1-(tert-butoxycarbonyl)-5-ethoxy-1-azacyclopentanone | 131684-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(tert-butoxycarbonyl)-5-ethoxy-1-azacyclopentanone
• 英文别名: Tert-butyl 2-ethoxy-5-oxopyrrolidine-1-carboxylate；tert-butyl 2-ethoxy-5-oxopyrrolidine-1-carboxylate
• CAS: 131684-97-4
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: WAYDKKSXCOXFKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.5±35.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴吡啶 、 1-(tert-butoxycarbonyl)-5-ethoxy-1-azacyclopentanone 在 正丁基锂 作用下， 生成 4-氧代-4-(3-吡啶基)丁醛
  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
• 作为产物：
  描述：

  5-乙氧基-2-吡咯烷酮 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.8h， 以95%的产率得到1-(tert-butoxycarbonyl)-5-ethoxy-1-azacyclopentanone
  参考文献：
  名称：

  酰胺与碳酸氢二叔丁酯反应的底物酸度和转化时间

  摘要：

  酰胺与四碳酸二叔丁酯的4-二甲基氨基吡啶催化的转化时间随底物酸度的变化而变化。的pK一个的在一些酰胺的DMSO被确定为与底物的反应性酸度的支持相关性。特别是酸性的底物，例如4-噻唑烷酮，很容易与各种二碳酸二烷基酯反应。酸性较低的底物与Boc 2 O反应，但其他二碳酸二烷基酯优先分解。

  DOI：

  10.1016/0040-4039(95)01931-7

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.
• Substrate acidities and conversion times for reactions of amides with di-tert-butyl bicarbonate
  作者：Marvin M. Hansen、Allen R. Harkness、D. Scott Coffey、Frederick G. Bordwell、Yongyu Zhao

  DOI：10.1016/0040-4039(95)01931-7

  日期：1995.12

  The conversion time tor 4-dimethylaminopyndine catalysed reaction of amides with di-tert-butyl dicarbonate varies dramatically with substrate acidity. The pKa's in DMSO of some amides are determined to support correlation of reactivity with substrate acidity. Particularly acidic substrates, such as 4-thiazolidinone, readily react with a variety of dialkyl dicarbonates. Less acidic substrates react

  酰胺与四碳酸二叔丁酯的4-二甲基氨基吡啶催化的转化时间随底物酸度的变化而变化。的pK一个的在一些酰胺的DMSO被确定为与底物的反应性酸度的支持相关性。特别是酸性的底物，例如4-噻唑烷酮，很容易与各种二碳酸二烷基酯反应。酸性较低的底物与Boc 2 O反应，但其他二碳酸二烷基酯优先分解。