(3S,4S)-3,4-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid | 137959-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (3S,4S)-3,4-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• 英文别名: (3S,4S)-3,4-dimethyl-2,4-dihydro-1H-isoquinoline-3-carboxylic acid
• CAS: 137959-86-5
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: RDDHASYTWDDFCO-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,5S,5αS)-1-Benzoyl-2-tert-butyl-3,5-dimethyl-5-(α-methylbenzyl)imidazolidin-4-one 在 盐酸 作用下， 反应 15.0h， 生成 (3S,4S)-3,4-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity

  摘要：

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.

  DOI：

  10.1021/jo00086a033

文献信息

• Asymmetric synthesis of topographically constrained amino acids: synthesis of the optically pure isomers of α,β-dimethyl-phenylalanine and α,β-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
  作者：Wieslaw M. Kazmierski、Victor J. Hruby

  DOI：10.1016/s0040-4039(00)93551-2

  日期：1991.10

  All four isomers of α,β-dimethylphenylalanine and α,β-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid have been synthesized in high optical purity for use in the design of topographically constrained peptides.

  已经以高光学纯度合成了α，β-二甲基苯丙氨酸和α，β-二甲基-1,2,3,4-四氢异喹啉-3-羧酸的所有四个异构体，用于设计受地形约束的肽。
• New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity
  作者：Wieslaw M. Kazmierski、Zofia Urbanczyk-Lipkowska、Victor J. Hruby

  DOI：10.1021/jo00086a033

  日期：1994.4

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.