(3R,5S,8aR)-8-bromo-3-phenyl-3,5,6,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile | 226923-12-2

• 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: (3R,5S,8aR)-8-bromo-3-phenyl-3,5,6,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS: 226923-12-2
• 化学式: C₁₄H₁₃BrN₂O
• 分子量: 305.174
• InChiKey: UMBNLUDCEJBTHD-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (3R,5S,8aR)-8-bromo-3-phenyl-3,5,6,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile 在 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of polyfunctionalized piperidines: substitution at the C-4 position

  摘要：

  The electrochemical bis-bromination of the chiral building block 1 followed by a dehydrobromination step allowed the preparation of a bromopiperideine 3. The stereoselective addition of nucleophiles onto this key intermediate permitted the synthesis of various 4-substituted piperidine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00625-5
• 作为产物：
  描述：

  (3R,5S,8aR)-8,8-dibromo-3-phenyl-2,3,5,6,7,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(3R,5S,8aR)-8-bromo-3-phenyl-3,5,6,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
  参考文献：
  名称：

  Asymmetric synthesis of polyfunctionalized piperidines: substitution at the C-4 position

  摘要：

  The electrochemical bis-bromination of the chiral building block 1 followed by a dehydrobromination step allowed the preparation of a bromopiperideine 3. The stereoselective addition of nucleophiles onto this key intermediate permitted the synthesis of various 4-substituted piperidine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00625-5

文献信息

• Asymmetric synthesis of polyfunctionalized piperidines: substitution at the C-4 position
  作者：Florence Billon-Souquet、Thierry Martens、Jacques Royer

  DOI：10.1016/s0040-4039(99)00625-5

  日期：1999.5

  The electrochemical bis-bromination of the chiral building block 1 followed by a dehydrobromination step allowed the preparation of a bromopiperideine 3. The stereoselective addition of nucleophiles onto this key intermediate permitted the synthesis of various 4-substituted piperidine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.