[(S)-2-(Methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester | 188689-84-1

• 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-(Methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester
• CAS: 188689-84-1
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: IZKUECOOOCOOFN-NSHDSACASA-N

物化性质

• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)-2-(Methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (E)-(S)-5-Benzyloxycarbonylamino-hex-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  Peptide based inhibitors of interleukin-8: structural simplification and enhanced potency

  摘要：

  Important areas of a lead peptide inhibitor of IL-I had been previously identified. Chemical modification led to the identification of key amide bonds which allowed the replacement of the central section of the peptide with modified amino acids and spacers. This approach led to inhibitors of lower molecular weight and of increased potency. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00036-x
• 作为产物：
  描述：

  (S)-3-Cbz-氨基丁酸 、 二甲羟胺盐酸盐 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到[(S)-2-(Methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Peptide based inhibitors of interleukin-8: structural simplification and enhanced potency

  摘要：

  Important areas of a lead peptide inhibitor of IL-I had been previously identified. Chemical modification led to the identification of key amide bonds which allowed the replacement of the central section of the peptide with modified amino acids and spacers. This approach led to inhibitors of lower molecular weight and of increased potency. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00036-x

文献信息

• Synthesis of 2,6-Disubstituted Piperidine-Bearing α-Amino Acid Side-Chains
  作者：Damien Boeglin、Annie Heitz、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1002/ejoc.200300148

  日期：2003.8

  A straightforward synthesis of 2,6-disubstituted piperidines bearing α-amino acid side-chains was developed. Synthesis was based on a Horner−Wadsworth−Emmons condensation of a β-ketophosphonate derived from an α-amino acid residue with a β-homologated aldehyde of an N-protected amino acid residue. The generated α-β unsaturated ketones were then reduced, deprotected, and cyclized in a hydrogenation/hydrogenolysis

  开发了带有 α-氨基酸侧链的 2,6-二取代哌啶的直接合成。合成基于衍生自α-氨基酸残基的β-酮膦酸酯与N-保护氨基酸残基的β-同源醛的Horner-Wadsworth-Emmons缩合。然后将生成的 α-β 不饱和酮还原、脱保护并在氢化/氢解一锅法中环化以产生哌啶部分。在获得的分子中引入新的构象限制允许通过 NMR 实验完全分配立体中心。这项分配使我们能够在环化过程中提出一条机械途径，解释环外碳中心构型的丢失。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization
  作者：Nicolas Gouault、Myriam Le Roch、Gisele de Campos Pinto、Michèle David

  DOI：10.1039/c2ob25685a

  日期：——

  A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural products in few steps and good overall yields.

  我们开发了一种以 D-丙氨酸为原料全合成哌啶生物碱 (+)-241D、异橙皮苷和异橙皮苷 A 的新方法。获得手性吡啶酮中间体的关键步骤是通过金介导的环化反应实现的。最后，在不同的还原条件下，只需几步就能得到这些天然产物，而且总收率很高。