4-amino-5-ethyl-2(5H)-furanone | 66316-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-amino-5-ethyl-2(5H)-furanone
• 英文别名: 3-amino-2-ethyl-2H-furan-5-one
• CAS: 66316-87-8
• 化学式: C₆H₉NO₂
• mdl: MFCD12828505
• 分子量: 127.143
• InChiKey: FOTOFVUOURYGNI-UHFFFAOYSA-N

物化性质

• 沸点：
  264.8±29.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-5-ethyl-2(5H)-furanone 以 乙醇 为溶剂， 反应 60.0h， 生成 trans-9-(3-bromo-4-fluorophenyl)-3-ethyl-5,9-dihydro-3H,4H-2-oxa-6-thia-4-azacyclopenta[b]naphthalene-1,8-dione
  参考文献：
  名称：

  Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener

  摘要：

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

  DOI：

  10.1021/jm060549u
• 作为产物：
  描述：

  2-acetoxybutanenitrile 在 bis(acetylacetonate)nickel(II) 、 lithium hexamethyldisilazane 作用下， 以28%的产率得到4-amino-5-ethyl-2(5H)-furanone
  参考文献：
  名称：

  通过酯烯醇化物的分子内和分子间腈加成合成 4-氨基-2(5H)-呋喃酮。一种抗肿瘤抗生素担子的碳框架构建

  摘要：

  公开了 4-氨基-2(5H)-呋喃酮的两条新路线。一种是基于乙酸叔丁酯或丙酸叔丁酯的烯醇镁与 O-保护的氰醇的反应，然后进行酸处理，在单一操作中实现酯基的水解、脱保护、烯烃异构化和内酯化。另一种是α-酰氧基腈的碱诱导环合。这两种方法均应用于构建抗肿瘤抗生素basidalin的碳骨架。

  DOI：

  10.1246/bcsj.60.2139

文献信息

• New synthetic methods for 4-amino-2(5H)-furanones
  作者：Tamejiro Hiyama、Haruhito Oishi、Hiroyuki Saimoto

  DOI：10.1016/s0040-4039(00)94853-6

  日期：1985.1
• HIYAMA, TAMEJIRO;OISHI, HARUHITO;SAIMOTO, HIROYUKI, TETRAHEDRON LETT., 1985, 26, N 20, 2459-2462
  作者：HIYAMA, TAMEJIRO、OISHI, HARUHITO、SAIMOTO, HIROYUKI

  DOI：——

  日期：——
• XIYAMA, TAMEHDZIRO;OISI, XARUXITO
  作者：XIYAMA, TAMEHDZIRO、OISI, XARUXITO

  DOI：——

  日期：——
• Synthesis of 4-Amino-2(5<i>H</i>)-furanones through Intra- and Intermolecular Nitrile Addition of Ester Enolates. Construction of Carbon Framework of an Antitumor Antibiotic Basidalin
  作者：Tamejiro Hiyama、Haruhito Oishi、Yukari (nee Kusano) Suetsugu、Kiyoharu Nishide、Hiroyuki Saimoto

  DOI：10.1246/bcsj.60.2139

  日期：1987.6

  ester group, deprotection, olefin isomerization and lactonization all in a single operation. The other is base-induced ringclosure of α-acyloxy nitriles. The two methods are applied to construction of the carbon framework of an antitumor antibiotic basidalin.

  公开了 4-氨基-2(5H)-呋喃酮的两条新路线。一种是基于乙酸叔丁酯或丙酸叔丁酯的烯醇镁与 O-保护的氰醇的反应，然后进行酸处理，在单一操作中实现酯基的水解、脱保护、烯烃异构化和内酯化。另一种是α-酰氧基腈的碱诱导环合。这两种方法均应用于构建抗肿瘤抗生素basidalin的碳骨架。
• Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3<i>H</i>,4<i>H</i>-2,6-dioxa-4- azacyclopenta[<i>b</i>]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener
  作者：Robert J. Altenbach、Michael E. Brune、Steven A. Buckner、Michael J. Coghlan、Anthony V. Daza、Adebola Fabiyi、Murali Gopalakrishnan、Rodger F. Henry、Albert Khilevich、Michael E. Kort、Ivan Milicic、Victoria E. Scott、Jamie C. Smith、Kristi L. Whiteaker、William A. Carroll

  DOI：10.1021/jm060549u

  日期：2006.11.1

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.