methyl 2'-(2-bromoacetyl)-5-phenyl[2,4']bisoxazolyl-4-carboxylate | 952413-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2'-(2-bromoacetyl)-5-phenyl[2,4']bisoxazolyl-4-carboxylate
• 英文别名: Methyl 2-[2-(2-bromoacetyl)-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylate
• CAS: 952413-99-9
• 化学式: C₁₆H₁₁BrN₂O₅
• 分子量: 391.178
• InChiKey: JMKJPFAXDJTTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2'-(2-bromoacetyl)-5-phenyl[2,4']bisoxazolyl-4-carboxylate 在 lithium hydroxide 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization

  摘要：

  Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.103
• 作为产物：
  描述：

  methyl 2'-(2-bromo-1,1-dimethoxyethyl)-5-phenyl-[2,4']bis-oxazolyl-4-carboxylate 在 甲酸 作用下， 反应 2.0h， 以91%的产率得到methyl 2'-(2-bromoacetyl)-5-phenyl[2,4']bisoxazolyl-4-carboxylate
  参考文献：
  名称：

  Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization

  摘要：

  Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.103