(E)-5-(tert-butyldimethylsilyloxy)-1-(4-methyl-1-pentenyl)-1,5-dihydro-2-pyrrolone | 675106-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (E)-5-(tert-butyldimethylsilyloxy)-1-(4-methyl-1-pentenyl)-1,5-dihydro-2-pyrrolone
• 英文别名: 2-[tert-butyl(dimethyl)silyl]oxy-1-[(E)-4-methylpent-1-enyl]-2H-pyrrol-5-one
• CAS: 675106-47-5
• 化学式: C₁₆H₂₉NO₂Si
• 分子量: 295.497
• InChiKey: PPFFUKYXARSVOS-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-(tert-butyldimethylsilyloxy)-1-(4-methyl-1-pentenyl)-1,5-dihydro-2-pyrrolone 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.17h， 生成 (2Z)-4-methoxyimino-2-butenoic acid ((E)-4-methyl-1-pentenyl)amide
  参考文献：
  名称：

  Divergent and Stereocontrolled Synthesis of the Enamide Side Chains of Oximidines I/II/III, Salicylihalamides A/B, Lobatamides A/D, and CJ-12,950

  摘要：

  A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)and (Z)-vinyl iodides with a protected malelmide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.

  DOI：

  10.1021/ol036381d
• 作为产物：
  描述：

  碘仿 、 异戊醛 、 5-(tert-butyldimethylsilyloxy)-1,5-dihydro-2-pyrrolone 在 chromium dichloride 、 potassium phosphate 、 噻吩-2-甲酸亚铜(I) 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 27.0h， 以178.6 mg的产率得到(E)-5-(tert-butyldimethylsilyloxy)-1-(4-methyl-1-pentenyl)-1,5-dihydro-2-pyrrolone
  参考文献：
  名称：

  Divergent and Stereocontrolled Synthesis of the Enamide Side Chains of Oximidines I/II/III, Salicylihalamides A/B, Lobatamides A/D, and CJ-12,950

  摘要：

  A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)and (Z)-vinyl iodides with a protected malelmide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.

  DOI：

  10.1021/ol036381d

文献信息

• Divergent and Stereocontrolled Synthesis of the Enamide Side Chains of Oximidines I/II/III, Salicylihalamides A/B, Lobatamides A/D, and CJ-12,950
  作者：Robert S. Coleman、Pei-Hua Liu

  DOI：10.1021/ol036381d

  日期：2004.2.1

  A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)and (Z)-vinyl iodides with a protected malelmide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.