(E)-2-(Ethylsulfinyl)-1-nitro-1-propene | 155880-61-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E)-2-(Ethylsulfinyl)-1-nitro-1-propene
• 英文别名: (E)-2-ethylsulfinyl-1-nitroprop-1-ene
• CAS: 155880-61-8
• 化学式: C₅H₉NO₃S
• 分子量: 163.197
• InChiKey: GKQJXJDSYJWFPB-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 (E)-2-(Ethylsulfinyl)-1-nitro-1-propene 在 zinc(II) iodide 作用下， 反应 15.0h， 生成 (1R,4S,5R,6R)-5-Ethanesulfinyl-5-methyl-6-nitro-bicyclo[2.2.1]hept-2-ene 、 (1S,4R,5R,6R)-5-Ethanesulfinyl-5-methyl-6-nitro-bicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Diastereoselective Diels-Alder Cycloadditions with Chiral 1-(Alkylsulfinyl)-2-nitroalkenes

  摘要：

  Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric [4 + 2] cycloaddition. Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids. Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing [4 + 2] cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.

  DOI：

  10.1021/jo00087a043
• 作为产物：
  描述：

  (E)-2-(Ethylthio)-1-nitro-1-propene 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以91%的产率得到(E)-2-(Ethylsulfinyl)-1-nitro-1-propene
  参考文献：
  名称：

  Diastereoselective Diels-Alder Cycloadditions with Chiral 1-(Alkylsulfinyl)-2-nitroalkenes

  摘要：

  Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric [4 + 2] cycloaddition. Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids. Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing [4 + 2] cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.

  DOI：

  10.1021/jo00087a043