(4R,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-5-methyl-2-methylenehexanoate | 1211540-49-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-5-methyl-2-methylenehexanoate
• 英文别名: ethyl (4R)-4-[[(R)-tert-butylsulfinyl]amino]-5-methyl-2-methylidenehexanoate
• CAS: 1211540-49-6
• 化学式: C₁₄H₂₇NO₃S
• 分子量: 289.439
• InChiKey: DDMYTTNUALKYKN-CWTRNNRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-N-(tert-butanesulfinyl)-N-(2-methylpropyliden)amine 、 2-溴甲基丙烯酸乙酯 在 indium 、 sodium bromide 作用下， 以 水 为溶剂， 反应 48.0h， 以73%的产率得到(4S,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-5-methyl-2-methylenehexanoate
  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

• Enantioselective Synthesis of α-Methylene-γ-butyrolactams Using N-tert-Butanesulfinamides
  作者：Miguel Yus、Francisco Foubelo、Haythem K. Dema

  DOI：10.3987/com-10-s(e)94

  日期：——

  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.