N,N'-bis(3-phosphanylpropyl)phthalamide | 259544-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(3-phosphanylpropyl)phthalamide
• 英文别名: 1-N,2-N-bis(3-phosphanylpropyl)benzene-1,2-dicarboxamide
• CAS: 259544-57-5
• 化学式: C₁₄H₂₂N₂O₂P₂
• 分子量: 312.288
• InChiKey: ZUVNQRFTKWOGTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N,N'-bis(3-phosphanylpropyl)phthalamide 以 乙醇 为溶剂， 反应 0.5h， 生成 N,N'-bis[3-(bis(hydroxymethyl)phosphanyl)propyl]phthalamide
  参考文献：
  名称：

  Facile Ring-Opening Reactions of Phthalimides as a New Strategy to Synthesize Amide-Functionalized Phosphonates, Primary Phosphines, and Bisphosphines

  摘要：

  The nucleophile-assisted ring-opening reaction of phthalimides 1 has been studied. The reaction of phthalimides 1 with 0.5 equiv of hydrazine produced the novel bisphosphonates 2 in near quantitative yields whereas with 10-fold excess of hydrazine, diethyl aminoalkylphosphonates 3 was formed in 75% yields. The reaction of phthalimide Ib with 3-(aminopropyl)phosphine resulted in a novel compound 4a containing a P-III hydride and a P-V phosphonate within the same molecule. In addition, the reaction of Ib with 2-aminoethanol and 2-aminoethanethiol resulted in the formation of new phosphonates 4b,c. The reaction of bisphosphonates 2 with LiAlH4 in THF at 0 degrees C selectively reduced the phosphonate groups producing corresponding air-stable primary bisphosphines 6 in 80% yields. Further, the formylation of bisphosphines 6 under very mild conditions using 37% aqueous formaldehyde produced the corresponding novel water-soluble bisphosphine chelating agents 7 in near quantitative yields. All the new compounds have been characterized by H-1, C-13, P-31 NMR, IR spectroscopy and mass spectrometry.

  DOI：

  10.1021/jo991067b
• 作为产物：
  描述：

  (3-{2-[3-(diethoxyphosphoryl)propylcarbamoyl]benzoylamino}propyl)phosphonic acid diethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以81%的产率得到N,N'-bis(3-phosphanylpropyl)phthalamide
  参考文献：
  名称：

  Facile Ring-Opening Reactions of Phthalimides as a New Strategy to Synthesize Amide-Functionalized Phosphonates, Primary Phosphines, and Bisphosphines

  摘要：

  The nucleophile-assisted ring-opening reaction of phthalimides 1 has been studied. The reaction of phthalimides 1 with 0.5 equiv of hydrazine produced the novel bisphosphonates 2 in near quantitative yields whereas with 10-fold excess of hydrazine, diethyl aminoalkylphosphonates 3 was formed in 75% yields. The reaction of phthalimide Ib with 3-(aminopropyl)phosphine resulted in a novel compound 4a containing a P-III hydride and a P-V phosphonate within the same molecule. In addition, the reaction of Ib with 2-aminoethanol and 2-aminoethanethiol resulted in the formation of new phosphonates 4b,c. The reaction of bisphosphonates 2 with LiAlH4 in THF at 0 degrees C selectively reduced the phosphonate groups producing corresponding air-stable primary bisphosphines 6 in 80% yields. Further, the formylation of bisphosphines 6 under very mild conditions using 37% aqueous formaldehyde produced the corresponding novel water-soluble bisphosphine chelating agents 7 in near quantitative yields. All the new compounds have been characterized by H-1, C-13, P-31 NMR, IR spectroscopy and mass spectrometry.

  DOI：

  10.1021/jo991067b

文献信息

• Facile Ring-Opening Reactions of Phthalimides as a New Strategy to Synthesize Amide-Functionalized Phosphonates, Primary Phosphines, and Bisphosphines
  作者：Hariprasad Gali、Kandikere R. Prabhu、Srinivasa R. Karra、Kattesh V. Katti

  DOI：10.1021/jo991067b

  日期：2000.2.1

  The nucleophile-assisted ring-opening reaction of phthalimides 1 has been studied. The reaction of phthalimides 1 with 0.5 equiv of hydrazine produced the novel bisphosphonates 2 in near quantitative yields whereas with 10-fold excess of hydrazine, diethyl aminoalkylphosphonates 3 was formed in 75% yields. The reaction of phthalimide Ib with 3-(aminopropyl)phosphine resulted in a novel compound 4a containing a P-III hydride and a P-V phosphonate within the same molecule. In addition, the reaction of Ib with 2-aminoethanol and 2-aminoethanethiol resulted in the formation of new phosphonates 4b,c. The reaction of bisphosphonates 2 with LiAlH4 in THF at 0 degrees C selectively reduced the phosphonate groups producing corresponding air-stable primary bisphosphines 6 in 80% yields. Further, the formylation of bisphosphines 6 under very mild conditions using 37% aqueous formaldehyde produced the corresponding novel water-soluble bisphosphine chelating agents 7 in near quantitative yields. All the new compounds have been characterized by H-1, C-13, P-31 NMR, IR spectroscopy and mass spectrometry.