bis((R)-2-benzylpyrrolidin-1-yl)methanone | 1218922-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: bis((R)-2-benzylpyrrolidin-1-yl)methanone
• 英文别名: bis[(2R)-2-benzylpyrrolidin-1-yl]methanone
• CAS: 1218922-03-2
• 化学式: C₂₃H₂₈N₂O
• 分子量: 348.488
• InChiKey: BSGGXJXXIVYWSU-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bis((R)-2-benzylpyrrolidin-1-yl)methanone 在 草酰氯 作用下， 反应 16.0h， 生成 (R)-2-benzyl-1-(((R)-2-benzylpyrrolidin-1-yl)chloromethylene)-pyrrolidin-1-ium chloride
  参考文献：
  名称：

  Bis(2-alkylpyrrolidin-1-yl)methylidenes as Chiral Acyclic Diaminocarbene Ligands

  摘要：

  2-Alkylpyrrolidines were used as building blocks for acyclic diaminocarbenes (ADCs). First, ureas were made from the corresponding amines, and then the urns were converted to chloro-amidiniums. The chloroamidiniums served as direct precursors to ADCs, and palladium complexes were made utilizing oxidative addition, whereas lithium halogen exchange was performed to generate rhodium complexes. The carbene ligands were characterized through use of NMR, mass spectrometry, and X-ray analysis, and from X-ray structures, steric parameters were calculated as % V-Bur values. The ability of these ligands to direct stereochemistry and enhance activity was explored in the Suzuki cross-coupling reaction and the 1,2 addition of arylboronic acids to aldehydes.

  DOI：

  10.1021/om901112n
• 作为产物：
  描述：

  光气 、 (2R)-2-苄基吡咯烷 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以76%的产率得到bis((R)-2-benzylpyrrolidin-1-yl)methanone
  参考文献：
  名称：

  Bis(2-alkylpyrrolidin-1-yl)methylidenes as Chiral Acyclic Diaminocarbene Ligands

  摘要：

  2-Alkylpyrrolidines were used as building blocks for acyclic diaminocarbenes (ADCs). First, ureas were made from the corresponding amines, and then the urns were converted to chloro-amidiniums. The chloroamidiniums served as direct precursors to ADCs, and palladium complexes were made utilizing oxidative addition, whereas lithium halogen exchange was performed to generate rhodium complexes. The carbene ligands were characterized through use of NMR, mass spectrometry, and X-ray analysis, and from X-ray structures, steric parameters were calculated as % V-Bur values. The ability of these ligands to direct stereochemistry and enhance activity was explored in the Suzuki cross-coupling reaction and the 1,2 addition of arylboronic acids to aldehydes.

  DOI：

  10.1021/om901112n

文献信息

• Bis(2-alkylpyrrolidin-1-yl)methylidenes as Chiral Acyclic Diaminocarbene Ligands
  作者：David R. Snead、Sebastien Inagaki、Khalil A. Abboud、Sukwon Hong

  DOI：10.1021/om901112n

  日期：2010.4.12

  2-Alkylpyrrolidines were used as building blocks for acyclic diaminocarbenes (ADCs). First, ureas were made from the corresponding amines, and then the urns were converted to chloro-amidiniums. The chloroamidiniums served as direct precursors to ADCs, and palladium complexes were made utilizing oxidative addition, whereas lithium halogen exchange was performed to generate rhodium complexes. The carbene ligands were characterized through use of NMR, mass spectrometry, and X-ray analysis, and from X-ray structures, steric parameters were calculated as % V-Bur values. The ability of these ligands to direct stereochemistry and enhance activity was explored in the Suzuki cross-coupling reaction and the 1,2 addition of arylboronic acids to aldehydes.