N-[2-(2-bromophenyl)ethyl]-N-(2-(phenylthio)ethyl)acetamide | 848772-55-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-[2-(2-bromophenyl)ethyl]-N-(2-(phenylthio)ethyl)acetamide
• 英文别名: N-[2-(2-bromophenyl)ethyl]-N-(2-phenylsulfanylethyl)acetamide
• CAS: 848772-55-4
• 化学式: C₁₈H₂₀BrNOS
• 分子量: 378.333
• InChiKey: FHUPSYURTZZDBV-UHFFFAOYSA-N

物化性质

• 沸点：
  508.3±40.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-(2-bromophenyl)ethyl]-N-(2-(phenylthio)ethyl)acetamide 在 三正丁基氢锡 、 碳酸氢钠 、 间氯过氧苯甲酸 、 1,1'-偶氮(氰基环己烷) 作用下， 以 二氯甲烷 、 甲苯 、 xylene 为溶剂， 反应 17.0h， 生成 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：

  邻溴苯乙酸 在 硼烷四氢呋喃络合物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[2-(2-bromophenyl)ethyl]-N-(2-(phenylthio)ethyl)acetamide
  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.