(1R,2S,5S,6R,7S)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one | 165069-05-6

• 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: (1R,2S,5S,6R,7S)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 165069-05-6
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: NWEUVIWNYFQLSO-UTABRTIASA-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：

  (1R,2S,5S,6R,7S)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 在 potassium tert-butylate 作用下， 以 邻二氯苯 为溶剂， 生成 (3aR,8S,8bS,2'R)-3-[(E)-2',5'-dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-8-methyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one
  参考文献：
  名称：

  天然发芽兴奋剂高粱内酯的第一个全合成

  摘要：

  报道了高粱内酯的第一个全合成，证实了自然萌发刺激物的拟议结构。

  DOI：

  10.1016/s0040-4039(97)00304-3
• 作为产物：
  描述：

  甲基NA酸酐 在 吡啶 、 氯化亚砜 、 水 、 对甲苯磺酸 、 lithium tri-t-butoxyaluminum hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 42.5h， 生成 (1R,2S,5S,6R,7S)-5-chloro-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
  参考文献：
  名称：

  [EN] COMPOSITION AND METHOD FOR INFLUENCING ENERGY METABOLISM AND TREATING METABOLIC AND OTHER DISORDERS
  [FR] COMPOSITION ET PROCÉDÉ POUR INFLUENCER LE MÉTABOLISME ÉNERGÉTIQUE ET TRAITER DES TROUBLES MÉTABOLIQUES ET D'AUTRES TROUBLES

  摘要：

  提供了一种影响能量代谢和治疗代谢和其他疾病的组合物和方法。一种选择性激活SIRT1的萜类内酯酮通常以一种萜类二内酯的形式存在，具有5-烯氧基呋喃-2-酮基团，如赤露内酯、GR 24或另一种赤露内酯类似物，并且用作影响能量代谢和治疗代谢和其他疾病的治疗剂的方法中。萜类内酯酮可以作为单独的药剂给药，也可以与第二化合物（如黄酮类、香豆素类、单宁或烟酰胺抑制拮抗剂）结合给药。

  公开号：

  WO2012056113A1

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 a D-ring synthon for strigol analogues and its application to the synthesis of all four stereoisomers of germination stimulant GR7
  作者：Jan Willem J.F. Thuring、Gerard H.L. Nefkens、Robert Schaafstra、Binne Zwanenburg

  DOI：10.1016/0040-4020(95)98701-i

  日期：1995.4
• Synthesis of a Phthaloylglycine-Derived Strigol Analogue and Its Germination Stimulatory Activity toward Seeds of the Parasitic Weeds <i>Striga </i><i>hermonthica</i> and <i>Orobanche crenata</i>
  作者：Gérard H. L. Nefkens、Jan Willem J. F. Thuring、Marco F. M. Beenakkers、Binne Zwanenburg

  DOI：10.1021/jf9604504

  日期：1997.6.1

  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.
• 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.