(S)-3-methylene-5-octylpyrrolidin-2-one | 1211540-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-3-methylene-5-octylpyrrolidin-2-one
• 英文别名: (5S)-3-methylidene-5-octylpyrrolidin-2-one
• CAS: 1211540-37-2
• 化学式: C₁₃H₂₃NO
• 分子量: 209.332
• InChiKey: LCKRTCVHIKZOFE-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-[tert-butyl-(S)-sulfinyl]-nonaldimine 在 盐酸 、 indium 、 sodium bromide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 51.0h， 生成 (S)-3-methylene-5-octylpyrrolidin-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of α-Methylene-γ-butyrolactams Using N-tert-Butanesulfinamides

  摘要：

  Indium-mediated coupling of ethyl 2-(bromomethyl)acrylate (1) and chiral N-tert-butanelsulfinylimines 2 in a saturated sodium bromide aqueous solution leads to N-tert-butanesulfinyl aminoesters 3 in high yields and diastereoselectivities. After column chromatography purification, enantiomerically pure aminoesters 3 were converted into the expected alpha-methylene-gamma-butyrolactams 4 in a one-pot process.

  DOI：

  10.3987/com-10-s(e)94

文献信息

• Stereoselective Synthesis of α-Methylene-γ-butyrolactams from Ethyl 2-(Bromomethyl)acrylate and Chiral Sulfinyl Aldimines Mediated by Indium
  作者：Miguel Yus、Francisco Foubelo、Haythem K. Dema

  DOI：10.3987/com-09-s(s)27

  日期：——

  The reaction of ethyl 2-(bromomethyl)acrylate (1) with chiral N-tert-butylsulfinyl aldimines 2 and indium powder in THF at 100 degrees C for 48 h affords, after hydrolysis, a mixture of N-tert-butylsulfinyl aminoesters 3 and alpha-methylene-gamma-butyrolactams 4. From the reaction mixture, compounds 3 were quantitatively converted to the expected butyrolactams 4 after removal of the tert-butylsulfinyl group under acidic conditions and final basic workup. The whole process takes place in high overall yields and with fairly good stereoselectivities.