2-Bromomethyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propenone | 192582-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-Bromomethyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propenone
• CAS: 192582-81-3
• 化学式: C₁₄H₂₀BrNO₃S
• 分子量: 362.288
• InChiKey: UTTIFCLXMQDXKN-MJVIPROJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Bromomethyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propenone 在 silver-graphite 、 苯甲醛 、 锌 作用下， 以 四氢呋喃 为溶剂， 以13%的产率得到1,6-Bis-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,5-dimethylene-hexane-1,6-dione
  参考文献：
  名称：

  Enantioselective Dreiding-Schmidt reactions: asymmetric synthesis and analysis of α-methylene-γ-butyrolactones

  摘要：

  The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted alpha-methylene-gamma-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00166-3
• 作为产物：
  描述：

  2-(溴甲基)丙烯酸 、 sodium salt of (2S)-bornane-2,10-sultam 在 草酰氯 作用下， 生成 2-Chloromethyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propenone 、 2-Bromomethyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propenone 、 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-ylmethyl)-propenone
  参考文献：
  名称：

  Enantioselective Dreiding-Schmidt reactions: asymmetric synthesis and analysis of α-methylene-γ-butyrolactones

  摘要：

  The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted alpha-methylene-gamma-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00166-3