(7S)-9-bromo-7-methyl-1,4-dioxaspiro[4.4]non-8-ene | 1265883-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7S)-9-bromo-7-methyl-1,4-dioxaspiro[4.4]non-8-ene
• CAS: 1265883-41-7
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: XPXPLYLLKMNXHH-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7S)-9-bromo-7-methyl-1,4-dioxaspiro[4.4]non-8-ene 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate
  参考文献：
  名称：

  Total Synthesis of Lathyranoic Acid A

  摘要：

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.

  DOI：

  10.1021/jo102033h
• 作为产物：
  描述：

  (-)-(S)-4-methyl-2-cyclopentenone 在 溴 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.08h， 生成 (7S)-9-bromo-7-methyl-1,4-dioxaspiro[4.4]non-8-ene
  参考文献：
  名称：

  Total Synthesis of Lathyranoic Acid A

  摘要：

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.

  DOI：

  10.1021/jo102033h

文献信息

• Total Synthesis of Lathyranoic Acid A
  作者：Li-Fang Yu、Hai-Ning Hu、Fa-Jun Nan

  DOI：10.1021/jo102033h

  日期：2011.3.4

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.