N-[2-(2-bromophenyl)ethyl]-N-ethenylacetamide | 848772-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(2-bromophenyl)ethyl]-N-ethenylacetamide
• CAS: 848772-61-2
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: VXFJXQRJVVACDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[2-(2-bromophenyl)ethyl]-N-ethenylacetamide 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以42%的产率得到1H-3-苯氮杂卓,3-乙酰基-2,3,4,5-四氢-
  参考文献：
  名称：

  7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines:  Concise Construction of a Cephalotaxine Skeleton

  摘要：

  Bu3SnH-mediated radical cyclizations of 2-(2-bromophenyl)N-ethenylacetamide gave 6-exo cyclization product 15 as the major product, whereas N-[2-(2-bromophenyl)ethyl]-N-ethenylamides gave almost exclusively 7-endo cyclization products. These results indicated that the position of the carbonyl group on enamide played an important role in deciding the course of the cyclization. The 7-endo selective cyclization was applied to concise construction of a cephalotaxine skeleton.

  DOI：

  10.1021/jo040264u
• 作为产物：
  描述：

  N-[2-(2-bromophenyl)ethyl]-2-(phenylthio)ethylamine 在 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 16.5h， 生成 N-[2-(2-bromophenyl)ethyl]-N-ethenylacetamide
  参考文献：
  名称：

  7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines:  Concise Construction of a Cephalotaxine Skeleton

  摘要：

  Bu3SnH-mediated radical cyclizations of 2-(2-bromophenyl)N-ethenylacetamide gave 6-exo cyclization product 15 as the major product, whereas N-[2-(2-bromophenyl)ethyl]-N-ethenylamides gave almost exclusively 7-endo cyclization products. These results indicated that the position of the carbonyl group on enamide played an important role in deciding the course of the cyclization. The 7-endo selective cyclization was applied to concise construction of a cephalotaxine skeleton.

  DOI：

  10.1021/jo040264u

文献信息

• 7-<i>endo</i> Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines:  Concise Construction of a Cephalotaxine Skeleton
  作者：Tsuyoshi Taniguchi、Atsuko Ishita、Masahiko Uchiyama、Osamu Tamura、Osamu Muraoka、Genzoh Tanabe、Hiroyuki Ishibashi

  DOI：10.1021/jo040264u

  日期：2005.3.1

  Bu3SnH-mediated radical cyclizations of 2-(2-bromophenyl)N-ethenylacetamide gave 6-exo cyclization product 15 as the major product, whereas N-[2-(2-bromophenyl)ethyl]-N-ethenylamides gave almost exclusively 7-endo cyclization products. These results indicated that the position of the carbonyl group on enamide played an important role in deciding the course of the cyclization. The 7-endo selective cyclization was applied to concise construction of a cephalotaxine skeleton.