methyl 6-(2-hydroxy-5-oxocyclopent-3-enyl)hexanoate | 132971-11-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-(2-hydroxy-5-oxocyclopent-3-enyl)hexanoate
• 英文别名: Methyl 6-(2-hydroxy-5-oxocyclopent-3-en-1-yl)hexanoate
• CAS: 132971-11-0
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: VZOCYOJJSMZJMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-(2-hydroxy-5-oxocyclopent-3-enyl)hexanoate 在 三氯乙醛 、 三乙胺 、 lithium bromide 、 水 作用下， 以 甲苯 、 正庚烷 为溶剂， 反应 8.5h， 以8 g的产率得到methyl 6-(3-hydroxy-5-oxocyclopent-1-enyl)hexanoate
  参考文献：
  名称：

  Synthesis of 2-Normisoprostol, Methyl 6-(3-Hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)hexanoate

  摘要：

  Synthesis of 2-normisoprostol, methyl 6-(3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)hexanoate (3), employing two-component coupling strategy based on 1,4-addition followed by DDQ-mediated triethyl silyl deprotection is reported. Desired key intermediates, methyl 6-(3-triethyl silyloxy-5-oxocyclopent-1-enyl)hexanoate (4) and (E)-1-(tributylstannyl)-4-methyloct-1-en-4-yloxy)triethylsilane (5), were prepared from commercially available cycloheptanone and propargyl bromide, and the intermediates were coupled to obtain 3 in a convergent approach.

  DOI：

  10.1080/00397910802664228
• 作为产物：
  描述：

  methyl 7-(furan-2-yl)-7-hydroxyheptanoate 、 碘甲烷 在 zinc(II) chloride 、 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 methyl 6-(2-hydroxy-5-oxocyclopent-3-enyl)hexanoate
  参考文献：
  名称：

  Synthesis of 2-Normisoprostol, Methyl 6-(3-Hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)hexanoate

  摘要：

  Synthesis of 2-normisoprostol, methyl 6-(3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)hexanoate (3), employing two-component coupling strategy based on 1,4-addition followed by DDQ-mediated triethyl silyl deprotection is reported. Desired key intermediates, methyl 6-(3-triethyl silyloxy-5-oxocyclopent-1-enyl)hexanoate (4) and (E)-1-(tributylstannyl)-4-methyloct-1-en-4-yloxy)triethylsilane (5), were prepared from commercially available cycloheptanone and propargyl bromide, and the intermediates were coupled to obtain 3 in a convergent approach.

  DOI：

  10.1080/00397910802664228

文献信息

• Synthesis of 2-Normisoprostol, Methyl 6-(3-Hydroxy-2-((<i>E</i>)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)hexanoate
  作者：M. Harikrishna、H. Rama Mohan、P. K. Dubey、Gottumukkala V. Subbaraju

  DOI：10.1080/00397910802664228

  日期：2009.7.7

  Synthesis of 2-normisoprostol, methyl 6-(3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)hexanoate (3), employing two-component coupling strategy based on 1,4-addition followed by DDQ-mediated triethyl silyl deprotection is reported. Desired key intermediates, methyl 6-(3-triethyl silyloxy-5-oxocyclopent-1-enyl)hexanoate (4) and (E)-1-(tributylstannyl)-4-methyloct-1-en-4-yloxy)triethylsilane (5), were prepared from commercially available cycloheptanone and propargyl bromide, and the intermediates were coupled to obtain 3 in a convergent approach.