(S)-2-[2-(5-Fluoro-2,4-dinitro-phenylamino)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester | 717139-76-9

• 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-[2-(5-Fluoro-2,4-dinitro-phenylamino)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-[[2-(5-fluoro-2,4-dinitroanilino)acetyl]amino]-3-(4-hydroxyphenyl)propanoate
• CAS: 717139-76-9
• 化学式: C₁₈H₁₇FN₄O₈
• 分子量: 436.353
• InChiKey: PVGXVRUTOZVSTB-AWEZNQCLSA-N

物化性质

• 沸点：
  722.4±60.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-[2-(5-Fluoro-2,4-dinitro-phenylamino)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以38%的产率得到(S)-4,6-Dinitro-10-oxo-2-oxa-8,11-diaza-tricyclo[12.2.2.1^3,7]nonadeca-1(17),3,5,7(19),14(18),15-hexaene-12-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of a novel 14-membered highly constrained cyclic peptidic scaffold

  摘要：

  The synthesis and NMR analysis of a novel highly constrained scaffold is described. The 14-membered macrocyclic ring structure was inspired by many medicinally relevant natural products that also contain the bi-aryl ether moiety. The synthesis required only commercially available starting materials and involved a base mediated SNAr cyclization. A conformational search,,vas performed, which indicated a strong preference for a single conformation, which was consistent with observed ROE signals by NMR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.131
• 作为产物：
  描述：

  methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride 在 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.5h， 生成 (S)-2-[2-(5-Fluoro-2,4-dinitro-phenylamino)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of a novel 14-membered highly constrained cyclic peptidic scaffold

  摘要：

  The synthesis and NMR analysis of a novel highly constrained scaffold is described. The 14-membered macrocyclic ring structure was inspired by many medicinally relevant natural products that also contain the bi-aryl ether moiety. The synthesis required only commercially available starting materials and involved a base mediated SNAr cyclization. A conformational search,,vas performed, which indicated a strong preference for a single conformation, which was consistent with observed ROE signals by NMR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.131

文献信息

• Synthesis of a novel 14-membered highly constrained cyclic peptidic scaffold
  作者：Christopher J. Arnusch、Roland J. Pieters

  DOI：10.1016/j.tetlet.2004.03.131

  日期：2004.5

  The synthesis and NMR analysis of a novel highly constrained scaffold is described. The 14-membered macrocyclic ring structure was inspired by many medicinally relevant natural products that also contain the bi-aryl ether moiety. The synthesis required only commercially available starting materials and involved a base mediated SNAr cyclization. A conformational search,,vas performed, which indicated a strong preference for a single conformation, which was consistent with observed ROE signals by NMR. (C) 2004 Elsevier Ltd. All rights reserved.