(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide | 1287731-48-9

• 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: (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide
• 英文别名: (3R)-N-methoxy-N-methyl-3-[(4-methylphenyl)sulfonylamino]-3-phenylpropanamide
• CAS: 1287731-48-9
• 化学式: C₁₈H₂₂N₂O₄S
• 分子量: 362.45
• InChiKey: IPODUFKHAMEIKG-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide 在 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 (2S,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenyl-1-butylpropanone
  参考文献：
  名称：

  Asymmetric Synthesis of anti-α-Substituted β-Amino Ketones from Sulfinimines

  摘要：

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.

  DOI：

  10.1021/jo2002352
• 作为产物：
  描述：

  (S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 8.0h， 以86%的产率得到(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide
  参考文献：
  名称：

  Asymmetric Synthesis of anti-α-Substituted β-Amino Ketones from Sulfinimines

  摘要：

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.

  DOI：

  10.1021/jo2002352

文献信息

• Asymmetric Synthesis of <i>anti</i>-α-Substituted β-Amino Ketones from Sulfinimines
  作者：Franklin A. Davis、Peng Xu

  DOI：10.1021/jo2002352

  日期：2011.5.6

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.