di(3,4-methylenedioxyphenyl)(diisopropylamino)phosphine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: di(3,4-methylenedioxyphenyl)(diisopropylamino)phosphine
• 英文别名: N-[bis(1,3-benzodioxol-5-yl)phosphanyl]-N-propan-2-ylpropan-2-amine
• 化学式: C₂₀H₂₄NO₄P
• 分子量: 373.389
• InChiKey: JPKYTXIKJHLNQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴-1,2-亚甲二氧基苯 、 二氯-N,N-二异丙基亚磷酰胺 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以43%的产率得到di(3,4-methylenedioxyphenyl)(diisopropylamino)phosphine
  参考文献：
  名称：

  A Copper- and Amine-Free Sonogashira Reaction Employing Aminophosphines as Ligands

  摘要：

  An efficient Pd-catalyzed Sonogashira coupling reaction was achieved in the absence of a copper salt or amine with an inorganic base and easily prepared, air-stable aminophosphine ligands in commonly used organic solvents; good to excellent yields were obtained. Under optimized reaction conditions, the Sonogashira coupling reaction occurred selectively when an enyne substrate was employed and no Heck reaction product was detected; acetone-masked acetylene and trimethylsi-lylacetylene can also be efficiently coupled, providing a method to make terminal alkynes.

  DOI：

  10.1021/jo049379o
• 作为试剂：
  描述：

  对溴甲苯 、 1-己炔 在 palladium diacetate potassium carbonate 、 di(3,4-methylenedioxyphenyl)(diisopropylamino)phosphine 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以94%的产率得到1-(p-tolyl)-1-hexyne
  参考文献：
  名称：

  A Copper- and Amine-Free Sonogashira Reaction Employing Aminophosphines as Ligands

  摘要：

  An efficient Pd-catalyzed Sonogashira coupling reaction was achieved in the absence of a copper salt or amine with an inorganic base and easily prepared, air-stable aminophosphine ligands in commonly used organic solvents; good to excellent yields were obtained. Under optimized reaction conditions, the Sonogashira coupling reaction occurred selectively when an enyne substrate was employed and no Heck reaction product was detected; acetone-masked acetylene and trimethylsi-lylacetylene can also be efficiently coupled, providing a method to make terminal alkynes.

  DOI：

  10.1021/jo049379o

文献信息

• A Copper- and Amine-Free Sonogashira Reaction Employing Aminophosphines as Ligands
  作者：Jiang Cheng、Yanhui Sun、Feng Wang、Minjie Guo、Jian-Hua Xu、Yi Pan、Zhaoguo Zhang

  DOI：10.1021/jo049379o

  日期：2004.8.1

  An efficient Pd-catalyzed Sonogashira coupling reaction was achieved in the absence of a copper salt or amine with an inorganic base and easily prepared, air-stable aminophosphine ligands in commonly used organic solvents; good to excellent yields were obtained. Under optimized reaction conditions, the Sonogashira coupling reaction occurred selectively when an enyne substrate was employed and no Heck reaction product was detected; acetone-masked acetylene and trimethylsi-lylacetylene can also be efficiently coupled, providing a method to make terminal alkynes.