(S)-2-Amino-2-(2,2-dimethoxy-ethyl)-3-methyl-butyric acid methyl ester | 312912-96-2

• 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: (S)-2-Amino-2-(2,2-dimethoxy-ethyl)-3-methyl-butyric acid methyl ester
• 英文别名: methyl (2S)-2-amino-4,4-dimethoxy-2-propan-2-ylbutanoate
• CAS: 312912-96-2
• 化学式: C₁₀H₂₁NO₄
• 分子量: 219.281
• InChiKey: DIPISBYATZUWJV-JTQLQIEISA-N

物化性质

• 沸点：
  279.5±40.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-2-(2,2-dimethoxy-ethyl)-3-methyl-butyric acid methyl ester 在 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 甲苯 、 苯 为溶剂， 反应 5.25h， 生成 ((S)-4-Benzyl-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl)-acetaldehyde
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  (S)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester 在 palladium on activated charcoal 对甲苯磺酸 、 环己烯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 (S)-2-Amino-2-(2,2-dimethoxy-ethyl)-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974

文献信息

• Design, Synthesis, and Solution Structure of a Pyrrolinone-Based β-Turn Peptidomimetic
  作者：Amos B. Smith、Wenyong Wang、Paul A. Sprengeler、Ralph Hirschmann

  DOI：10.1021/ja002964w

  日期：2000.11.1
• Design, Synthesis, and Structural Analysis of <scp>d</scp>,<scp>l</scp>-Mixed Polypyrrolinones. 1. From Nonpeptide Peptidomimetics to Nanotubes
  作者：Amos B. Smith, III、Wenyong Wang、Adam K. Charnley、Patrick J. Carroll、Craig S. Kenesky、Ralph Hirschmann

  DOI：10.1021/ol101007n

  日期：2010.7.2

  To expand the potential conformational space available to the polypyrroline structural motif, an open chain, D,L-alternating hexapyrrolinone was designed and synthesized. Structural studies, including solution NMR and X-ray crystallographic analysis, revealed that the hexapyrrolinone adopts a turn conformation both in solution and in the solid state, with aggregation in solution and a nanotube-like quaternary structure in the crystal.