tert-butyl N-[(3S)-1-[methoxy(methyl)amino]-5-methyl-1-oxohexan-3-yl]carbamate | 200949-36-6

• 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: tert-butyl N-[(3S)-1-[methoxy(methyl)amino]-5-methyl-1-oxohexan-3-yl]carbamate
• CAS: 200949-36-6
• 化学式: C₁₄H₂₈N₂O₄
• 分子量: 288.387
• InChiKey: QFPSWFHGPIGKNX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(3S)-1-[methoxy(methyl)amino]-5-methyl-1-oxohexan-3-yl]carbamate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以70%的产率得到tert-butyl (S)-(5-methyl-1-oxohexan-3-yl)carbamate
  参考文献：
  名称：

  Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part

  摘要：

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).

  DOI：

  10.1016/s0223-5234(99)80063-4
• 作为产物：
  描述：

  Boc-Leu-O-COO-isoBu 在 silver benzoate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 tert-butyl N-[(3S)-1-[methoxy(methyl)amino]-5-methyl-1-oxohexan-3-yl]carbamate
  参考文献：
  名称：

  Direct synthesis of N-protected β-amino dimethylhydroxamates: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate Ψ[CH2CH2NH]

  摘要：

  A rapid and efficient one-step synthesis of N-protected beta-amino dimethylhydroxamates starting from diazo ketones is reported A Fmoc-protected beta-amino aldehyde obtained by reduction of its corresponding dimethylhydroxamate was incorporated during solid phase assembly of an antigenic peptide. The resulting pseudopeptide containing an ethylene amino bond Psi[CH2CH2NH] was efficiently recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00675-3

文献信息

• Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines
  作者：Nicolas Gouault、Myriam Le Roch、Adèle Cheignon、Philippe Uriac、Michèle David

  DOI：10.1021/ol201698m

  日期：2011.8.19

  The enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy are reported. Excellent stereocontrol was observed during the cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.
• Direct synthesis of N-protected β-amino dimethylhydroxamates: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate Ψ[CH2CH2NH]
  作者：David Limal、Anne Quesnel、Jean-Paul Briand

  DOI：10.1016/s0040-4039(98)00675-3

  日期：1998.6

  A rapid and efficient one-step synthesis of N-protected beta-amino dimethylhydroxamates starting from diazo ketones is reported A Fmoc-protected beta-amino aldehyde obtained by reduction of its corresponding dimethylhydroxamate was incorporated during solid phase assembly of an antigenic peptide. The resulting pseudopeptide containing an ethylene amino bond Psi[CH2CH2NH] was efficiently recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part
  作者：M Llinares、C Devin、J Azay、G Bergé、JA Fehrentz、J Martinez

  DOI：10.1016/s0223-5234(99)80063-4

  日期：1997.10

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).