undec-10-yn-1-yl 3-iodo-2-naphthoate | 1620513-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: undec-10-yn-1-yl 3-iodo-2-naphthoate
• 英文别名: Undec-10-ynyl 3-iodonaphthalene-2-carboxylate
• CAS: 1620513-51-0
• 化学式: C₂₂H₂₅IO₂
• 分子量: 448.344
• InChiKey: CPXYRUBVJFOUKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  undec-10-yn-1-yl 3-iodo-2-naphthoate 在 1,10-菲罗啉 、 caesium carbonate 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以71%的产率得到3-Oxatricyclo[13.8.0.017,22]tricosa-1(23),15,17,19,21-pentaen-13-yn-2-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
• 作为产物：
  描述：

  10-十一炔醇 、 3-碘萘-2-羧酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以62%的产率得到undec-10-yn-1-yl 3-iodo-2-naphthoate
  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