(4S,25E)-31-hydroxy-29-methoxy-4-methyl-3,13,18-trioxa-9,22-diazabicyclo[25.4.0]hentriaconta-1(27),25,28,30-tetraene-2,8,23-trione | 1200112-48-6

• 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: (4S,25E)-31-hydroxy-29-methoxy-4-methyl-3,13,18-trioxa-9,22-diazabicyclo[25.4.0]hentriaconta-1(27),25,28,30-tetraene-2,8,23-trione
• CAS: 1200112-48-6
• 化学式: C₂₈H₄₂N₂O₈
• 分子量: 534.65
• InChiKey: JZJMTLSQQCQJNT-ISPXXFMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4,8-二氧-十二烷-1,12-二胺 、 (S)-6-(2-chloroethoxy)-6-oxohexan-2-yl (E)-2-(4-(2-chloroethoxy)-4-oxobut-1-en-1-yl)-6-hydroxy-4-methoxybenzoate 在 Chirazyme-L₉ 、 sodium sulfate 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以83%的产率得到(4S,25E)-31-hydroxy-29-methoxy-4-methyl-3,13,18-trioxa-9,22-diazabicyclo[25.4.0]hentriaconta-1(27),25,28,30-tetraene-2,8,23-trione
  参考文献：
  名称：

  Application of combinatorial biocatalysis for a unique ring expansion of dihydroxymethylzearalenone

  摘要：

  Combinatorial biocatalysis was applied to generate a diverse set of dihydroxymethylzearalenone analogs with modified ring structure. In one representative chemoenzymatic reaction sequence, dihydroxymethylzearalenone was first subjected to a unique enzyme-catalyzed oxidative ring opening reaction that creates two new carboxylic groups on the molecule. These groups served as reaction sites for further derivatization involving biocatalytic ring closure reactions with structurally diverse bifunctional reagents, including different diols and diamines. As a result, a library of cyclic bislactones and bislactams was created, with modified ring structures covering chemical space and structure activity relationships unattainable by conventional synthetic means. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.04.005

文献信息

• Application of combinatorial biocatalysis for a unique ring expansion of dihydroxymethylzearalenone
  作者：Joseph O. Rich、Cheryl L. Budde、Luke D. McConeghey、Ian C. Cotterill、Vadim V. Mozhaev、Sheo B. Singh、Michael A. Goetz、Annie Zhao、Peter C. Michels、Yuri L. Khmelnitsky

  DOI：10.1016/j.bmcl.2009.04.005

  日期：2009.6

  Combinatorial biocatalysis was applied to generate a diverse set of dihydroxymethylzearalenone analogs with modified ring structure. In one representative chemoenzymatic reaction sequence, dihydroxymethylzearalenone was first subjected to a unique enzyme-catalyzed oxidative ring opening reaction that creates two new carboxylic groups on the molecule. These groups served as reaction sites for further derivatization involving biocatalytic ring closure reactions with structurally diverse bifunctional reagents, including different diols and diamines. As a result, a library of cyclic bislactones and bislactams was created, with modified ring structures covering chemical space and structure activity relationships unattainable by conventional synthetic means. Published by Elsevier Ltd.