4-(3,4-Dimethoxyphenyl)-4-ethyl-1-<(4-methylphenyl)sulfonyl>-3-pyrrolidinone | 156908-19-9

• 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: 4-(3,4-Dimethoxyphenyl)-4-ethyl-1-<(4-methylphenyl)sulfonyl>-3-pyrrolidinone
• 英文别名: 4-(3,4-dimethoxyphenyl)-4-ethyl-1-(4-methylphenyl)sulfonylpyrrolidin-3-one
• CAS: 156908-19-9
• 化学式: C₂₁H₂₅NO₅S
• 分子量: 403.499
• InChiKey: QXKMUMYVXOWFBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3,4-Dimethoxyphenyl)-4-ethyl-1-<(4-methylphenyl)sulfonyl>-3-pyrrolidinone 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 rel-(3R,4R)-3-(Acetyloxy)-4-(3,4-dimethoxyphenyl)-4-ethyl-1-<(4-methylphenyl)sulfonyl>pyrrolidine
  参考文献：
  名称：

  Nitroalkene [4 + 2] Cycloadditions with 2-(Acyloxy)vinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-substituted-pyrrolidines

  摘要：

  2-(Acyloxy)vinyl ethers undergo regioselective [4 + 2] cycloadditions with nitroalkenes (promoted by SnCl4) to afford subsutituted 5-acetoxy nitronates in good yields (68-91%). Endo/exo selectivity in the cycloadditions has been found to be dependent on the nitroalkene substitution; 2-aryl-1-nitroalkenes provided exclusively exo cycloadducts while 2-cyclohexyl-1-nitroalkene 28 afforded predominately endo cycloadducts in a ratio of 12:1. The resulting nitronates can be elaborated to N-tosyl-4-substituted-3-hydroxypyrrolidines by hydrogenolysis (160 psi of H-2/PtO2) or to bicyclic alpha-hydroxy lactams by [3 + 2] cycloaddition followed by hydrogenation (14.7 psi of H-2/Raney nickel). A chiral 2-acetoxyvinyl ether derived from (R)-2,2-diphenylcyclopentanol has been employed in the cycloaddition-hydrogenation sequence to prepare an optically active N-tosyl-3-hydroxypyrrolidine in 96% ee.

  DOI：

  10.1021/jo00095a038
• 作为产物：
  描述：

  (E)-1-nitro-2-(3',4'-dimethoxyphenyl)-1-butene 在 platinum(IV) oxide 4 A molecular sieve 、 氢气 、 四氯化锡 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 43.0h， 生成 4-(3,4-Dimethoxyphenyl)-4-ethyl-1-<(4-methylphenyl)sulfonyl>-3-pyrrolidinone
  参考文献：
  名称：

  Nitroalkene [4 + 2] Cycloadditions with 2-(Acyloxy)vinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-substituted-pyrrolidines

  摘要：

  2-(Acyloxy)vinyl ethers undergo regioselective [4 + 2] cycloadditions with nitroalkenes (promoted by SnCl4) to afford subsutituted 5-acetoxy nitronates in good yields (68-91%). Endo/exo selectivity in the cycloadditions has been found to be dependent on the nitroalkene substitution; 2-aryl-1-nitroalkenes provided exclusively exo cycloadducts while 2-cyclohexyl-1-nitroalkene 28 afforded predominately endo cycloadducts in a ratio of 12:1. The resulting nitronates can be elaborated to N-tosyl-4-substituted-3-hydroxypyrrolidines by hydrogenolysis (160 psi of H-2/PtO2) or to bicyclic alpha-hydroxy lactams by [3 + 2] cycloaddition followed by hydrogenation (14.7 psi of H-2/Raney nickel). A chiral 2-acetoxyvinyl ether derived from (R)-2,2-diphenylcyclopentanol has been employed in the cycloaddition-hydrogenation sequence to prepare an optically active N-tosyl-3-hydroxypyrrolidine in 96% ee.

  DOI：

  10.1021/jo00095a038

文献信息

• Denmark Scott E., Schnute Mark E., J. Org. Chem, 59 (1994) N 16, S 4576-4595
  作者：Denmark Scott E., Schnute Mark E.

  DOI：——

  日期：——