tert-butyl-[(E)-1-chloro-3-methyl-2-nitronon-2-enyl]-dimethylsilane | 1448196-12-0

• 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: tert-butyl-[(E)-1-chloro-3-methyl-2-nitronon-2-enyl]-dimethylsilane
• CAS: 1448196-12-0
• 化学式: C₁₆H₃₂ClNO₂Si
• 分子量: 333.974
• InChiKey: MPPNOUDXJWYEEB-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 Iron(III) nitrate nonahydrate 、 iron(III) chloride hexahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 tert-butyl-[(Z)-1-chloro-3-methyl-2-nitronon-2-enyl]-dimethylsilane 、 tert-butyl-[(E)-1-chloro-3-methyl-2-nitronon-2-enyl]-dimethylsilane 、
  参考文献：
  名称：

  Nitration of Silyl Allenes To Form Functionalized Nitroalkenes

  摘要：

  An efficient nitration of silyl allenes with nitrogen dioxide radical, generated from NaNO2 and AcOH, to form alpha-nitro-alpha,beta-unsaturated silyl oximes has been developed. A similar nitration could be achieved by using Fe(NO3)(3)center dot 9H(2)O and FeCl3 center dot 6H(2)O, but different from the regioselective oxime formation, two regioisomeric chloride-trapped products were isolated with varying ratios depending on the steric bulk of the silyl group. A novel ring-closure reaction of alpha-nitro-alpha,beta-unsaturated silyl oximes upon treating with TBAF to form isooxazolidinone derivatives was also developed.

  DOI：

  10.1021/ol401735v

文献信息

• Nitration of Silyl Allenes To Form Functionalized Nitroalkenes
  作者：Venkata R. Sabbasani、Daesung Lee

  DOI：10.1021/ol401735v

  日期：2013.8.2

  An efficient nitration of silyl allenes with nitrogen dioxide radical, generated from NaNO2 and AcOH, to form alpha-nitro-alpha,beta-unsaturated silyl oximes has been developed. A similar nitration could be achieved by using Fe(NO3)(3)center dot 9H(2)O and FeCl3 center dot 6H(2)O, but different from the regioselective oxime formation, two regioisomeric chloride-trapped products were isolated with varying ratios depending on the steric bulk of the silyl group. A novel ring-closure reaction of alpha-nitro-alpha,beta-unsaturated silyl oximes upon treating with TBAF to form isooxazolidinone derivatives was also developed.