methyl 4-iodobicyclo<2.2.1>heptane-1-carboxylate | 123463-12-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 4-iodobicyclo<2.2.1>heptane-1-carboxylate
• 英文别名: Methyl 4-iodobicyclo[2.2.1]heptane-1-carboxylate
• CAS: 123463-12-7
• 化学式: C₉H₁₃IO₂
• 分子量: 280.106
• InChiKey: PTTJFMDUWQLFIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 0.5 Torr)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  methyl 4-iodobicyclo<2.2.1>heptane-1-carboxylate 在 氢氧化钾 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 双环[2.2.1]庚烷-1-羧酸
  参考文献：
  名称：

  A Reinvestigation of the Trimethylstannylation of 1-Iodonorbornane: Competition between Polar and Radical Pathways

  摘要：

  DOI：

  10.1021/jo00108a041
• 作为产物：
  描述：

  4-(甲氧基羰基)双环[2.2.1]庚烷-1-甲酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 2-碘-1,1,1-三氟乙烷 、 2-mercaptopyridine-1-oxide sodium salt 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 methyl 4-iodobicyclo<2.2.1>heptane-1-carboxylate
  参考文献：
  名称：

  Synthesis of bridgehead fluorides by fluorodeiodination

  摘要：

  Fluorodeiodination is found to be an attractive procedure for the synthesis of bridgehead fluorides. Thus, treatment of the corresponding iodide with xenon difluoride in dichloromethane at ambient temperature generally leads to high yields of the fluoride. Evidence suggests the intermediacy of the bridgehead cation in this reaction, and accordingly the substrates which are unfavorably disposed to fluorodeiodination are the bicyclo[n.1.1]alkyl iodides. In this context the isolation of a small quantity of methyl 4-fluorobicyclo[2.1.1]hexane-1-carboxylate (46, R = COOMe) is significant because it represents the first occasion on which the elusive 1-bicyclo[2.1.1]hexyl cation has been trapped. We have also demonstrated that synthesis of the iodides themselves can be accomplished efficiently both by Barton halodecarboxylation and by treatment of the carboxylic acid with lead tetraacetate and iodine.

  DOI：

  10.1021/jo00036a018

文献信息

• Mechanistic definition of trimethylstannylation of 1,4-dihalobicyclo[2.2.1]heptanes: bridgehead nucleophilic substitution mediated by the intermediacy of radicals, radical anions, carbanions, and [2.2.1.]propellane
  作者：William Adcock、Hemakanthi Gangodawila

  DOI：10.1021/jo00287a014

  日期：1989.12
• ADCOCK, WILLIAM;GANGODAWILA, HEMAKANTHI, J. ORG. CHEM., 54,(1989) N6, C. 6040-6047
  作者：ADCOCK, WILLIAM、GANGODAWILA, HEMAKANTHI

  DOI：——

  日期：——
• Synthesis of bridgehead fluorides by fluorodeiodination
  作者：Ernest W. Della、Nicholas J. Head

  DOI：10.1021/jo00036a018

  日期：1992.5

  Fluorodeiodination is found to be an attractive procedure for the synthesis of bridgehead fluorides. Thus, treatment of the corresponding iodide with xenon difluoride in dichloromethane at ambient temperature generally leads to high yields of the fluoride. Evidence suggests the intermediacy of the bridgehead cation in this reaction, and accordingly the substrates which are unfavorably disposed to fluorodeiodination are the bicyclo[n.1.1]alkyl iodides. In this context the isolation of a small quantity of methyl 4-fluorobicyclo[2.1.1]hexane-1-carboxylate (46, R = COOMe) is significant because it represents the first occasion on which the elusive 1-bicyclo[2.1.1]hexyl cation has been trapped. We have also demonstrated that synthesis of the iodides themselves can be accomplished efficiently both by Barton halodecarboxylation and by treatment of the carboxylic acid with lead tetraacetate and iodine.
• A Reinvestigation of the Trimethylstannylation of 1-Iodonorbornane: Competition between Polar and Radical Pathways
  作者：William Adcock、Christopher I. Clark

  DOI：10.1021/jo00108a041

  日期：1995.2