(8S,11R,12S)-11-Isobutyl-8-methylcarbamoyl-10-oxo-2-oxa-9-aza-tricyclo[14.2.2.2^3,6]docosa-1(19),3,5,16(20),17,21-hexaene-12-carboxylic acid tert-butyl ester | 339221-10-2

• 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: (8S,11R,12S)-11-Isobutyl-8-methylcarbamoyl-10-oxo-2-oxa-9-aza-tricyclo[14.2.2.2^3,6]docosa-1(19),3,5,16(20),17,21-hexaene-12-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (8S,11R,12S)-8-(methylcarbamoyl)-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-12-carboxylate
• CAS: 339221-10-2
• 化学式: C₃₁H₄₂N₂O₅
• 分子量: 522.685
• InChiKey: MZIVCZUPVAPWQN-VJGNERBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8S,11R,12S)-11-Isobutyl-8-methylcarbamoyl-10-oxo-2-oxa-9-aza-tricyclo[14.2.2.2^3,6]docosa-1(19),3,5,16(20),17,21-hexaene-12-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (8S,11R,12S)-11-Isobutyl-8-methylcarbamoyl-10-oxo-2-oxa-9-aza-tricyclo[14.2.2.2^3,6]docosa-1(19),3,5,16(20),17,21-hexaene-12-carboxylic acid
  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：

  [4-[(2S)-2-[[(2R,3S)-6-(4-hydroxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-(2-methylpropyl)hexanoyl]amino]-3-(methylamino)-3-oxopropyl]phenyl]boronic acid 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以52%的产率得到(8S,11R,12S)-11-Isobutyl-8-methylcarbamoyl-10-oxo-2-oxa-9-aza-tricyclo[14.2.2.2^3,6]docosa-1(19),3,5,16(20),17,21-hexaene-12-carboxylic acid tert-butyl ester
  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