methyl 6-(3-triethylsilyloxy-5-oxocyclopent-1-enyl)hexanoate | 1184292-14-5

• 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-(3-triethylsilyloxy-5-oxocyclopent-1-enyl)hexanoate
• 英文别名: Methyl 6-(5-oxo-3-triethylsilyloxycyclopenten-1-yl)hexanoate
• CAS: 1184292-14-5
• 化学式: C₁₈H₃₂O₄Si
• 分子量: 340.535
• InChiKey: IARAKPQUADSHCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-(3-triethylsilyloxy-5-oxocyclopent-1-enyl)hexanoate 、 4-Methyl-1-octin-4(RS)-ol-triethylsilylether 在 偶氮二异丁腈 、 三正丁基氢锡 、 甲基锂 、 copper(l) cyanide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以3.8 g的产率得到methyl 6-(3-triethylsilyloxy-2-((E)-4-triethylsilyloxy-4-methyloct-1-enyl)-5-oxocyclopentyl)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：

  三乙基氯硅烷 、 methyl 6-(3-hydroxy-5-oxocyclopent-1-enyl)hexanoate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到methyl 6-(3-triethylsilyloxy-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

文献信息

• KALISH, VINCENT J.;SHONE, ROBERT L.;KRAMER, STEVEN W.;COLLINS, PAUL W.;BA+, SYNTH. COMMUN., 20,(1990) N1, C. 1641-1645
  作者：KALISH, VINCENT J.、SHONE, ROBERT L.、KRAMER, STEVEN W.、COLLINS, PAUL W.、BA+

  DOI：——

  日期：——
• 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.