(11R,12S)-11-Isobutyl-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 | 339221-11-3

• 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: (11R,12S)-11-Isobutyl-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 (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-12-carboxylate
• CAS: 339221-11-3
• 化学式: C₂₉H₃₉NO₄
• 分子量: 465.633
• InChiKey: ZXJZHVLEENQTRO-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (11R,12S)-11-Isobutyl-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 (11R,12S)-11-Isobutyl-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：

  (R)-2-(2-(叔丁氧基)-2-氧代乙基)-4-甲基戊酸 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 copper diacetate 、 PdCl₂(pddf) 、 氢气 、 potassium acetate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 lithium diisopropyl amide 、 苯硼酸 作用下， 以 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 88.0h， 生成 (11R,12S)-11-Isobutyl-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

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.