3-butenyl iodoacetate | 129352-57-4

• 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: 3-butenyl iodoacetate
• 英文别名: But-3-enyl 2-iodoacetate
• CAS: 129352-57-4
• 化学式: C₆H₉IO₂
• 分子量: 240.041
• InChiKey: ATLWVPWBYIRWES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  5
• 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：

  3-butenyl iodoacetate 在 三乙基硼 、 氧气 、 硫酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 以73%的产率得到5-(2-Iodo-ethyl)-dihydro-furan-2-one
  参考文献：
  名称：

  Converting Radical Oligomers to a Single Product

  摘要：

  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.

  DOI：

  10.1021/ja026744p

文献信息

• Powerful Solvent Effect of Water in Radical Reaction:  Triethylborane-Induced Atom-Transfer Radical Cyclization in Water
  作者：Hideki Yorimitsu、Tomoaki Nakamura、Hiroshi Shinokubo、Koichiro Oshima、Kiyoyuki Omoto、Hiroshi Fujimoto

  DOI：10.1021/ja0014281

  日期：2000.11.1

  γ-lactone in high yield. The remarkable solvent effect of water was observed in this reaction, although the medium effect is believed to be small in radical reactions. Powerful solvent effects also operate in the preparation of medium- and large-ring lactones. Water as a reaction solvent strikingly promoted the cyclization reaction of large-membered rings. Stirring a solution of 3,6-dioxa-8-nonenyl iodoacetate

  描述了三乙基硼烷诱导的碘缩醛和碘乙酸酯在水中的原子转移自由基环化。碘缩醛的自由基环化反应在甲醇水溶液和水中都能顺利进行。碘乙酸烯丙酯 (3a) 的原子转移自由基环化在水中比在苯或己烷中更有效。例如，在室温下在苯或己烷中用三乙基硼烷处理 3a 不会产生所需的内酯。相比之下，3a 在水中环化得更顺利，并以高产率产生相应的 γ-内酯。在该反应中观察到水的显着溶剂效应，尽管认为在自由基反应中中等效应很小。强大的溶剂效应也可用于制备中环和大环内酯。水作为反应溶剂显着促进了大元环的环化反应。在三乙基硼烷存在下，在 25°C 下搅拌 3,6-二氧杂-8-壬烯基碘乙酸酯在水中的溶液 10 小时，提供了一个...
• Radical cyclizatations of α-fluoro-α-iodo and α-iodo esters and amides.
  作者：Francis Barth、Counde O-Yang

  DOI：10.1016/s0040-4039(00)88741-9

  日期：1990.1
• 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.
• Triethylborane-Mediated Atom Transfer Radical Cyclization Reaction in Water
  作者：Hideki Yorimitsu、Tomoaki Nakamura、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo981774p

  日期：1998.11.1
• BARTH, FRANCIS;O-YANG, COUNDE, TETRAHEDRON LETT., 31,(1990) N, C. 1121-1124
  作者：BARTH, FRANCIS、O-YANG, COUNDE

  DOI：——

  日期：——