(1S,2R,5R,6S,7R)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one | 165173-58-0

• 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: (1S,2R,5R,6S,7R)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 165173-58-0
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: NWEUVIWNYFQLSO-IWYOCHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,6S,7R)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 、 methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-oxopropionate 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以29%的产率得到methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(6(R)-methyl-5-oxo-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3(S)-yloxy)acrylate
  参考文献：
  名称：

  Synthesis of a Phthaloylglycine-Derived Strigol Analogue and Its Germination Stimulatory Activity toward Seeds of the Parasitic Weeds Striga hermonthica and Orobanche crenata

  摘要：

  The newly designed strigol analogue Nijmegen 1 (rac 7) was prepared in high overall yield starting from N-phthaloylglycine, This relatively simple analogue exhibits high bioactivity in the stimulation of germination of seeds of the parasitic weeds Striga hermonthica and Orobanche crenata. Nijmegen 1 was resolved in its enantiomers 7 and ent 7 by using the homochiral latent D-rings ent 11 and ent 12. The enantiomers 7 and ent 7 show significant differences in germination activity.

  DOI：

  10.1021/jf9604504
• 作为产物：
  描述：

  5(RS)-hydroxy-2(SR)-methyl-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one 在 吡啶 、 氯化亚砜 作用下， 反应 1.0h， 以66%的产率得到(1S,2R,5R,6S,7R)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
  参考文献：
  名称：

  Asymmetric synthesis of a D-ring synthon for strigol analogues and its application to the synthesis of all four stereoisomers of germination stimulant GR7

  摘要：

  DOI：

  10.1016/0040-4020(95)98701-i

文献信息

• Synthesis of All Eight Stereoisomers of the Germination Stimulant Sorgolactone
  作者：Yukihiro Sugimoto、Suzanne C. M. Wigchert、Jan Willem J. F. Thuring、Binne Zwanenburg

  DOI：10.1021/jo9718408

  日期：1998.2.1

  The naturally occurring sesquiterpene sorgolactone (2) belongs to the class of "strigolactones", which are highly potent germination stimulants for seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all eight stereoisomers of sorgolactone and to evaluate their activities in the stimulation of germination of S. hermontica and O. crenata. Two racemic diastereomers of the ABC part of sorgolactone, rac.10a and rac.10b respectively, were prepared and coupled with homochiral latent D-ring synthons 12 and ent.12. In this manner, four mixtures of two separable (protected) sorgolactone diastereomers were obtained. Deprotection gave all eight target compounds as single isomers. Bioassays revealed that only those isomers possessing the same stereochemistry as natural sorgolactone at two adjacent chiral centers exhibit high biological activities.
• 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.
• Asymmetric Synthesis of All Stereoisomers of the Strigol Analogue GR24. Dependence of Absolute Configuration on Stimulatory Activity of <i>Striga hermonthica</i> and <i>Orobanche crenata</i> Seed Germination
  作者：Jan Willem J. F. Thuring、Gerard H. L. Nefkens、Binne Zwanenburg

  DOI：10.1021/jf960466u

  日期：1997.6.1

  All four optically pure stereoisomers of the strigol analogue GR24 were prepared via two different routes. In the first approach enantiopure ABC-fragments 4 were used as the chiral source, whereas in the alternative route both antipodes of the latent D-ring 6 were employed. Bioassays revealed significant differences in activity between the four stereoisomers in the stimulation of germination of the parasitic weeds Striga hermonthica and Orobanche crenata.