2-(2-{Butyl-[2-(3-hydroxy-phenyl)-acetyl]-amino}-octanoylamino)-3-(4-fluoro-3-nitro-phenyl)-propionic acid ethyl ester | 389634-83-7

• 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: 2-(2-{Butyl-[2-(3-hydroxy-phenyl)-acetyl]-amino}-octanoylamino)-3-(4-fluoro-3-nitro-phenyl)-propionic acid ethyl ester
• 英文别名: Ethyl 2-[2-[butyl-[2-(3-hydroxyphenyl)acetyl]amino]octanoylamino]-3-(4-fluoro-3-nitrophenyl)propanoate；ethyl 2-[2-[butyl-[2-(3-hydroxyphenyl)acetyl]amino]octanoylamino]-3-(4-fluoro-3-nitrophenyl)propanoate
• CAS: 389634-83-7
• 化学式: C₃₁H₄₂FN₃O₇
• 分子量: 587.689
• InChiKey: SZKXHFZLGUAFMP-UHFFFAOYSA-N

物化性质

• 沸点：
  766.1±60.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2-{Butyl-[2-(3-hydroxy-phenyl)-acetyl]-amino}-octanoylamino)-3-(4-fluoro-3-nitro-phenyl)-propionic acid ethyl ester 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 10-Butyl-11-hexyl-19-methanesulfonylamino-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid ethyl ester
  参考文献：
  名称：

  A Rapid Access to Biaryl Ether Containing Macrocycles by Pairwise Use of Ugi 4CR and Intramolecular S_NAr-Based Cycloetherification

  摘要：

  [GRAPHICS]From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two operations by combination of the Ugi four-component reaction and an intramolecular: SNAr reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. A Ugi reaction promoted by ammonium chloride In aprotic solvent is documented for the first time.

  DOI：

  10.1021/ol0168420
• 作为产物：
  描述：

  4-氟-3-硝基苄醇 在 sodium hydroxide 、 三溴化磷 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 生成 2-(2-{Butyl-[2-(3-hydroxy-phenyl)-acetyl]-amino}-octanoylamino)-3-(4-fluoro-3-nitro-phenyl)-propionic acid ethyl ester
  参考文献：
  名称：

  A Rapid Access to Biaryl Ether Containing Macrocycles by Pairwise Use of Ugi 4CR and Intramolecular S_NAr-Based Cycloetherification

  摘要：

  [GRAPHICS]From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two operations by combination of the Ugi four-component reaction and an intramolecular: SNAr reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. A Ugi reaction promoted by ammonium chloride In aprotic solvent is documented for the first time.

  DOI：

  10.1021/ol0168420

文献信息

• Rapid and diverse route to natural product-like biaryl ether containing macrocycles
  作者：Pierre Cristau、Jean-Pierre Vors、Jieping Zhu

  DOI：10.1016/j.tet.2003.08.031

  日期：2003.9

  four-component reaction and an intramolecular nucleophilic aromatic substitution (SNAr) has been developed for the rapid access to biaryl-ether containing macrocycles. In the course of this study, we documented that ammonium chloride can promote the Ugi-4CR in non-polar aprotic solvent (toluene) without the interference of an alternative Passerini reaction. Solid phase synthesis of macrocycles by this two-step

  涉及的Ugi四组分反应和分子内的亲核芳香取代（S两步序列Ñ AR）已被开发为快速访问包含大环化合物的二芳基-醚。在本研究过程中，我们记录了氯化铵可在非极性非质子传递溶剂（甲苯）中促进Ugi-4CR，而不会受到其他Passerini反应的干扰。还使用聚合物（Wang树脂）负载的α-（4'-氟-3'-硝基）苯乙基异氰基乙酸酯作为输入之一，开发了通过此两步序列的大环化合物的固相合成。
• A Rapid Access to Biaryl Ether Containing Macrocycles by Pairwise Use of Ugi 4CR and Intramolecular S_NAr-Based Cycloetherification
  作者：Pierre Cristau、Jean-Pierre Vors、Jieping Zhu

  DOI：10.1021/ol0168420

  日期：2001.12.1

  [GRAPHICS]From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two operations by combination of the Ugi four-component reaction and an intramolecular: SNAr reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. A Ugi reaction promoted by ammonium chloride In aprotic solvent is documented for the first time.