9-[2]furyl-9-oxo-nonanoic acid methyl ester | 628298-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-[2]furyl-9-oxo-nonanoic acid methyl ester
• 英文别名: 9-[2]Furyl-9-oxo-nonansaeure-methylester；Methyl 9-(furan-2-yl)-9-oxononanoate；methyl 9-(furan-2-yl)-9-oxononanoate
• CAS: 628298-83-9
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: NOVPZNMUPUTVIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[2]furyl-9-oxo-nonanoic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 生成 Methyl 8-(3-hydroxy-5-oxocyclopenten-1-yl)octanoate
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042
• 作为产物：
  描述：

  3-(2-呋喃基)-3-氧代丙酸乙酯 在 氢氧化钾 、 乙醚 、 乙醇 、 sodium ethanolate 作用下， 生成 9-[2]furyl-9-oxo-nonanoic acid methyl ester
  参考文献：
  名称：

  Gruber, Chemische Berichte, 1955, vol. 88, p. 178,184

  摘要：

  DOI：

文献信息

• Gruber, Chemische Berichte, 1955, vol. 88, p. 178,184
  作者：Gruber

  DOI：——

  日期：——
• First total synthesis of the E type I phytoprostanes
  作者：Ana R. Rodrı́guez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2003.08.042

  日期：2003.9

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.