(R)-2-benzamido-4-phenylbutanoic acid | 149832-20-2

• 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: (R)-2-benzamido-4-phenylbutanoic acid
• 英文别名: (2R)-2-benzamido-4-phenylbutanoic acid
• CAS: 149832-20-2
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: KYQLWMGRTKMDAA-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  N-[1-(2-phenylethyl)prop-2-enyl]benzamide 在 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 生成 (S)-2-benzoylamino-4-phenylbutyric acid 、 (R)-2-benzamido-4-phenylbutanoic 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

• Hexahydronaphth(1,2-b)-1,4-oxazines, process for their preparation and pharmaceutical formulation containing them
  申请人：Merck & Co., Inc.

  公开号：EP0080115A2

  公开（公告）日：1983-06-01

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display α2-adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamido- tetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘并[1,2-b]-1,4-噁嗪具有多巴胺能活性，并显示出α2-肾上腺素能受体拮抗作用。 它们可用于治疗帕金森病、抑郁症和高血压。 一种重要的制备方法是将适当的 2-氯乙酰胺基四氢萘-1-醇闭环，并还原由此产生的环状酰胺羰基。
• US4420480A
  申请人：——

  公开号：US4420480A

  公开（公告）日：1983-12-13
• 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.