3-(3',4'-dimethoxyphenyl)-3-ethyl-N-(p-tolylsulfonyl)pyrrolidine

• 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: 3-(3',4'-dimethoxyphenyl)-3-ethyl-N-(p-tolylsulfonyl)pyrrolidine
• 英文别名: 3-(3,4-Dimethoxyphenyl)-3-ethyl-1-(p-tolylsulfonyl)pyrrolidine；3-(3,4-dimethoxyphenyl)-3-ethyl-1-(4-methylphenyl)sulfonylpyrrolidine
• 化学式: C₂₁H₂₇NO₄S
• 分子量: 389.516
• InChiKey: XVILPSRWJHSAHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-1-nitro-2-(3',4'-dimethoxyphenyl)-1-butene 在 platinum(IV) oxide 氢气 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 25.0 ℃ 、1.1 MPa 条件下， 反应 26.0h， 生成 3-(3',4'-dimethoxyphenyl)-3-ethyl-N-(p-tolylsulfonyl)pyrrolidine
  参考文献：
  名称：

  Nitroalkene [4+2] cycloaddition as a general and stereoselective route to the synthesis of 3,3- and 3,4-disubstituted pyrrolidines

  摘要：

  2,2-Disubstituted 1-nitroalkenes 12 undergo Lewis acid-promoted [4 + 2] cycloadditions with n-butyl vinyl ether to afford cyclic nitronates 14 as anomeric mixtures in good yields. The resulting nitronates were reduced with hydrogen in the presence of Adam's catalyst to afford 3,3-disubstituted pyrrolidines which were isolated in good yield as their N-p-toluenesulfonamides 17. Cycloadditions of (E)-2-nitrostyrene with ethyl (E)- and (Z)-1-propenyl ethers provided for the stereoselective synthesis of cis- and trans-3-phenyl-4-methyl-N-(p-tolylsulfonyl)pyrrolidine. Similarly, trans-3,4-diphenyl-N-(p-tolysulfonyl)pyrrolidine was prepared from (E)-2-nitrostyrene and ethyl (E)-2-styryl ether.

  DOI：

  10.1021/jo00067a017

文献信息

• Nitroalkene [4+2] cycloaddition as a general and stereoselective route to the synthesis of 3,3- and 3,4-disubstituted pyrrolidines
  作者：Scott E. Denmark、Lawrence R. Marcin

  DOI：10.1021/jo00067a017

  日期：1993.7

  2,2-Disubstituted 1-nitroalkenes 12 undergo Lewis acid-promoted [4 + 2] cycloadditions with n-butyl vinyl ether to afford cyclic nitronates 14 as anomeric mixtures in good yields. The resulting nitronates were reduced with hydrogen in the presence of Adam's catalyst to afford 3,3-disubstituted pyrrolidines which were isolated in good yield as their N-p-toluenesulfonamides 17. Cycloadditions of (E)-2-nitrostyrene with ethyl (E)- and (Z)-1-propenyl ethers provided for the stereoselective synthesis of cis- and trans-3-phenyl-4-methyl-N-(p-tolylsulfonyl)pyrrolidine. Similarly, trans-3,4-diphenyl-N-(p-tolysulfonyl)pyrrolidine was prepared from (E)-2-nitrostyrene and ethyl (E)-2-styryl ether.