(11S)-guaia-1(10),3-dieno-12,6α-lactone | 38236-18-9

• 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: (11S)-guaia-1(10),3-dieno-12,6α-lactone
• 英文别名: (3S,3aS,9aS,9bS)-3,6,9-trimethyl-3a,4,5,7,9a,9b-hexahydro-3H-azuleno[4,5-b]furan-2-one
• CAS: 38236-18-9
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: WBHVRMWEPJHOHP-PYJNHQTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (11S)-guaia-1(10),3-dieno-12,6α-lactone 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 tannunolide B 、 6-epi-tannunolide B
  参考文献：
  名称：

  Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

  摘要：

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10392-1
• 作为产物：
  描述：

  3β-tetrahydro-O-acetylisophotosantonic lactone 在 吡啶 、 氢氧化钾 、 三氟甲磺酸酐 、 lithium carbonate 、 lithium bromide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 13.55h， 生成 (11S)-guaia-1(10),3-dieno-12,6α-lactone
  参考文献：
  名称：

  Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

  摘要：

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10392-1

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。
• Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives
  作者：Saori Yuuya、Hisahiro Hagiwara、Toshio Suzuki、Masayoshi Ando、Atsushi Yamada、Kouji Suda、Takao Kataoka、Kazuo Nagai

  DOI：10.1021/np980092u

  日期：1999.1.1

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.
• 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.
• Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides
  作者：Victoria Bargues、Gonzalo Blay、Luz Cardona、Begoña García、JoséR. Pedro

  DOI：10.1016/s0040-4020(97)10392-1

  日期：1998.2

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.