cis-1-Acetyl-3-ethinyl-2,2-dimethyl-cyclobutan | 33877-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1-Acetyl-3-ethinyl-2,2-dimethyl-cyclobutan
• 英文别名: 1-[(1R,3R)-3-ethynyl-2,2-dimethylcyclobutyl]ethanone；(-)-cis-1-Acetyl-3-ethynyl-2,2-dimethylcyclobutane
• CAS: 33877-36-0；33894-39-2
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: WBBSSZJPIAKHQQ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  环戊-1-烯-1-基全氟丁烷-1-磺酸酯 、 cis-1-Acetyl-3-ethinyl-2,2-dimethyl-cyclobutan 在 copper(l) iodide 、 二异丙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.176 g的产率得到1-[(1R,3S)-3-(cyclopentenylethynyl)-2,2-dimethylcyclobutyl]ethanone
  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
• 作为产物：
  描述：

  (-)-α-蒎烯 在 全氟丁基磺酰氟 、 臭氧 、 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 cis-1-Acetyl-3-ethinyl-2,2-dimethyl-cyclobutan
  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