(5S)-5-methylhepta-1,6-dien-3-one | 1265883-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S)-5-methylhepta-1,6-dien-3-one
• CAS: 1265883-12-2
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: PTCOBZQQIMLMED-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S)-5-methylhepta-1,6-dien-3-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 溴 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 17.08h， 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
• 作为产物：
  描述：

  (S)-ethyl 3-methyl-4-oxobutanoate 在 异丙基氯化镁 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 (5S)-5-methylhepta-1,6-dien-3-one
  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.