(Z)-4-oxo-2-trimethylsilyl-pent-2-enenitrile | 339529-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-oxo-2-trimethylsilyl-pent-2-enenitrile
• 英文别名: (E)-4-oxo-2-trimethylsilylpent-2-enenitrile
• CAS: 339529-31-6
• 化学式: C₈H₁₃NOSi
• 分子量: 167.283
• InChiKey: UCQZPKXOWXUXEJ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 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：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-oxo-2-trimethylsilyl-pent-2-enenitrile 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以91%的产率得到(Z)-4-oxo-pent-2-enenitrile
  参考文献：
  名称：

  The exhaustive silylation of 5-nitro-pentan-2-one: novel processes and opportunities

  摘要：

  Treatment of 5-nitro-pentan-2-one (1) with Me3SiOTf/Et3N leads to initial silylation of the C(O)Me-group to give regioisomeric silyl enol ethers 2a and 2b followed by double silylation of the NO2-group furnishing a mixture of N,N-bis(silyloxy)enamine 4a and enoxime TMS ether 6. Employment of a large excess of Me3SiOTf/Et3N triggers a cascade of eliminations and silylations to give a mixture of (E)-4-trimethylsilyloxy-2-trimethylsilyl-pent2,4-dienenitrile (8) and 3-oxo-1-(1,1,1-trimethylsilyl)-1-cyclobutanecarbonitrile (9). The use of Me3SiCl/DBU changes the selectivity of silylation of 1 to give silyl nitronate 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00055-2
• 作为产物：
  描述：

  5-硝基-2-戊酮 在 silica gel 、 三乙胺 作用下， 以 二氯甲烷 、 Petroleum ether 为溶剂， 反应 26.5h， 生成 (Z)-4-oxo-2-trimethylsilyl-pent-2-enenitrile
  参考文献：
  名称：

  The exhaustive silylation of 5-nitro-pentan-2-one: novel processes and opportunities

  摘要：

  Treatment of 5-nitro-pentan-2-one (1) with Me3SiOTf/Et3N leads to initial silylation of the C(O)Me-group to give regioisomeric silyl enol ethers 2a and 2b followed by double silylation of the NO2-group furnishing a mixture of N,N-bis(silyloxy)enamine 4a and enoxime TMS ether 6. Employment of a large excess of Me3SiOTf/Et3N triggers a cascade of eliminations and silylations to give a mixture of (E)-4-trimethylsilyloxy-2-trimethylsilyl-pent2,4-dienenitrile (8) and 3-oxo-1-(1,1,1-trimethylsilyl)-1-cyclobutanecarbonitrile (9). The use of Me3SiCl/DBU changes the selectivity of silylation of 1 to give silyl nitronate 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00055-2

文献信息

• The exhaustive silylation of 5-nitro-pentan-2-one: novel processes and opportunities
  作者：Alexander A. Tishkov、Il'ya M. Lyapkalo、Sema L. Ioffe、Yuri A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1016/s0040-4020(01)00055-2

  日期：2001.3

  Treatment of 5-nitro-pentan-2-one (1) with Me3SiOTf/Et3N leads to initial silylation of the C(O)Me-group to give regioisomeric silyl enol ethers 2a and 2b followed by double silylation of the NO2-group furnishing a mixture of N,N-bis(silyloxy)enamine 4a and enoxime TMS ether 6. Employment of a large excess of Me3SiOTf/Et3N triggers a cascade of eliminations and silylations to give a mixture of (E)-4-trimethylsilyloxy-2-trimethylsilyl-pent2,4-dienenitrile (8) and 3-oxo-1-(1,1,1-trimethylsilyl)-1-cyclobutanecarbonitrile (9). The use of Me3SiCl/DBU changes the selectivity of silylation of 1 to give silyl nitronate 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.