(3S,6R,7aR)-6-Allyl-6-methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one | 155627-28-4

• 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: (3S,6R,7aR)-6-Allyl-6-methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
• 英文别名: (3S,6R,7aR)-6-methyl-3-phenyl-6-prop-2-enyl-2,3,7,7a-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 155627-28-4
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: BVXXPNSIHLYCPL-IIAWOOMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,6R,7aR)-6-Allyl-6-methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 30.0h， 生成 (R)-3-Methyl-3-propyl-pyrrolidine
  参考文献：
  名称：

  A Synthesis of Enantiomerically Pure 3- and 3,3-Disubstituted Pyrrolidines

  摘要：

  Enantiomerically pure bicyclic lactam 1, derived from (S)-phenylglycinol, underwent diastereoselective mono- and dialkylation affording substituted lactams 2 and 3 bearing tertiary and quaternary stereocenters. Reduction with LiAlH4 furnished N-(2'-hydroxy-1'-phenylethyl) pyrrolidines 4 which were efficiently debenzylated by catalytic hydrogenolysis to afford enantiomerically pure 3-mono- and 3,3-disubstituted pyrrolidines 5.

  DOI：

  10.1016/s0040-4039(00)79942-4
• 作为产物：
  描述：

  (3S-顺式)-(-)-3-苯基四氢吡咯并-[2,1-b]-恶唑-5(6H)-酮 、 3-溴丙烯 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 生成 (3S,6R,7aR)-6-Allyl-6-methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 、 (3S,6S,7aR)-6-Allyl-6-methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
  参考文献：
  名称：

  A Synthesis of Enantiomerically Pure 3- and 3,3-Disubstituted Pyrrolidines

  摘要：

  Enantiomerically pure bicyclic lactam 1, derived from (S)-phenylglycinol, underwent diastereoselective mono- and dialkylation affording substituted lactams 2 and 3 bearing tertiary and quaternary stereocenters. Reduction with LiAlH4 furnished N-(2'-hydroxy-1'-phenylethyl) pyrrolidines 4 which were efficiently debenzylated by catalytic hydrogenolysis to afford enantiomerically pure 3-mono- and 3,3-disubstituted pyrrolidines 5.

  DOI：

  10.1016/s0040-4039(00)79942-4

文献信息

• A Synthesis of Enantiomerically Pure 3- and 3,3-Disubstituted Pyrrolidines
  作者：Larry J. Westrum、A.I. Meyers

  DOI：10.1016/s0040-4039(00)79942-4

  日期：1994.2

  Enantiomerically pure bicyclic lactam 1, derived from (S)-phenylglycinol, underwent diastereoselective mono- and dialkylation affording substituted lactams 2 and 3 bearing tertiary and quaternary stereocenters. Reduction with LiAlH4 furnished N-(2'-hydroxy-1'-phenylethyl) pyrrolidines 4 which were efficiently debenzylated by catalytic hydrogenolysis to afford enantiomerically pure 3-mono- and 3,3-disubstituted pyrrolidines 5.