3-isobutoxy-6-(3-methylbut-3-en-1-yl)cyclohex-2-en-1-one | 1237493-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isobutoxy-6-(3-methylbut-3-en-1-yl)cyclohex-2-en-1-one
• CAS: 1237493-60-5
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: YSFPQZIHYYMEQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-chloroallyl chloroformate 、 3-isobutoxy-6-(3-methylbut-3-en-1-yl)cyclohex-2-en-1-one 在 正丁基锂 、 二异丙胺 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.13h， 以61%的产率得到2-chloroallyl (5-isobutoxy-2-(3-methylbut-3-en-1-yl)cyclohexa-1,5-dien-1-yl) carbonate
  参考文献：
  名称：

  A general enantioselective route to the chamigrene natural product family

  摘要：

  Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.128
• 作为产物：
  描述：

  4-碘-2-甲基丁-1-烯 、 3-异丁氧基-2-环己烯酮 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 2.03h， 以30%的产率得到3-isobutoxy-6-(3-methylbut-3-en-1-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  A general enantioselective route to the chamigrene natural product family

  摘要：

  Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.128