(3aR,7S,8aR)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one | 1256454-18-8

• 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: (3aR,7S,8aR)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
• 英文别名: (3aR,7S,8aR)-6-ethenyl-7-methyl-3-methylidene-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• CAS: 1256454-18-8
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: LWWRXPBUAMTDTK-XXILOJSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (3aR,7S,8aR)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到8-表苍耳亭
  参考文献：
  名称：

  Total synthesis of xanthanolides

  摘要：

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.061
• 作为产物：
  描述：

  (3R,3aS,7S,8aR)-3-bromo-3,7-dimethyl-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以99%的产率得到(3aR,7S,8aR)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
  参考文献：
  名称：

  Total synthesis of xanthanolides

  摘要：

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.061

文献信息

• Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives
  作者：Hiromasa Yokoe、Kentaro Noboru、Yuki Manabe、Masahiro Yoshida、Hirofumi Shibata、Kozo Shishido

  DOI：10.1248/cpb.c12-00519

  日期：——

  An enantioselective synthesis of 8-epi-xanthatin (9) has been accomplished starting from the bicyclic lactone 3, which has been used for the synthesis of other xanthanolides, sundiversifolide (4) and diversifolide (5), through a synthetic route without the use of a selenium species. Additionally we have evaluated antimicrobial activities of five natural xanthanolides and their derivatives. Although

  从双环内酯3开始完成对映体8-表皮-黄嘌呤（9）的对映选择性合成，该双环内酯3已通过不使用的合成路线用于合成其他黄药内酯，多酚（4）和多酚（5）。硒物种。此外，我们还评估了五种天然黄原酸及其衍生物的抗菌活性。尽管合成的黄嘌呤内酯对耐甲氧西林的金黄色葡萄球菌（MRSA）没有任何活性，但某些合成中间体确实表现出中等的抗菌活性。
• Total synthesis of xanthanolides
  作者：Kazumasa Matsuo、Keiko Ohtsuki、Takashi Yoshikawa、Kozo Shishido、Kaori Yokotani-Tomita、Mitsuru Shindo

  DOI：10.1016/j.tet.2010.08.061

  日期：2010.10

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.