4-(3-carbethoxypropyl)-3-methylene-1-oxaspiro<4.5>-2-decanone | 143063-26-7

• 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: 4-(3-carbethoxypropyl)-3-methylene-1-oxaspiro<4.5>-2-decanone
• 英文别名: 1-Oxaspiro[4.5]decane-4-butanoic acid, 3-methylene-2-oxo-, ethyl ester；ethyl 4-(3-methylidene-2-oxo-1-oxaspiro[4.5]decan-4-yl)butanoate
• CAS: 143063-26-7
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: WCAIUNVYUWAEFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-碘-丁酸乙酯 、 环己酮 、 iodomethane,iodozinc(1+) 、 丙炔酸乙酯 在 lithium chloride 、 锌 作用下， 生成 4-(3-carbethoxypropyl)-3-methylene-1-oxaspiro<4.5>-2-decanone
  参考文献：
  名称：

  New preparation of .alpha.-methylene-.gamma.-butyrolactones mediated by (iodomethyl)zinc iodide

  摘要：

  DOI：

  10.1021/ja00045a050

文献信息

• Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide
  作者：AchyuthaRao Sidduri、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00062a010

  日期：1993.5

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.
• New preparation of .alpha.-methylene-.gamma.-butyrolactones mediated by (iodomethyl)zinc iodide
  作者：AchyuthaRao Sidduri、Paul Knochel

  DOI：10.1021/ja00045a050

  日期：1992.9