rel-(3S,4S)-3-(Acetyloxy)-4-cyclohexyl-1-<(4-methylphenyl)sulfonyl>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: rel-(3S,4S)-3-(Acetyloxy)-4-cyclohexyl-1-<(4-methylphenyl)sulfonyl>pyrrolidine
• 英文别名: [(3S,4S)-4-cyclohexyl-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl] acetate
• 化学式: C₁₉H₂₇NO₄S
• 分子量: 365.494
• InChiKey: RCFQFICHXFOPDU-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 、 rel-(4R,5R,6S)-5-(Acetyloxy)-4-cyclohexyl-6--5,6-dihydro-3H-1,2-oxazine N-oxide 在 platinum(IV) oxide 氢气 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 1-(4-methylbenzenesulfonyl)-3-cyclohexylpyrrolidine 、 rel-(3S,4S)-3-(Acetyloxy)-4-cyclohexyl-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