threo-6-(1',2'-dihydroxypentyl)-2H-pyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: threo-6-(1',2'-dihydroxypentyl)-2H-pyran-2-one
• 英文别名: 6-[(1R,2S)-1,2-dihydroxypentyl]pyran-2-one
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: VPAQOCIIZZGSDX-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  threo-6-(1',2'-dihydroxypentyl)-2H-pyran-2-one 、 (S)-(+)-alpha-甲氧基苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1S,2R)-1-(2-oxo-2H-pyran-6-yl)pentane-1,2-diyl (2S,2'S)-bis(2-methoxy-2-phenylacetate) 、 (1R,2S)-1-(2-oxo-2H-pyran-6-yl)pentane-1,2-diyl (2S,2'S)-bis(2-methoxy-2-phenylacetate)
  参考文献：
  名称：

  Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp.

  摘要：

  A comparative study of the secondary metabolism of two Trichoderma spp. with that of the Thctf1 transcription factor gene null mutant of Trichoderma harzianum 34 was carried out in order to deepen our knowledge of the biosynthetic pathway and mode of action of 6-pentyl-2H-pyran-2-one (1) and its derivatives as biocontrol agents. New isolated metabolites have shed light on the detoxification mechanism of 6-pentyl-pyranone by Trichoderma spp. All new compounds were synthesized and their stereoisomer characterized. The absolute configuration of 6-[(1'R,2'S)-dihydroxypentyl]-2H-pyran-2-one and 6-((1'S,2'R)-2'-propyloxiran-1-yl)-2H-pyran-2-one was determined by NMR analysis of the corresponding Mosher's esters. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.051
• 作为产物：
  描述：

  6-(pent-1'-enyl)-2H-pyran-2-one 在 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以80%的产率得到threo-6-(1',2'-dihydroxypentyl)-2H-pyran-2-one
  参考文献：
  名称：

  Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp.

  摘要：

  A comparative study of the secondary metabolism of two Trichoderma spp. with that of the Thctf1 transcription factor gene null mutant of Trichoderma harzianum 34 was carried out in order to deepen our knowledge of the biosynthetic pathway and mode of action of 6-pentyl-2H-pyran-2-one (1) and its derivatives as biocontrol agents. New isolated metabolites have shed light on the detoxification mechanism of 6-pentyl-pyranone by Trichoderma spp. All new compounds were synthesized and their stereoisomer characterized. The absolute configuration of 6-[(1'R,2'S)-dihydroxypentyl]-2H-pyran-2-one and 6-((1'S,2'R)-2'-propyloxiran-1-yl)-2H-pyran-2-one was determined by NMR analysis of the corresponding Mosher's esters. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.051

文献信息

• Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp.
  作者：Mourad Daoubi、Cristina Pinedo-Rivilla、M. Belén Rubio、Rosa Hermosa、Enrique Monte、Josefina Aleu、Isidro G. Collado

  DOI：10.1016/j.tet.2009.04.051

  日期：2009.6

  A comparative study of the secondary metabolism of two Trichoderma spp. with that of the Thctf1 transcription factor gene null mutant of Trichoderma harzianum 34 was carried out in order to deepen our knowledge of the biosynthetic pathway and mode of action of 6-pentyl-2H-pyran-2-one (1) and its derivatives as biocontrol agents. New isolated metabolites have shed light on the detoxification mechanism of 6-pentyl-pyranone by Trichoderma spp. All new compounds were synthesized and their stereoisomer characterized. The absolute configuration of 6-[(1'R,2'S)-dihydroxypentyl]-2H-pyran-2-one and 6-((1'S,2'R)-2'-propyloxiran-1-yl)-2H-pyran-2-one was determined by NMR analysis of the corresponding Mosher's esters. (C) 2009 Elsevier Ltd. All rights reserved.