N-(4-pentenyl)iodoacetamide | 501435-49-0

• 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: N-(4-pentenyl)iodoacetamide
• 英文别名: Acetamide, 2-iodo-N-4-pentenyl-；2-iodo-N-pent-4-enylacetamide
• CAS: 501435-49-0
• 化学式: C₇H₁₂INO
• 分子量: 253.083
• InChiKey: DEEMBGBIBTYGFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-pentenyl)iodoacetamide 在 三乙基硼 、 三氟化硼 、 盐酸 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 以60%的产率得到5-(3-aminopropyl)dihydro-2(3H)-furanone hydrochloride
  参考文献：
  名称：

  去低聚：通过自由基低聚从不饱和酰胺制备内酰胺的新途径。

  摘要：

  [反应：参见文本] N-烯丙基或N-（3-丁烯基）碘乙酰胺的三乙基硼烷引发的原子转移自由基低聚，然后用盐酸处理，随后用K（2）CO（3）中和导致形成相应的5-羟基取代的δ-内酰胺或己内酰胺。该低聚-解聚序列可替代相应的分子内环化反应。

  DOI：

  10.1021/ol027428i

文献信息

• 8-Endo versus 7-Exo Cyclization of α-Carbamoyl Radicals. A Combination of Experimental and Theoretical Studies
  作者：Li Liu、Qian Chen、Yun-Dong Wu、Chaozhong Li

  DOI：10.1021/jo0481349

  日期：2005.3.1

  Atom transfer radical cyclization reactions of N-(4-pentenyl)iodoacetamides were investigated. The reactions were efficiently promoted by (BF3OEt2)-O-.. For N-alkenyl-substituted iodoamides, excellent regioselectivity in favor of 8-endo cyclization was observed, while both 7-exo and 8-endo cyclization products were formed with the 8-endo cyclization preferred in the cases of N-(2-allylphenyl)substituted iodoamides. Density functional theory calculations at the B3LYP/6-31G* level revealed that both the s-trans and the s-cis conformational transition structures were feasible for the 8-endo cyclization of N-alkenyl-substituted a-carbamoyl radicals while 7-exo transition structures were much less stable. For the cyclization of N-(2-allylphenyl)-substituted alpha-carbamoyl radicals, the transition structures for 8-endo and 7-exo cyclizations were of comparable energy. These results were in excellent agreement with the experimental observations.