(3aS,9aS,9bS)-6-Methyl-3,9-dimethylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one | 90807-57-1

• 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: (3aS,9aS,9bS)-6-Methyl-3,9-dimethylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• 英文别名: (3aS,9aS,9bS)-6-methyl-3,9-bis(methylene)-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one；(3aS,9aS,9bS)-6-methyl-3,9-dimethylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• CAS: 90807-57-1
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: BJYLDDWXWJTGPU-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (11S)-1-oxoeudesm-2-eno-12,6α-lactone 在 吡啶 、 双氧水 、 溶剂黄146 、 lithium tri-t-butoxyaluminum hydride 、 汞 、 锌 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 9.5h， 生成 (3aS,9aS,9bS)-6-Methyl-3,9-dimethylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
  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

文献信息

• 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。

表征谱图