(+/-)-α-n-hexyl-β-aminopropionic acid | 131932-63-3

• 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: (+/-)-α-n-hexyl-β-aminopropionic acid
• 英文别名: 2-(Aminomethyl)octanoic acid
• CAS: 131932-63-3
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: UZSGMMGZWXQCSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  trans-1-benzoyl-2-tert-butyl-5-n-hexyl-3-methylperhydropyrimidin-4-one 在 盐酸 作用下， 反应 8.0h， 以62%的产率得到(+/-)-α-n-hexyl-β-aminopropionic acid
  参考文献：
  名称：

  Asymmetric synthesis of .beta.-amino acids. 1. Highly diastereoselective addition of a racemic .beta.-alanine enolate derivative to electrophiles

  摘要：

  beta-Alanine, an inexpensive alpha-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group. The hydrolysis of the resulting adducts proceeds with 6 N hydrochloric acid to afford alpha-substituted beta-amino acids in good yields. These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure alpha-substituted beta-amino acids.

  DOI：

  10.1021/jo00007a053

文献信息

• RADIOLABELED PDE10 INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2435048B1

  公开（公告）日：2019-07-03
• JUARISTI, EUSEBIO;QUINTANA, DELIA;LAMATSCH, BERND;SEEBACH, DIETER, J. ORG. CHEM., 56,(1991) N, C. 2553-2557
  作者：JUARISTI, EUSEBIO、QUINTANA, DELIA、LAMATSCH, BERND、SEEBACH, DIETER

  DOI：——

  日期：——
• Asymmetric synthesis of .beta.-amino acids. 1. Highly diastereoselective addition of a racemic .beta.-alanine enolate derivative to electrophiles
  作者：Eusebio Juaristi、Delia Quintana、Bernd Lamatsch、Dieter Seebach

  DOI：10.1021/jo00007a053

  日期：1991.3

  beta-Alanine, an inexpensive alpha-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group. The hydrolysis of the resulting adducts proceeds with 6 N hydrochloric acid to afford alpha-substituted beta-amino acids in good yields. These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure alpha-substituted beta-amino acids.