2-(ethylsulfonyl)-1-nitroethylene | 136399-32-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-(ethylsulfonyl)-1-nitroethylene
• 英文别名: 1-nitro-2-ethylsulfonylethene；1-Ethylsulfonyl-2-nitroethene
• CAS: 136399-32-1
• 化学式: C₄H₇NO₄S
• 分子量: 165.17
• InChiKey: WLUKOXBOLNARQN-UHFFFAOYSA-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：
  0.5
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(ethylsulfonyl)-1-nitroethylene 、 1-bromohexyl acetate 在 lithium chloride 、 锌 作用下， 生成 1-pentyl-3-nitro-2-propenyl acetate
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010
• 作为产物：
  描述：

  在 溴 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以15%的产率得到1-nitro-1,2-dibromo-2-ethylsulfonylethene
  参考文献：
  名称：

  Mukhina, E. S.; Pavlova, Z. F.; Nekrasova, G. V., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 11, p. 1973 - 1977

  摘要：

  DOI：