2-(2-bromophenyl)-N-ethyl-N-(2-(phenylsulfinyl)ethyl)acetamide | 848772-84-9

• 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: 2-(2-bromophenyl)-N-ethyl-N-(2-(phenylsulfinyl)ethyl)acetamide
• 英文别名: N-[2-(benzenesulfinyl)ethyl]-2-(2-bromophenyl)-N-ethylacetamide
• CAS: 848772-84-9
• 化学式: C₁₈H₂₀BrNO₂S
• 分子量: 394.332
• InChiKey: KMFXSSPVVQVALM-UHFFFAOYSA-N

物化性质

• 沸点：
  564.6±40.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  56.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-N-ethyl-N-(2-(phenylsulfinyl)ethyl)acetamide 在 三正丁基氢锡 、 碳酸氢钠 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 、 xylene 为溶剂， 反应 15.0h， 生成 3-ethyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one
  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 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-(2-bromophenyl)-N-ethyl-N-(2-(phenylsulfinyl)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

• Photoredox Catalytic Access to <i>N</i>,<i>O</i>‐Acetals from Enamides by Means of Electron‐Poor Perylene Bisimides
  作者：Desirée Steuernagel、David Rombach、Hans‐Achim Wagenknecht

  DOI：10.1002/chem.202400247

  日期：——

  Enamides can be converted into their N,O-acetals using just electron-poor perylene bisimides together with light, without the need for thiophenol as additive or strong acids as catalyst.

  仅使用缺电子苝双酰亚胺和光即可将烯酰胺转化为N , O-缩醛，无需苯硫酚作为添加剂或强酸作为催化剂。
• 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.