(S)-14,16-dimethoxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-1-one | 1630030-50-0

• 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)-14,16-dimethoxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-1-one
• CAS: 1630030-50-0
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: SYKLZASIUCGHOT-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-14,16-dimethoxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-1-one 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.5h， 以38%的产率得到Zearalane
  参考文献：
  名称：

  Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling

  摘要：

  A macrocyclic Cu-catalyzed Sonogashira-type cross-coupling reaction has been developed that employs an operationally simple CuCl/phen/Cs2CO3 catalyst system. Macrocyclizations can be performed at relatively high concentrations without the need for slow addition techniques and form macrocycles with various ring sizes and functional groups. The optimized protocol was employed in the synthesis of (S)-zearalane, demonstrating applicability toward the synthesis of a macrocycle with known biological activity.

  DOI：

  10.1021/ol501898b
• 作为产物：
  描述：

  (R)-(+)-3-undecyn-2-ol 在 1,10-菲罗啉 、 偶氮二甲酸二异丙酯 、 50 mol% Pd/C 、 氢气 、 sodium hydride 、 caesium carbonate 、 乙二胺 、 三苯基膦 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 135.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 (S)-14,16-dimethoxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-1-one
  参考文献：
  名称：

  Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling

  摘要：

  A macrocyclic Cu-catalyzed Sonogashira-type cross-coupling reaction has been developed that employs an operationally simple CuCl/phen/Cs2CO3 catalyst system. Macrocyclizations can be performed at relatively high concentrations without the need for slow addition techniques and form macrocycles with various ring sizes and functional groups. The optimized protocol was employed in the synthesis of (S)-zearalane, demonstrating applicability toward the synthesis of a macrocycle with known biological activity.

  DOI：

  10.1021/ol501898b