1-oxo-eudesm-2,4(15)-dien-5α,6β,7α,11βH-12,6-olide | 60134-10-3

• 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: 1-oxo-eudesm-2,4(15)-dien-5α,6β,7α,11βH-12,6-olide
• 英文别名: Anhydrovulgarin；(3S,3aS,5aR,9aS,9bS)-3,5a-dimethyl-9-methylidene-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
• CAS: 60134-10-3
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: POALEKYBFVPYJR-KKQCIPQASA-N

物化性质

• 沸点：
  419.8±44.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxo-eudesm-2,4(15)-dien-5α,6β,7α,11βH-12,6-olide 在 吡啶 、 potassium acetate 、 lithium tri-t-butoxyaluminum hydride 、 间氯过氧苯甲酸 、 汞 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 31.5h， 生成 mokkolactone
  参考文献：
  名称：

  Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives

  摘要：

  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.

  DOI：

  10.1021/np980092u
• 作为产物：
  描述：

  (11S)-1,1-(ethylenedioxy)eudesm-3-eno-13,6α-lactone 在 溴 作用下， 以 氯仿 为溶剂， 以63%的产率得到1-oxo-eudesm-2,4(15)-dien-5α,6β,7α,11βH-12,6-olide
  参考文献：
  名称：

  TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN

  摘要：

  以1-oxoeudesm-2-eno-13,6α-内酯为原料，经过7步合成了一系列在A环上具有共同结构单元的愈创木酚内酯，如木香内酯、脱氢木香内酯和eremanthin。关键步骤涉及 1β-mesyloxyeudesm-4(14)-eno-13,6α-内酯的溶剂分解重排。

  DOI：

  10.1246/cl.1984.493

文献信息

• Eudesmanolides from artemisia canariensis
  作者：A.G. González、J. Bermejo、T. Zaragoza

  DOI：10.1016/s0031-9422(00)84050-9

  日期：1983.1
• 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.
• TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN
  作者：Masayoshi Ando、Akio ONO、Kahei Takase

  DOI：10.1246/cl.1984.493

  日期：1984.4.5

  A series of guaianolides such as mokko lactone, dehydrocostus lactone, and eremanthin which posses a common structural unit in A ring have been synthesized from 1-oxoeudesm-2-eno-13,6α-lactone in 7 steps. The key step involves solvolytic rearrangement of 1β-mesyloxyeudesm-4(14)-eno-13,6α-lactone.

  以1-oxoeudesm-2-eno-13,6α-内酯为原料，经过7步合成了一系列在A环上具有共同结构单元的愈创木酚内酯，如木香内酯、脱氢木香内酯和eremanthin。关键步骤涉及 1β-mesyloxyeudesm-4(14)-eno-13,6α-内酯的溶剂分解重排。