N-<(1-ethylthio)-5-hydroxy-5-(2-propenyl)-7-octenyl>-2,2-dimethylpropanamide | 131685-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-<(1-ethylthio)-5-hydroxy-5-(2-propenyl)-7-octenyl>-2,2-dimethylpropanamide
• CAS: 131685-00-2
• 化学式: C₁₈H₃₃NO₂S
• 分子量: 327.532
• InChiKey: QBIQNFXMJWOERE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  哌啶酮 在 对甲苯磺酸 N,N,N,N-tetraethylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-<(1-ethylthio)-5-hydroxy-5-(2-propenyl)-7-octenyl>-2,2-dimethylpropanamide
  参考文献：
  名称：

  Organometallic reactions of .omega.-heterosubstituted N-acyl lactams. A new route to .gamma.-keto aldehydes from 5-ethoxy-2-pyrrolidinone

  摘要：

  A new route to gamma-keto aldehydes has been developed in which 5-ethoxy-2-pyrrolidinone is the key intermediate, easily available from 2-pyrrolidinone or succinimide. The lactam undergoes the selective ring opening, previous ''in situ'' N-acylation reaction with pivaloyl chloride or di-tert-butyl dicarbonate and attack of Grignard reagents or pyridyllithium compounds, whereupon the gamma-keto aldehydes are produced by acidic hydrolysis. By this way the gamma-keto aldehydes, which are precursors of natural compounds, such as dihydrojasmone and methyl dihydrojasmonate, a feromone component of the peach fruit moth Carposina niponensis, and nicotine derivatives have been prepared. A practical synthesis of pyridyl-substituted pyrroles (alpha- and beta-nicotyrine and the nor derivatives) can be achieved without purification of the intermediates. N-Acylated 6-ethoxy-2-piperidinone is less reactive toward the organometallic attack, affording in low yields 5-phenyl-5-oxopentanal using phenylmagnesium chloride, and 2-pentylcyclohex-2-en-1-one using n-hexylmagnesium bromide.

  DOI：

  10.1021/jo00005a030

文献信息

• Organometallic reactions of .omega.-heterosubstituted N-acyl lactams. A new route to .gamma.-keto aldehydes from 5-ethoxy-2-pyrrolidinone
  作者：Diego Savoia、Vittorio Concialini、Sergio Roffia、Luca Tarsi

  DOI：10.1021/jo00005a030

  日期：1991.3

  A new route to gamma-keto aldehydes has been developed in which 5-ethoxy-2-pyrrolidinone is the key intermediate, easily available from 2-pyrrolidinone or succinimide. The lactam undergoes the selective ring opening, previous ''in situ'' N-acylation reaction with pivaloyl chloride or di-tert-butyl dicarbonate and attack of Grignard reagents or pyridyllithium compounds, whereupon the gamma-keto aldehydes are produced by acidic hydrolysis. By this way the gamma-keto aldehydes, which are precursors of natural compounds, such as dihydrojasmone and methyl dihydrojasmonate, a feromone component of the peach fruit moth Carposina niponensis, and nicotine derivatives have been prepared. A practical synthesis of pyridyl-substituted pyrroles (alpha- and beta-nicotyrine and the nor derivatives) can be achieved without purification of the intermediates. N-Acylated 6-ethoxy-2-piperidinone is less reactive toward the organometallic attack, affording in low yields 5-phenyl-5-oxopentanal using phenylmagnesium chloride, and 2-pentylcyclohex-2-en-1-one using n-hexylmagnesium bromide.