11-cyclopentenylundec-10-yn-5-one | 1313885-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-cyclopentenylundec-10-yn-5-one
• 英文别名: 11-(Cyclopenten-1-yl)undec-10-yn-5-one
• CAS: 1313885-31-2
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: KMUIUFXOWURDFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-n-butylcyclohept-1-ene 在 copper(l) iodide 、 全氟丁基磺酰氟 、 臭氧 、 二异丙胺 、 三苯基膦 、 (叔丁基亚氨基)三(吡咯烷)膦 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 11-cyclopentenylundec-10-yn-5-one
  参考文献：
  名称：

  Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation—base catalyzed elimination sequence

  摘要：

  Keto aldehydes were selectively converted to non-conjugated alkynyl ketones possessing an unsubstituted alkyne terminus using one-pot nonaflation-base catalyzed elimination reaction sequences. Consecutive one-pot nonaflation of keto aldehydes with perfluorobutane-l-sulfonyl fluoride and elimination of the nonaflyl group using the P(1) phosphazene base resulted in the formation of a terminal C C triple bond with the keto group remaining intact. Careful optimization of the reaction conditions enabled a highly chemoselective conversion of the aldehyde function in the presence of unprotected keto groups exploiting a minor difference in acidity of their alpha-hydrogen atoms. Scope and limitations of the protocol as well as possible implementation of these substrates in Sonogashira coupling were explored. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.095