(S)-2-(3'-phenylpropyl)alanine | 136707-24-9

• 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)-2-(3'-phenylpropyl)alanine
• 英文别名: (2S)-2-amino-2-methyl-5-phenylpentanoic acid
• CAS: 136707-24-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: MVAJOGCZNRWTRF-LBPRGKRZSA-N

物化性质

• 沸点：
  378.9±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  Cinnamyl bromide 在 palladium dichloride 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0 ℃ 、344.73 kPa 条件下， 反应 37.5h， 生成 (S)-2-(3'-phenylpropyl)alanine
  参考文献：
  名称：

  Asymmetric synthesis of monosubstituted and .alpha.,.alpha.-disubstituted .alpha.-amino acids via diastereoselective glycine enolate alkylations

  摘要：

  The enolates derived from the optically active (5S,6R)- and (5R,6S)-4(tert-butyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (1a,b) and (5S,6R)- and (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (2a,b) efficiently couple with alkyl halides to afford the corresponding anti-alpha-monosubstituted oxazinones (3 and 4). The enolate alkylation of the alpha-monosubstituted oxazinones (3 and 4) provides the corresponding alpha,alpha-disubstituted oxazinones (7 and 8). Dissolving-metal reduction of the homologated oxazinones allows the direct preparation of t-BOC-protected alpha-amino acids. In the case of a dissolving-metal-reducible functionality, hydrogenation over a Pd0 catalyst furnishes the zwitterionic amino acids. By employing this protocol several amino acids or their corresponding N-t-BOC derivatives, such as allylglycine, alanine, phenylalanine, beta-ethylaspartic acid, alpha-methylphenylalanine, N-(tert-butyloxycarbonyl)dimethallylglycine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)norvaline, N-(tert-butyloxycarbonyl)-2-(3'-methyl-2'-butenyl)alanine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)alanine, 2-(3'-phenylpropyl)alanine, 2-amino-6-(acetyloxy)hexanoic acid, and 2(tert-butyloxycarbonyl)amino-6-[(p-methoxybenzyl)thio]hexanoic acid, are prepared in high enantiomeric excess.

  DOI：

  10.1021/ja00024a038

文献信息

• Asymmetric synthesis of monosubstituted and .alpha.,.alpha.-disubstituted .alpha.-amino acids via diastereoselective glycine enolate alkylations
  作者：Robert M. Williams、Myeong Nyeo Im

  DOI：10.1021/ja00024a038

  日期：1991.11

  The enolates derived from the optically active (5S,6R)- and (5R,6S)-4(tert-butyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (1a,b) and (5S,6R)- and (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (2a,b) efficiently couple with alkyl halides to afford the corresponding anti-alpha-monosubstituted oxazinones (3 and 4). The enolate alkylation of the alpha-monosubstituted oxazinones (3 and 4) provides the corresponding alpha,alpha-disubstituted oxazinones (7 and 8). Dissolving-metal reduction of the homologated oxazinones allows the direct preparation of t-BOC-protected alpha-amino acids. In the case of a dissolving-metal-reducible functionality, hydrogenation over a Pd0 catalyst furnishes the zwitterionic amino acids. By employing this protocol several amino acids or their corresponding N-t-BOC derivatives, such as allylglycine, alanine, phenylalanine, beta-ethylaspartic acid, alpha-methylphenylalanine, N-(tert-butyloxycarbonyl)dimethallylglycine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)norvaline, N-(tert-butyloxycarbonyl)-2-(3'-methyl-2'-butenyl)alanine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)alanine, 2-(3'-phenylpropyl)alanine, 2-amino-6-(acetyloxy)hexanoic acid, and 2(tert-butyloxycarbonyl)amino-6-[(p-methoxybenzyl)thio]hexanoic acid, are prepared in high enantiomeric excess.