(4S)-3-[(2S)-7-bromo-2-methylheptanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one | 862828-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-[(2S)-7-bromo-2-methylheptanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
• 英文别名: (3(2S),4S)-3-(2-methyl-6-bromo-1-oxoheptyl)-4-(phenylmethyl)-2-oxazolidinone；3(2S),(4S)-3-(2-methyl-7-bromo-1-oxoheptyl)-4-(phenylmethyl)-2-oxazolidinone；(4S)-4-benzyl-3-[(2S)-7-bromo-2-methylheptanoyl]-1,3-oxazolidin-2-one
• CAS: 862828-10-2
• 化学式: C₁₈H₂₄BrNO₃
• 分子量: 382.297
• InChiKey: URMOHYRVBRNXNN-HOCLYGCPSA-N

物化性质

• 沸点：
  502.4±33.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(2S)-7-bromo-2-methylheptanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以97%的产率得到7-叠氮庚酸
  参考文献：
  名称：

  Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides

  摘要：

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.056
• 作为产物：
  描述：

  7-溴庚酸 在 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (4S)-3-[(2S)-7-bromo-2-methylheptanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  ω-溴-2(S)-甲基酸的不对称合成作为新型精氨酸、赖氨酸和巯基残留的前体

  摘要：

  摘要 已经合成了一系列 ω-溴-2(S)-甲基酸作为新型精氨酸 (Arg)、赖氨酸 (Lys) 和巯基类似物的前体。这些中间体含有 α-甲基，当掺入药物相关的肽中时，它们旨在掩盖 N 端胺。

  DOI：

  10.1081/scc-200061668

文献信息

• Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides
  作者：Kevin S. Orwig、Thomas A. Dix

  DOI：10.1016/j.tetlet.2005.08.056

  日期：2005.10

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of ω‐Bromo‐2(S)‐Methyl Acids as Precursors for Novel Arginine, Lysine, and Mercapto Residues
  作者：M. Kyle Hadden、Kyle P. Kokko、Thomas A. Dix

  DOI：10.1081/scc-200061668

  日期：2005.6.1

  Abstract A series of ω‐bromo‐2(S)‐methyl acids has been synthesized as precursors of novel arginine (Arg), lysine (Lys), and mercapto analogues. These intermediates contain α‐methyl groups and are designed to mask the N‐terminal amine when incorporated in pharmaceutically relevant peptides.

  摘要 已经合成了一系列 ω-溴-2(S)-甲基酸作为新型精氨酸 (Arg)、赖氨酸 (Lys) 和巯基类似物的前体。这些中间体含有 α-甲基，当掺入药物相关的肽中时，它们旨在掩盖 N 端胺。