(4R,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-2-methylene-4-phenylbutanoate | 1211540-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-2-methylene-4-phenylbutanoate
• CAS: 1211540-51-0
• 化学式: C₁₇H₂₅NO₃S
• 分子量: 323.456
• InChiKey: YQQOBSCWQYQBGI-IVZQSRNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-2-methylene-4-phenylbutanoate 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.5h， 以93%的产率得到(-)-(R)-3-methylene-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  One-Pot Synthesis of Chiral α-Methylene-γ-lactams with Excellent Diastereoselectivities and Enantioselectivities

  摘要：

  An efficient one-pot asymmetric synthesis of highly substituted gamma-lactams containing a-methylene groups has been successfully developed. A wide range of gamma-lactams could be obtained in high yields with excellent diastereomeric ratios of up to 99:1 in favor of trans isomers. In particular, excellent enantioselectivities of the two newly formed stereogenic centers with up to 99% ee were observed.

  DOI：

  10.1021/ol102148b
• 作为产物：
  描述：

  (R)-N-benzylidene-2-methylpropane-2-sulfinamide 、 2-溴甲基丙烯酸乙酯 在 lithium chloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以94%的产率得到(4R,R(S))-ethyl N-(tert-butylsulfinyl)-4-amino-2-methylene-4-phenylbutanoate
  参考文献：
  名称：

  One-Pot Synthesis of Chiral α-Methylene-γ-lactams with Excellent Diastereoselectivities and Enantioselectivities

  摘要：

  An efficient one-pot asymmetric synthesis of highly substituted gamma-lactams containing a-methylene groups has been successfully developed. A wide range of gamma-lactams could be obtained in high yields with excellent diastereomeric ratios of up to 99:1 in favor of trans isomers. In particular, excellent enantioselectivities of the two newly formed stereogenic centers with up to 99% ee were observed.

  DOI：

  10.1021/ol102148b

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.