5-(4-chloro-phenyl)-3-oxo-5-(toluene-4-sulfonylamino)-pentanoic acid ethyl ester | 942301-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-chloro-phenyl)-3-oxo-5-(toluene-4-sulfonylamino)-pentanoic acid ethyl ester
• 英文别名: Ethyl 5-(4-chlorophenyl)-5-[(4-methylphenyl)sulfonylamino]-3-oxopentanoate；ethyl 5-(4-chlorophenyl)-5-[(4-methylphenyl)sulfonylamino]-3-oxopentanoate
• CAS: 942301-16-8
• 化学式: C₂₀H₂₂ClNO₅S
• 分子量: 423.917
• InChiKey: VVYWCHVYQAZFLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-chloro-phenyl)-3-oxo-5-(toluene-4-sulfonylamino)-pentanoic acid ethyl ester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 生成 N-{1-(4-chloro-phenyl)-2-[2-(2-hydroxy-ethyl)-[1,3]dioxolan-2-yl]-ethyl}-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Regioselective addition of 1,3-dicarbonyl dianion to N-sulfonyl aldimines: an expedient route to N-sulfonyl piperidines and N-sulfonyl azetidines

  摘要：

  A simple route for the synthesis of delta-amino-beta-keto esters and delta-amino-beta-diketones is reported. This involves regioselective addition of 1,3-dianions derived from ethyl acetoacetate and acetyl acetone to N-sulfonyl aldimines. The delta-amino-beta-keto ester derivatives were further converted into the corresponding N-sulfonyl piperidines and N-sulfonyl azetidines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.081
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到5-(4-chloro-phenyl)-3-oxo-5-(toluene-4-sulfonylamino)-pentanoic acid ethyl ester
  参考文献：
  名称：

  Regioselective addition of 1,3-dicarbonyl dianion to N-sulfonyl aldimines: an expedient route to N-sulfonyl piperidines and N-sulfonyl azetidines

  摘要：

  A simple route for the synthesis of delta-amino-beta-keto esters and delta-amino-beta-diketones is reported. This involves regioselective addition of 1,3-dianions derived from ethyl acetoacetate and acetyl acetone to N-sulfonyl aldimines. The delta-amino-beta-keto ester derivatives were further converted into the corresponding N-sulfonyl piperidines and N-sulfonyl azetidines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.081

文献信息

• Regioselective addition of 1,3-dicarbonyl dianion to N-sulfonyl aldimines: an expedient route to N-sulfonyl piperidines and N-sulfonyl azetidines
  作者：Manas K. Ghorai、Amit Kumar、Sandipan Halder

  DOI：10.1016/j.tet.2007.03.081

  日期：2007.5

  A simple route for the synthesis of delta-amino-beta-keto esters and delta-amino-beta-diketones is reported. This involves regioselective addition of 1,3-dianions derived from ethyl acetoacetate and acetyl acetone to N-sulfonyl aldimines. The delta-amino-beta-keto ester derivatives were further converted into the corresponding N-sulfonyl piperidines and N-sulfonyl azetidines. (C) 2007 Elsevier Ltd. All rights reserved.