3-(6(S)-methyl-5-oxo-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3(R)-yloxymethylene)-3,3a(R),4,5,6,7,8,8b(S)-octahydroindeno[1,2-b]furan-2-one | 185222-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(6(S)-methyl-5-oxo-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3(R)-yloxymethylene)-3,3a(R),4,5,6,7,8,8b(S)-octahydroindeno[1,2-b]furan-2-one
• 英文别名: (3E,3aR,8bS)-3-[[(1S,2R,3R,6S,7R)-6-methyl-5-oxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-yl]oxymethylidene]-4,5,6,7,8,8b-hexahydro-3aH-indeno[1,2-b]furan-2-one
• CAS: 185222-69-9
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: GGBQAPWCPAWIPK-DEIUJRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(6(S)-methyl-5-oxo-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3(R)-yloxymethylene)-3,3a(R),4,5,6,7,8,8b(S)-octahydroindeno[1,2-b]furan-2-one 以 邻二氯苯 为溶剂， 反应 6.0h， 以30%的产率得到3-(4-methyl-5-oxo-2,5-dihydrofuran-2(R)-yloxymethylene)-3,3a(R),4,5,6,7,8,8b(S)-octahydroindeno[1,2-b]furan-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of All Stereoisomers of Demethylsorgolactone. Dependence of the Stimulatory Activity of Striga hermonthica and Orobanche crenata Seed Germination on the Absolute Configuration

  摘要：

  Strigol and sorgolactone belong to the class of ''strigolactones'', which are highly potent germination stimulants of seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all four stereoisomers of demethylsorgolactone (6), which lacks the methyl group in the A-ring of naturally occurring sorgolactone, and to evaluate their activities in the stimulation of germination of Striga hermonthica and Orobanche crenata seeds. Two diastereomers of demethylsorgolactone (6) were prepared and resolved in the corresponding enantiomers. Bioassays revealed that the germination stimulatory activity Of ii is comparable to that of strigol and that there exist significant differences in activity among the individual stereoisomers.

  DOI：

  10.1021/jf9605106
• 作为产物：
  描述：

  2,3,4,5,6,7-六氢-1H-茚-1-酮 在 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 10.33h， 生成 3-(6(S)-methyl-5-oxo-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3(R)-yloxymethylene)-3,3a(R),4,5,6,7,8,8b(S)-octahydroindeno[1,2-b]furan-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of All Stereoisomers of Demethylsorgolactone. Dependence of the Stimulatory Activity of Striga hermonthica and Orobanche crenata Seed Germination on the Absolute Configuration

  摘要：

  Strigol and sorgolactone belong to the class of ''strigolactones'', which are highly potent germination stimulants of seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all four stereoisomers of demethylsorgolactone (6), which lacks the methyl group in the A-ring of naturally occurring sorgolactone, and to evaluate their activities in the stimulation of germination of Striga hermonthica and Orobanche crenata seeds. Two diastereomers of demethylsorgolactone (6) were prepared and resolved in the corresponding enantiomers. Bioassays revealed that the germination stimulatory activity Of ii is comparable to that of strigol and that there exist significant differences in activity among the individual stereoisomers.

  DOI：

  10.1021/jf9605106

文献信息

• Asymmetric Synthesis of All Stereoisomers of Demethylsorgolactone. Dependence of the Stimulatory Activity of <i>Striga hermonthica</i> and <i>Orobanche crenata</i> Seed Germination on the Absolute Configuration
  作者：Jan Willem J. F. Thuring、Nicole W. J. T. Heinsman、Robèrt W. A. W. M. Jacobs、Gérard H. L. Nefkens、Binne Zwanenburg

  DOI：10.1021/jf9605106

  日期：1997.2.1

  Strigol and sorgolactone belong to the class of ''strigolactones'', which are highly potent germination stimulants of seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all four stereoisomers of demethylsorgolactone (6), which lacks the methyl group in the A-ring of naturally occurring sorgolactone, and to evaluate their activities in the stimulation of germination of Striga hermonthica and Orobanche crenata seeds. Two diastereomers of demethylsorgolactone (6) were prepared and resolved in the corresponding enantiomers. Bioassays revealed that the germination stimulatory activity Of ii is comparable to that of strigol and that there exist significant differences in activity among the individual stereoisomers.