2-methylene-4-(n-butyl)but-3-ynal | 849180-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylene-4-(n-butyl)but-3-ynal
• 英文别名: 2-Methylideneoct-3-ynal
• CAS: 849180-86-5
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: DWPOGBUCMRWASD-UHFFFAOYSA-N

物化性质

• 沸点：
  234.4±23.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  频哪酮 、 2-methylene-4-(n-butyl)but-3-ynal 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以70%的产率得到5-hydroxy-2,2-dimethyl-6-methylene-8-(n-butyl)oct-7-yn-3-one
  参考文献：
  名称：

  A Practical Method for the Synthesis of 2-Alkynylpropenals

  摘要：

  A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.

  DOI：

  10.1021/jo047869a
• 作为产物：
  描述：

  2-hydroxymethyl-1-octen-3-yne 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到2-methylene-4-(n-butyl)but-3-ynal
  参考文献：
  名称：

  A Practical Method for the Synthesis of 2-Alkynylpropenals

  摘要：

  A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.

  DOI：

  10.1021/jo047869a

文献信息

• A Practical Method for the Synthesis of 2-Alkynylpropenals
  作者：Charnsak Thongsornkleeb、Rick L. Danheiser

  DOI：10.1021/jo047869a

  日期：2005.3.1

  A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.