ethyl (5S)-4-oxo-6-phenyl-5-(phenylmethoxycarbonylamino)hexanoate | 143601-46-1

• 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: ethyl (5S)-4-oxo-6-phenyl-5-(phenylmethoxycarbonylamino)hexanoate
• CAS: 143601-46-1
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: RHXGQGWDFVIPHH-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (5S)-4-oxo-6-phenyl-5-(phenylmethoxycarbonylamino)hexanoate 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 生成 phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate 、 phenylmethyl [(1S)-2-phenyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate
  参考文献：
  名称：

  A simple synthetic approach to Cbz-Phe-Ψ-(Ch2)-Gly-Pro-OMe and related Peptide Isosteres

  摘要：

  A new approach to ketomethylene and hydroxymethylene peptide isosteres has been developed which is simple, direct, and highly convergent. A key feature is construction of the central bond of a gamma-keto ester by alkylation of a t-butyl beta-keto ester with an alpha-bromo ester.

  DOI：

  10.1016/s0040-4039(00)92507-3
• 作为产物：
  描述：

  (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-5-phenylpentanoate 在 sodium hydride 、 三氟乙酸 作用下， 生成 ethyl (5S)-4-oxo-6-phenyl-5-(phenylmethoxycarbonylamino)hexanoate
  参考文献：
  名称：

  A simple synthetic approach to Cbz-Phe-Ψ-(Ch2)-Gly-Pro-OMe and related Peptide Isosteres

  摘要：

  A new approach to ketomethylene and hydroxymethylene peptide isosteres has been developed which is simple, direct, and highly convergent. A key feature is construction of the central bond of a gamma-keto ester by alkylation of a t-butyl beta-keto ester with an alpha-bromo ester.

  DOI：

  10.1016/s0040-4039(00)92507-3

文献信息

• New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds
  作者：Maddalena Alongi、Giacomo Minetto、Maurizio Taddei

  DOI：10.1016/j.tetlet.2005.07.155

  日期：2005.10

  pyrrole-based amino acids have been prepared through the microwave assisted Paal–Knorr reaction of 1–4 ketoesters derived from the corresponding β-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions 1 or 2. These compounds were used to prepare constrained oligopeptides

  通过微波辅助Paal-Knorr反应衍生自具有功能同源性的相应β-酮酸酯的1-4个酮酸酯，已经制备了一个新的基于吡咯的氨基酸家族。羧基位于吡咯的3位，而受Cbz部分保护的氨基位于1或2位的侧链上。这些化合物用于制备受限的寡肽。