(2S,3aS,4S,5R,6S)-5-(Acetyloxy)-4-(3,4-dimethoxyphenyl)-6-((R)-2,2-diphenylcyclopentoxy)-4-ethylhexahydroisoxazolo<2,3-b>oxazine-2-carboxylic acid methyl ester | 1053626-51-9

• 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: (2S,3aS,4S,5R,6S)-5-(Acetyloxy)-4-(3,4-dimethoxyphenyl)-6-((R)-2,2-diphenylcyclopentoxy)-4-ethylhexahydroisoxazolo<2,3-b>oxazine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3aS,4S,5R,6S)-5-acetyloxy-4-(3,4-dimethoxyphenyl)-6-[(1R)-2,2-diphenylcyclopentyl]oxy-4-ethyl-3,3a,5,6-tetrahydro-2H-[1,2]oxazolo[2,3-b]oxazine-2-carboxylate
• CAS: 1053626-51-9
• 化学式: C₃₇H₄₃NO₉
• 分子量: 645.75
• InChiKey: PNRYRQXSFJDGBK-GSSUSULBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3aS,4S,5R,6S)-5-(Acetyloxy)-4-(3,4-dimethoxyphenyl)-6-((R)-2,2-diphenylcyclopentoxy)-4-ethylhexahydroisoxazolo<2,3-b>oxazine-2-carboxylic acid methyl ester 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2R,6S,7R,7aR)-7-(3,4-Dimethoxy-phenyl)-7-ethyl-2,6-dihydroxy-hexahydro-pyrrolizin-3-one 、 Acetic acid (1S,2R,6S,7aS)-1-(3,4-dimethoxy-phenyl)-1-ethyl-6-hydroxy-5-oxo-hexahydro-pyrrolizin-2-yl ester
  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：

  (Z)-1-(Acetoxy)-2-((R)-2,2-diphenylcyclopentoxy)ethene 在 2,5-二叔丁基对苯二酚 、 四氯化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.5h， 生成 (2S,3aS,4S,5R,6S)-5-(Acetyloxy)-4-(3,4-dimethoxyphenyl)-6-((R)-2,2-diphenylcyclopentoxy)-4-ethylhexahydroisoxazolo<2,3-b>oxazine-2-carboxylic acid methyl ester
  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