4-hydroxy-6-(2',4'-dioxo-pentyl)-pyrone | 83095-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-6-(2',4'-dioxo-pentyl)-pyrone
• 英文别名: 1-(4-Hydroxy-6-oxopyran-2-yl)pentane-2,4-dione；1-(4-hydroxy-6-oxopyran-2-yl)pentane-2,4-dione
• CAS: 83095-25-4
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: ASEYYXCDIJFBOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,6-dimethoxy-2-pyrone 在 碘代三甲硅烷 、 lithium diisopropyl amide 作用下， 以 氯仿 为溶剂， 反应 52.17h， 生成 4-hydroxy-6-(2',4'-dioxo-pentyl)-pyrone
  参考文献：
  名称：

  通过4,6-二甲氧基-2-吡喃酮与单和二酮阴离子的缩合反应制备3,5,7-三酮和3,5,7,9-四酮酸的烯醇内酯

  摘要：

  丙酮，苯乙酮，乙酰丙酮和苯甲酰丙酮的阴离子与4,6-二甲氧基-2-吡喃酮的缩合得到相应的6个取代的4-甲氧基-2-吡喃酮的良好收率，将其通过碘代三甲基硅烷脱甲基转化为4-羟基类似物。 。

  DOI：

  10.1016/s0040-4039(00)87236-6

文献信息

• Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum
  作者：Aphacha Jindaprasert、Karin Springob、Jürgen Schmidt、Wanchai De-Eknamkul、Toni M. Kutchan

  DOI：10.1016/j.phytochem.2008.03.013

  日期：2008.12

  To isolate cDNAs involved in the biosynthesis of acetate-derived naphthoquinones in Drosophyllum lusitanicum, an expressed sequence tag analysis was performed. RNA from callus cultures was used to create a cDNA library from which 2004 expressed sequence tags were generated. One cDNA with similarity to known type III polyketicle synthases was isolated as full-length sequence and termed DluHKS. The translated polypepticle sequence of DIuHKS showed 51-67% identity with other plant type III PKSs. Recombinant DIuHKS expressed in Escherichia coli accepted acetyl-coenzyme A (CoA) as starter and carried out sequential decarboxylative condensations with malonyl-CoA yielding ot-pyrones from three to six acetate units. However, naphthalenes, the expected products, were not isolated. Since the main compound produced by DIuHKS is a hexaketicle ot-pyrone, and the naphthoquinones in D. lusitanicum are composed of six acetate units, we propose that the enzyme provides the backbone of these secondary metabolites. An involvement of accessory proteins in this biosynthetic pathway is discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• RAY, J. A.;HARRIS, T. M., TETRAHEDRON LETT., 1982, 23, N 19, 1971-1974
  作者：RAY, J. A.、HARRIS, T. M.

  DOI：——

  日期：——
• Preparation of enol lactones of 3,5,7-triketo and 3,5,7,9-tetraketo acids by the condensation of 4,6-dimethoxy-2-pyrone with anions of mono- and diketones
  作者：John A. Ray、Thomas M. Harris

  DOI：10.1016/s0040-4039(00)87236-6

  日期：1982.1

  Condensation of the anions of acetone, acetophenone, acetylacetone and benzoylacetone with 4,6-dimethoxy-2-pyrone afforded good yields of the corresponding 6 substituted 4-methoxy-2-pyrones which were converted to the 4-hydroxy analogs by demethylation with iodotrimethylsilane.

  丙酮，苯乙酮，乙酰丙酮和苯甲酰丙酮的阴离子与4,6-二甲氧基-2-吡喃酮的缩合得到相应的6个取代的4-甲氧基-2-吡喃酮的良好收率，将其通过碘代三甲基硅烷脱甲基转化为4-羟基类似物。 。