(S)-2,4-bis<(2-methoxyethoxy)methyl>zearalenone | 132297-27-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (S)-2,4-bis<(2-methoxyethoxy)methyl>zearalenone
• 英文别名: (S)-2,4-bis[(2-methoxyethoxy)methyl]zearalenone；(4S,12E)-16,18-bis(2-methoxyethoxymethoxy)-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
• CAS: 132297-27-9
• 化学式: C₂₆H₃₈O₉
• 分子量: 494.582
• InChiKey: PMQKFXAQCZJQCD-MRSBXDGLSA-N

物化性质

• 沸点：
  641.8±55.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2,4-bis<(2-methoxyethoxy)methyl>zearalenone 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 216.0h， 以80%的产率得到玉米烯酮
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053
• 作为产物：
  描述：

  (R)-(-)-4-烯基-2-戊醇 在 4-二甲氨基吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 双氧水 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 47.0h， 生成 (S)-2,4-bis<(2-methoxyethoxy)methyl>zearalenone
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053

文献信息

• Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone
  作者：A. Kalivretenos、J. K. Stille、L. S. Hegedus

  DOI：10.1021/jo00008a053

  日期：1991.4

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).