[4-[2-[[(2R,3S)-6-(4-hydroxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-(2-methylpropyl)hexanoyl]amino]ethyl]phenyl]boronic acid | 339221-06-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [4-[2-[[(2R,3S)-6-(4-hydroxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-(2-methylpropyl)hexanoyl]amino]ethyl]phenyl]boronic acid
• CAS: 339221-06-6
• 化学式: C₂₉H₄₂BNO₆
• 分子量: 511.467
• InChiKey: LDQWKTLOPDKZKC-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-[2-[[(2R,3S)-6-(4-hydroxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-(2-methylpropyl)hexanoyl]amino]ethyl]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43%的产率得到(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
• 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 、 PdCl₂(pddf) 、 氢气 、 potassium acetate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 lithium diisopropyl amide 、 苯硼酸 作用下， 以 甲醇 、 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 40.0h， 生成 [4-[2-[[(2R,3S)-6-(4-hydroxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-(2-methylpropyl)hexanoyl]amino]ethyl]phenyl]boronic 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

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.