12-O-tert-butyl 8-O-methyl (8S,11R,12S)-11-(2-methylpropyl)-10-oxo-2-oxa-9-azatricyclo[14.2.2.23,6]docosa-1(18),3(22),4,6(21),16,19-hexaene-8,12-dicarboxylate | 339221-09-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 12-O-tert-butyl 8-O-methyl (8S,11R,12S)-11-(2-methylpropyl)-10-oxo-2-oxa-9-azatricyclo[14.2.2.23,6]docosa-1(18),3(22),4,6(21),16,19-hexaene-8,12-dicarboxylate
• CAS: 339221-09-9
• 化学式: C₃₁H₄₁NO₆
• 分子量: 523.67
• InChiKey: RQLOEQKQIULDFF-VJGNERBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12-O-tert-butyl 8-O-methyl (8S,11R,12S)-11-(2-methylpropyl)-10-oxo-2-oxa-9-azatricyclo[14.2.2.23,6]docosa-1(18),3(22),4,6(21),16,19-hexaene-8,12-dicarboxylate 在 盐酸羟胺 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl (8S,11R,12S)-12-(hydroxycarbamoyl)-11-(2-methylpropyl)-10-oxo-2-oxa-9-azatricyclo[14.2.2.23,6]docosa-1(18),3(22),4,6(21),16,19-hexaene-8-carboxylate
  参考文献：
  名称：

  Intramolecular O-Arylation of Phenols with Phenylboronic Acids:  Application to the Synthesis of Macrocyclic Metalloproteinase Inhibitors

  摘要：

  The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and tolerant of common chemical functionality. This methodology should provide a general route to macrocyclic biphenyl ethers.

  DOI：

  10.1021/ol015572i
• 作为产物：
  描述：

  (S)-甲基-2-氨基-3-(4-碘苯基)丙酸甲酯 在 palladium on activated charcoal 、 PdCl₂(pddf) N-甲基吗啉 、 盐酸 、 copper diacetate 、 氢气 、 potassium acetate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 苯硼酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 106.0h， 生成 12-O-tert-butyl 8-O-methyl (8S,11R,12S)-11-(2-methylpropyl)-10-oxo-2-oxa-9-azatricyclo[14.2.2.23,6]docosa-1(18),3(22),4,6(21),16,19-hexaene-8,12-dicarboxylate
  参考文献：
  名称：

  Intramolecular O-Arylation of Phenols with Phenylboronic Acids:  Application to the Synthesis of Macrocyclic Metalloproteinase Inhibitors

  摘要：

  The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and tolerant of common chemical functionality. This methodology should provide a general route to macrocyclic biphenyl ethers.

  DOI：

  10.1021/ol015572i

文献信息

• Intramolecular O-Arylation of Phenols with Phenylboronic Acids:  Application to the Synthesis of Macrocyclic Metalloproteinase Inhibitors
  作者：Carl P. Decicco、Ying Song、David A. Evans

  DOI：10.1021/ol015572i

  日期：2001.4.1

  The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and tolerant of common chemical functionality. This methodology should provide a general route to macrocyclic biphenyl ethers.