(3aS,8S,8bR,2'S)-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

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3aS,8S,8bR,2'S)-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
• 英文别名: 8-episorgolactone；(3E,3aS,8S,8bR)-8-methyl-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,5,6,7,8,8b-hexahydro-3aH-indeno[1,2-b]furan-2-one
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: KHSREFIWULNDAB-CEQJQLPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-(-)-香茅酸 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 pyridinium hydrobromide perbromide 、 过碘酸 、 间氯过氧苯甲酸 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 溶剂黄146 、 二甲基亚砜 、 丙酮 、 苯 为溶剂， 反应 117.5h， 生成 (3aS,8S,8bR,2'S)-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：

  (±)- 和 (+)-Sorgolactone 的合成，来自双色高粱的萌发刺激剂

  摘要：

  (±)-2a 是山梨内酯结构的外消旋体及其三种外消旋立体异构体的合成，中间体 (±)-10 和最终产物 (±)-2a 的立体结构已通过 X- 确认射线分析。其旋光形式 (3aR,8S,8bS,2'R)-(+)-2a 也由 (S)-(-)-香茅醛通过采用 18 至 19 的自由基环化作为关键步骤制备。将合成产品的光谱特性与天然山梨内酯的光谱特性进行比较。使用三叶草 (Orobanche minor) 种子的生物测定表明，所有立体异构体都强烈刺激它们的发芽。

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2183::aid-ejoc2183>3.0.co;2-4

文献信息

• Synthesis of (3aR,8S,8bS,2′R)-(+)-sorgolactone and its stereoisomers, the germination stimulant from sorghum bicolor
  作者：Kenji Mori、Junichi Matsui

  DOI：10.1016/s0040-4039(97)10078-8

  日期：1997.11

  Methyl (S)-citronellate (2) was converted to (3aR,8S,8bS,2′R)-(+)-sorgolactone (1a) by employing the radical cyclization of 6 to 7 as the key-step. Three other stereoisomers (1b, 1c and 1d) of sorgolactone were also prepared. The CD spectrum of 1a was in accord with that reported for the natural product.

  甲基（小号）-citronellate（2）转化为（3A - [R，8小号，8B小号，2' - [R sorgolactone（ - ） - （+）1A通过采用的自由基环化）6至7的关键步骤。还制备了高粱内酯的其他三种立体异构体（1b，1c和1d）。1a的CD光谱与天然产物的CD光谱一致。
• Synthesis and Biological Evaluation of the Four Racemic Stereoisomers of the Structure Proposed for Sorgolactone, the Germination Stimulant from Sorghum bicolor
  作者：Kenji Mori*、Junichi Matsui、Masahiko Bando、Masaru Kido、Yasutomo Takeuchi

  DOI：10.1016/s0040-4039(97)00379-1

  日期：1997.4

  The synthesis of the racemates of the structure 1 proposed for sorgolactone and its three stereoisomers was achieved by confirming the stereostructures of the intermediate (±)-6 and the final product (±)-1 by X-ray analyses. Biological evaluation of the products employing clover broomrape (Orobanche minor) seeds revealed that the order of activity as a germination stimulant was (±)-strigol ≈ (±)-9

  提出用于高粱内酯及其三种立体异构体的结构1的外消旋体的合成，是通过X射线分析确定中间体（±）-6和最终产物（±）-1的立体结构而实现的。采用三叶草肉苁蓉产品的生物评价（列当次要）种子表明活性的作为发芽兴奋剂顺序为（±）-strigol≈（±） - 9 ≥（±） - 12 >（±） - 1 >（± ）-11。©1997爱思唯尔科学有限公司。
• 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.
• Syntheses of (±)- and (+)-Sorgolactone, the Germination Stimulant fromSorghum bicolor
  作者：Junichi Matsui、Masahiko Bando、Masaru Kido、Yasutomo Takeuchi、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2183::aid-ejoc2183>3.0.co;2-4

  日期：1999.9

  Syntheses of (±)-2a, the racemate of the structure proposed for sorgolactone, and its three racemic stereoisomers have been accomplished with confirmation of the stereostructures of the intermediate (±)-10 and the final product (±)-2a by X-ray analysis. Its optically active form, (3aR,8S,8bS,2′R)-(+)-2a, has also been prepared from (S)-(–)-citronellal by employing radical cyclization of 18 to 19 as

  (±)-2a 是山梨内酯结构的外消旋体及其三种外消旋立体异构体的合成，中间体 (±)-10 和最终产物 (±)-2a 的立体结构已通过 X- 确认射线分析。其旋光形式 (3aR,8S,8bS,2'R)-(+)-2a 也由 (S)-(-)-香茅醛通过采用 18 至 19 的自由基环化作为关键步骤制备。将合成产品的光谱特性与天然山梨内酯的光谱特性进行比较。使用三叶草 (Orobanche minor) 种子的生物测定表明，所有立体异构体都强烈刺激它们的发芽。