro-1H-spiro[chromeno[2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbonitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno[2,3c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2013 Elsevier Ltd. All rights reserved.
• US3937837A
  申请人：——

  公开号：US3937837A

  公开（公告）日：1976-02-10
• Synthesis and biological evaluation of chromone-3-carboxamides
  作者：Allen T. Gordon、Isaiah D.I. Ramaite、Simon. S. Mnyakeni-Moleele

  DOI：10.24820/ark.5550190.p011.356

  日期：——
• Substituted chromones in [3+2] cycloadditions with nonstabilized azomethine ylides: synthesis of 1-benzopyrano[2,3-c]pyrrolidines and 1-benzopyrano[2,3-c:3,4-c′]dipyrrolidines
  作者：Vyacheslav Y. Sosnovskikh、Mikhail Y. Kornev、Vladimir S. Moshkin、Evgeny M. Buev

  DOI：10.1016/j.tet.2014.09.090

  日期：2014.12

  Chromones bearing electron-withdrawing substituents at the 2- or 3-position react with nonstabilized azomethine ylides to produce 1-benzopyrano[2,3-c]pyrrolidines in good yields. Reactions of 3cyanochromones proceed diastereoselectively to give 1-benzopyrano[2,3-c]pyrrolidines and tetrahydro-1H-spiro[chromeno[2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbonitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno[2,3-c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2014 Elsevier Ltd. All rights reserved.