(S)-4-bromomethyl-1-ethoxycarbonyl-4-<(1-methyl-2-propynyl)oxy>piperidine | 144282-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-4-bromomethyl-1-ethoxycarbonyl-4-<(1-methyl-2-propynyl)oxy>piperidine
• 英文别名: ethyl 4-(bromomethyl)-4-[(2S)-but-3-yn-2-yl]oxypiperidine-1-carboxylate
• CAS: 144282-56-4
• 化学式: C₁₃H₂₀BrNO₃
• 分子量: 318.211
• InChiKey: OPAAJXRSTVBWPR-NSHDSACASA-N

物化性质

• 沸点：
  386.8±32.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-bromomethyl-1-ethoxycarbonyl-4-<(1-methyl-2-propynyl)oxy>piperidine 在 亚磷酸三苯酯 、 sodium hydroxide 、 sodium tetrahydroborate 、 臭氧 、 红铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 21.0h， 生成 (S)-2,8-Dimethyl-1-oxa-8-aza-spiro[4.5]decan-3-one
  参考文献：
  名称：

  An Efficient Synthesis of (S)-(-)-2,8-Dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane by Cobaloxime(I)-mediated Radical Cyclization

  摘要：

  Optically pure (S)-(-)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]-decane (1) was synthesized by alkoxybromination of 1-ethoxycarbonyl-4-methylenepiperidine (4) with (S)-3-butyn-2-ol and N-bromosuccinimide followed by radical cyclization mediated by cobaloxime(I) in 15% overall yield. Reaction conditions for the alkoxybromination reaction were devised to reduce the requirement of the optically pure alcohol.

  DOI：

  10.3987/com-95-7113
• 作为产物：
  描述：

  (S)-(-)-3-丁炔-2-醇 、 ethyl 4-methylenepiperidine-1-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 silica gel 作用下， 反应 8.0h， 生成 (S)-4-bromomethyl-1-ethoxycarbonyl-4-<(1-methyl-2-propynyl)oxy>piperidine
  参考文献：
  名称：

  An Efficient Synthesis of (S)-(-)-2,8-Dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane by Cobaloxime(I)-mediated Radical Cyclization

  摘要：

  Optically pure (S)-(-)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]-decane (1) was synthesized by alkoxybromination of 1-ethoxycarbonyl-4-methylenepiperidine (4) with (S)-3-butyn-2-ol and N-bromosuccinimide followed by radical cyclization mediated by cobaloxime(I) in 15% overall yield. Reaction conditions for the alkoxybromination reaction were devised to reduce the requirement of the optically pure alcohol.

  DOI：

  10.3987/com-95-7113