(S)-3-benzamido-3-(4-chlorophenyl)propanoic acid | 1245770-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-benzamido-3-(4-chlorophenyl)propanoic acid
• 英文别名: (3S)-3-benzamido-3-(4-chlorophenyl)propanoic acid
• CAS: 1245770-64-2
• 化学式: C₁₆H₁₄ClNO₃
• 分子量: 303.745
• InChiKey: KRVKSWSTGNFTME-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-N-[1-(4-chlorophenyl)but-3-enyl]benzamide 在 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以99%的产率得到(S)-3-benzamido-3-(4-chlorophenyl)propanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

  摘要：

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.046

文献信息

• Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
  作者：Raquel Almansa、Juan F. Collados、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2010.03.046

  日期：2010.6

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.