tetrahydro-6-(3-iodopropyl)-2H-pyran-2-one | 98560-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tetrahydro-6-(3-iodopropyl)-2H-pyran-2-one
• 英文别名: 5-(3-Iodopropyl)-5-pentanolide；6-(3-Iodopropyl)oxan-2-one
• CAS: 98560-11-3
• 化学式: C₈H₁₃IO₂
• 分子量: 268.095
• InChiKey: DABSLCWBFXGLKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydro-6-(3-iodopropyl)-2H-pyran-2-one 在 tris(dibenzoylmethano)iron(III) samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到9-oxabicyclo[3.3.1]nonan-1-ol
  参考文献：
  名称：

  Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents

  摘要：

  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.

  DOI：

  10.1021/jo00077a053
• 作为产物：
  描述：

  cyclooctane-1,5-diol 在 sodium tetrahydroborate 、 Celite 、 碘 、 pyridinium chlorochromate 、 mercury(II) oxide 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 29.0h， 生成 tetrahydro-6-(3-iodopropyl)-2H-pyran-2-one
  参考文献：
  名称：

  基于跨环半缩醛产生的烷氧基的区域选择性β-断裂，获得γ-取代的γ-内酯和δ-取代的δ-内酯的新途径

  摘要：

  描述了包括天然的信息素二氢-5-辛基-2（3 H）-呋喃酮在内的γ-取代的γ-内酯和δ-取代的δ-内酯的新的一般合成。合成涉及从环过半缩醛产生的烷氧基的区域选择性β-断裂作为关键步骤。

  DOI：

  10.1016/s0040-4020(01)89727-1

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.
• A new route to γ-substituted γ-lactones and δ-substituted δ-lactones based on the regioselective β-scission of alkoxyl radicals generated from transannular hemiacetals
  作者：Kazuhiro Kobayashi、Akiyoshi Sasaki、Yoshikazu Kanno、Hiroshi Suginome

  DOI：10.1016/s0040-4020(01)89727-1

  日期：1991.8

  A new general synthesis of γ-substituted γ-lactones and δ-substituted δ-lactones including dihydro-5-octyl-2(3H)-furanone, a natural pheromone, is described. The synthesis involves the regioselective β-scission of alkoxyl radicals generated from transannular hemiacetals as the key step.

  描述了包括天然的信息素二氢-5-辛基-2（3 H）-呋喃酮在内的γ-取代的γ-内酯和δ-取代的δ-内酯的新的一般合成。合成涉及从环过半缩醛产生的烷氧基的区域选择性β-断裂作为关键步骤。