(S)-8-ethoxycarbonyl-2-methyl-3-methylene-1-oxa-8-azaspiro<4,5>decane | 144282-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (S)-8-ethoxycarbonyl-2-methyl-3-methylene-1-oxa-8-azaspiro<4,5>decane
• 英文别名: ethyl (2S)-2-methyl-3-methylidene-1-oxa-8-azaspiro[4.5]decane-8-carboxylate
• CAS: 144282-57-5
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: CLDDNIKTHFKFGH-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• 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)-8-ethoxycarbonyl-2-methyl-3-methylene-1-oxa-8-azaspiro<4,5>decane 在 红铝 作用下， 以 甲苯 为溶剂， 以64%的产率得到YM796
  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：

  ethyl 4-methylenepiperidine-1-carboxylate 在 sodium hydroxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 silica gel 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 (S)-8-ethoxycarbonyl-2-methyl-3-methylene-1-oxa-8-azaspiro<4,5>decane
  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

文献信息

• An Efficient Synthesis of (S)-(-)-2,8-Dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane by Cobaloxime(I)-mediated Radical Cyclization
  作者：Shin-ichi Tsukamoto、Yutaka Kondo、Susumu Igarashi

  DOI：10.3987/com-95-7113

  日期：——

  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.