1-oxoeudesma-2,4-dien-11βH-12,6α-olide | 88010-70-2

• 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-oxoeudesma-2,4-dien-11βH-12,6α-olide
• 英文别名: (3S,3aS,5aR,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,6-dione
• CAS: 88010-70-2
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: CHUWSGRBMLBSSX-MJVIGCOGSA-N

物化性质

• 沸点：
  427.6±34.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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-oxoeudesma-2,4-dien-11βH-12,6α-olide 在 氧气 、 亚甲兰 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 26.67h， 生成 1-Oxo-2α,3α;4α,5α-diepoxyeudesman-11βH-12,6α-olide
  参考文献：
  名称：

  New oxygenated eudesmanolides from artemisia herba-alba

  摘要：

  DOI：

  10.1016/s0040-4020(01)90092-4
• 作为产物：
  描述：

  11,13-dihydroridentin 在 chromium(VI) oxide 、 硫酸 作用下， 以 溶剂黄146 、 乙醇 为溶剂， 反应 2.33h， 以60 mg的产率得到1-oxoeudesma-2,4-dien-11βH-12,6α-olide
  参考文献：
  名称：

  Structure of the sesquiterpene lactone artapshinin

  摘要：

  DOI：

  10.1007/bf02249633

文献信息

• A Short-Step Synthesis of Sesquiterpene Lactone, 1-Oxoeudesma-2,4-dien-11βH-12, 6α-Olide, Isolated from Artemisia Herba-Alba and its Derivatives
  作者：T. Kawamata、K. Nagashima、R. Nakai、T. Tsuji

  DOI：10.1080/00397919608003873

  日期：1996.1

  Abstract 1-Oxoeudesma-2,4-dien-11 βH-12,6α-olide(1) isolated from the genus Artemisia herb-alba was synthesized from α-santonin in a two-step sequence. The key step is the 1,3 oxidative rearrangement of dienol 7.

  摘要 1-Oxoeudesma-2,4-dien-11 βH-12,6α-olide(1) 是从青蒿属中分离出来的，由α-santonin 分两步合成。关键步骤是二烯醇 7 的 1,3 氧化重排。
• Structure of maritimin, a sesquiterpene lactone from artemisia maritima gallica
  作者：Antonio G. González、Antonio Gallindo、Horacio Mansilla、Angeles Gutiérrez

  DOI：10.1016/s0031-9422(00)82667-9

  日期：1981.1

  Abstract 1-Keto-6β,7α,11β-H-selin-4(5)-en-6,12-olide, vulgarin and a new eudesmanolide, maritimin, were isolated from Artemisia maritima gallica . The structure and stereochemistry of this lactone have been determined by spectral studies and chemical transformations.

  摘要 从 Artemisia maritima Gallica 中分离得到 1-Keto-6β,7α,11β-H-selin-4(5)-en-6,12-olide, vulgarin 和一种新的eudesmanolide, maritimin。该内酯的结构和立体化学已通过光谱研究和化学转化确定。
• 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。
• 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.
• 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