(+)-3α,4α-epoxy-5,7αH,6,11βH-guai-(1,10)-en-6,12-olide | 124097-47-8

• 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: (+)-3α,4α-epoxy-5,7αH,6,11βH-guai-(1,10)-en-6,12-olide
• 英文别名: (11S)-3α,4α-epoxyguai-1(10)-eno-12,6α-lactone；(+)-11βH,13-dihydroludartin；11βH,13-dihydroludartin；(+)-11betaH,13-Dihydroludartin；(1S,2S,5S,6S,12R,14S)-5,9,14-trimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
• CAS: 124097-47-8
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: WLJBKCYEKTZMBW-NMZOAQAJSA-N

物化性质

• 沸点：
  394.0±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-3α,4α-epoxy-5,7αH,6,11βH-guai-(1,10)-en-6,12-olide 在 sodium tetrahydroborate 、 W-2 Raney Ni 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 4α-hydroxy-5α,6β,7α,11β-H-guaian-1(10)-en-6,12-olide
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-11βH,13-Dihydroestafiatin, (+)-11βH,13-Dihydroludartin, (−)-Compressanolide, and (−)-11βH,13-Dihydromicheliolide from Santonin

  摘要：

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.

  DOI：

  10.1021/np020109f
• 作为产物：
  描述：

  (-)-3α,4α-epoxy-10α-hydroxy-1,5,7αH,6,11βH-guaian-6,12-olide 在 吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到(+)-3α,4α-epoxy-5,7αH,6,11βH-guai-(1,10)-en-6,12-olide
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-11βH,13-Dihydroestafiatin, (+)-11βH,13-Dihydroludartin, (−)-Compressanolide, and (−)-11βH,13-Dihydromicheliolide from Santonin

  摘要：

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.

  DOI：

  10.1021/np020109f

文献信息

• 10-Epideoxycumambrin b and other constituents of Stevia yaconensis var. subeglandulosa
  作者：Virginia E. Sosa、Juan C. Oberti、Roberto R. Gil、Edmundo A. Rúveda、Virgil L. Goedken、Alicia B、Gutiérrez、Werner Herz

  DOI：10.1016/s0031-9422(00)97888-9

  日期：1989.1

  Stevia yaconensis var. subeglandulosa afforded in addition to the known guaianolides ludartin and dehydroleucodin a new guaianolide 10-epi-8-deoxycumambrin B whose relative and absolute configurations were established by X-ray crystallography. Chemical transformations of ludartin established its relative and absolute stereochemistry.

  摘要 Stevia yaconensis var. 的地上部分。除了已知的愈创木酚内酯 ludartin 和脱氢亮氨酸之外，subeglandulosa 还提供了一种新的愈创木酚内酯 10-epi-8-deoxycumambrin B，其相对和绝对构型由 X 射线晶体学确定。ludartin 的化学转化建立了其相对和绝对立体化学。
• Studies on the syntheses of sesquiterpene lactones. 15. Syntheses of four possible diastereoisomers of Bohlmann's structure of isoepoxyestafiatin. The stereochemical assignment of isoepoxyestafiatin
  作者：Masayoshi Ando、Hideki Yoshimura

  DOI：10.1021/jo00067a056

  日期：1993.7

  The stereochemistry of isoepoxyestafiatin was determined to be 1beta,10beta:3alpha,4alpha-diepoxyguaia-11(13)-eno-12,6alpha-lactone by the syntheses of the four possible diastereoisomers 23-26.
• SOSA, VIRGINIA E.;OBERTI, JUAN C.;GIL, ROBERTO R.;RUVEDA, EDMUNDO A.;GOED+, PHYTOCHEMISTRY, 28,(1989) N, C. 1925-1929
  作者：SOSA, VIRGINIA E.、OBERTI, JUAN C.、GIL, ROBERTO R.、RUVEDA, EDMUNDO A.、GOED+

  DOI：——

  日期：——
• Stereoselective Synthesis of (+)-11<b>β</b><i>H</i>,13-Dihydroestafiatin, (+)-11<b>β</b><i>H</i>,13-Dihydroludartin, (−)-Compressanolide, and (−)-11<b>β</b><i>H</i>,13-Dihydromicheliolide from Santonin
  作者：Victoria Bargues、Gonzalo Blay、Luz Cardona、Begoña García、José R. Pedro

  DOI：10.1021/np020109f

  日期：2002.11.1

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.