(3S,8aR)-8a-methyl-3-phenyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile | 258286-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3S,8aR)-8a-methyl-3-phenyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS: 258286-06-5
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: QLVBFVWBXSYGIL-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,8aR)-8a-methyl-3-phenyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile 在 六甲基磷酰三胺 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 氨 、 calcium 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,6R)-4-butyl-6-methylpiperidin-2-one
  参考文献：
  名称：

  Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines: extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles

  摘要：

  Enantiomerically pure cis-2,4-disubstituted piperidines were synthesized from chiral thiolactam 2 in six steps via a highly diastereoselective homoenolate alkylation which set the stereochemistry at the C4 carbon. In addition, two cleavage methods were used to cleave the lactam to the desired piperidines with a high level of diastereoselection at the newly created C2 stereocenter. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01784-0
• 作为产物：
  描述：

  氰化钾 、 (3S,8aR)-8a-methyl-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-thione 在 triethyloxonium fluoroborate 、 copper(l) iodide 、 碘 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(3S,8aR)-8a-methyl-3-phenyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines: extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles

  摘要：

  Enantiomerically pure cis-2,4-disubstituted piperidines were synthesized from chiral thiolactam 2 in six steps via a highly diastereoselective homoenolate alkylation which set the stereochemistry at the C4 carbon. In addition, two cleavage methods were used to cleave the lactam to the desired piperidines with a high level of diastereoselection at the newly created C2 stereocenter. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01784-0

文献信息

• Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines: extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles
  作者：Michael P. Dwyer、Jason E. Lamar、A.I. Meyers

  DOI：10.1016/s0040-4039(99)01784-0

  日期：1999.12

  Enantiomerically pure cis-2,4-disubstituted piperidines were synthesized from chiral thiolactam 2 in six steps via a highly diastereoselective homoenolate alkylation which set the stereochemistry at the C4 carbon. In addition, two cleavage methods were used to cleave the lactam to the desired piperidines with a high level of diastereoselection at the newly created C2 stereocenter. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.