(3S,3aS,7S,8aR)-3-bromo-3,7-dimethyl-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one | 1256454-17-7

• 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: (3S,3aS,7S,8aR)-3-bromo-3,7-dimethyl-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
• 英文别名: (3S,3aS,7S,8aR)-3-bromo-6-ethenyl-3,7-dimethyl-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• CAS: 1256454-17-7
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: HRVAXJGIFWRNFK-MGAJZRQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (3S,3aS,7S,8aR)-3-bromo-3,7-dimethyl-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 在 lithium diisopropyl amide 、 四溴化碳 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以43%的产率得到(3R,3aS,7S,8aR)-3-bromo-3,7-dimethyl-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
• 作为产物：
  描述：

  (3S,3aR,7S,8aR)-3,7-dimethyl-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 在 lithium diisopropyl amide 、 四溴化碳 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以39%的产率得到(3R,3aS,7S,8aR)-3-bromo-3,7-dimethyl-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

• 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.