ethyl 2-acetyl-6-iodo-2-methylhexanoate | 105666-04-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-acetyl-6-iodo-2-methylhexanoate
• 英文别名: Ethyl 2-(4-iodobutyl)-2-methyl-3-oxobutanoate
• CAS: 105666-04-4
• 化学式: C₁₁H₁₉IO₃
• 分子量: 326.175
• InChiKey: FFCWQKPILOYNRL-UHFFFAOYSA-N

物化性质

• 沸点：
  326.2±32.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetyl-6-iodo-2-methylhexanoate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到ethyl 6-iodo-2-(1-hydroxyethyl)-2-methylhexanoate
  参考文献：
  名称：

  Stereocontrolled cyclization reactions mediated by samarium diiodide

  摘要：

  DOI：

  10.1021/ja00236a025

文献信息

• Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00077a053

  日期：1993.12

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.