2-Methylprop-2-en-1-yl iodoacetate | 134836-79-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Methylprop-2-en-1-yl iodoacetate
• 英文别名: 2-methylprop-2-enyl 2-iodoacetate
• CAS: 134836-79-6
• 化学式: C₆H₉IO₂
• 分子量: 240.041
• InChiKey: YJRRFGNWQBJVPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-Methylprop-2-en-1-yl iodoacetate 在 三乙基硼 、 氧气 、 samarium diiodide 作用下， 以 正己烷 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 6.0h， 以80%的产率得到4-甲基-4-戊酸
  参考文献：
  名称：

  Self-Protection:  The Advantage of Radical Oligomeric Mixtures in Organic Synthesis

  摘要：

  Atom-transfer radical oligomers of allyl iodoacetates were converted to 4-pentenoic acids upon treatment with zinc. Reactions of the radical oligomers of various omega-alkenyl iodoacetates with Grignard reagents afforded the corresponding substituted tetrahydrofuran derivatives. These results indicated that radical oligomeric mixtures not only serve as versatile intermediates in organic synthesis, but also exhibit unique advantages in that the oligomeric mixtures are self-protected and the deoligomerization functions as the simultaneous deprotection.

  DOI：

  10.1021/jo035461s

文献信息

• Converting Radical Oligomers to a Single Product
  作者：Hui Yu、Tao Wu、Chaozhong Li

  DOI：10.1021/ja026744p

  日期：2002.9.1

  Atom-transfer radical oligomerizations of omega-alkenyl iodoacetates followed by rearrangemental deoligomerization via treatment with concentrated H2SO4 or heating led to the formations of gamma-lactones in high yield, demonstrating the important value of radical oligomers in organic synthesis.
• Self-Protection:  The Advantage of Radical Oligomeric Mixtures in Organic Synthesis
  作者：Hui Yu、Chaozhong Li

  DOI：10.1021/jo035461s

  日期：2004.1.1

  Atom-transfer radical oligomers of allyl iodoacetates were converted to 4-pentenoic acids upon treatment with zinc. Reactions of the radical oligomers of various omega-alkenyl iodoacetates with Grignard reagents afforded the corresponding substituted tetrahydrofuran derivatives. These results indicated that radical oligomeric mixtures not only serve as versatile intermediates in organic synthesis, but also exhibit unique advantages in that the oligomeric mixtures are self-protected and the deoligomerization functions as the simultaneous deprotection.