furfuryl-2-(N-diphenylphosphino)methylamine | 586985-91-3

• 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: furfuryl-2-(N-diphenylphosphino)methylamine
• 英文别名: furfuryl-2-(N-diphenylphosphino)amine；furfuryl-(N-diphenylphosphino)amine；furfuryl-N-(diphenylphosphino)amine；[Ph2PNHCH2-C4H3O]；Ph2PNHCH2-C4H3O；Ph2PNHCH2(C4H3O)；N-diphenylphosphanyl-1-(furan-2-yl)methanamine
• CAS: 586985-91-3
• 化学式: C₁₇H₁₆NOP
• 分子量: 281.294
• InChiKey: QJGGQRJWFPLZPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (COD)Pd(Me)2 、 furfuryl-2-(N-diphenylphosphino)methylamine 以 四氢呋喃 为溶剂， 以87.5%的产率得到cis-dimethylbis(furfuryl-2-(N-diphenylphosphino)methylamine)palladium(II)
  参考文献：
  名称：

  Aminophosphine–palladium(II) complexes: Synthsesis, structure and applications in Suzuki and Heck cross-coupling reactions

  摘要：

  Reaction of furfurylamine with 1 or 2 equivalents of PPh2Cl in the presence of Et3N, proceeds under anaerobic conditions in thf to give furfuryl-2-(N-diphenylphosphino)amine, Ph2PNHCH2-C4H3O, 1 and furfuryl-2-(N,N-bis(diphenylphosphino)amine), (Ph2P)(2)NCH2-C4H3O, 2, respectively. The reactions of 1 and 2 with MCl2(cod) (M = Pd, Pt; cod = 1,5-cyclooctadiene) or Pt(CH3)(2)(cod) yield complexes [M(Ph2PNHCH2-C4H3O)(2)Cl-2] (M= Pd 1a, Pt 1b), [Pt(Ph2PNHCH2-C4H3O)(2)(CH3)(2)] (1c), and [M((Ph2P)(2) NCH2-C4H3O)Cl-2] (M= Pd 2a, Pt 2b), [Pt((Ph2P)(2)NCH2-C4H3O)(CH3)(2)] (2c), respectively. All the compounds were isolated as analytically pure substances and characterized by NMR, IR spectroscopy and elemental analysis. Representative solid-state structures of 2a and 2b were also determined by X-ray single crystal diffraction technique. Furthermore, the palladium complexes 1a and 2a were tested and found to be highly active catalysts in the Suzuki coupling and Heck reaction affording biphenyls and trans-stilbenes, respectively. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.07.056
• 作为产物：
  描述：

  2-呋喃甲胺 、 二苯基氯化膦 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91.1%的产率得到furfuryl-2-(N-diphenylphosphino)methylamine
  参考文献：
  名称：

  用于芳族酮转移加氢的金属催化剂的模块化设计

  摘要：

  过渡金属催化剂通过转移氢化从有机底物中添加或除去氢的能力是一种有价值的合成工具。针对一系列具有P-NH配体的新型金属配合物，合成了糠胺衍生的[Ph 2 PNHCH 2 -C 4 H 3 O]。的反应[PH 2 PNHCH 2 -C 4 ħ 3 O] 1用的[Ru（η 6 - p -cymene）（μ-Cl）的CL] 2，[茹（η 6 -苯）（μ-Cl）的CL] 2，的[Rh（μ-Cl）的（COD）] 2和物[Ir（η 5 -C 5我5）（μ-Cl）的CL] 2给出了一系列新的单齿络合物的[Ru（PH 2 PNHCH 2 -C 4 ħ 3 O）（η 6 - p -cymene）氯2 ] 2，[茹（PH 2 PNHCH 2 -C 4 ħ 3 O）（η 6 -苯）氯2 ] 3，[铑（PH 2 PNHCH 2 -C 4 ħ 3 O）（COD）CL] 4和[Ir（PH 2 PNHCH 2 -C 4小时30）（η

  DOI：

  10.1002/aoc.1853

文献信息

• Ruthenium, rhodium and iridium complexes of the furfuryl-2-(N-diphenylphosphino)methylamine ligand: Molecular structure and catalytic activity
  作者：Cezmi Kayan、Nermin Meric、Murat Aydemir、Akın Baysal、Duygu Elma、Bünyamin Ak、Ertan Şahin、Nevin Gürbüz、İsmail Özdemir

  DOI：10.1016/j.poly.2012.05.009

  日期：2012.7

  The reaction of furfurylamine with two equivalents of PPh2Cl in the presence of Et3N affords furfuryl-2-(N,N-bis(diphenylphosphino)amine), (Ph2P)(2)NCH2-C4H3O (1). The corresponding ruthenium(II) complex trans-[Ru((PPh2)(2)NCH2-C4H3O)(2)Cl-2] (3) was synthesized by reacting 1 with [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2). The reaction of furfurylamine with one equivalent of PPh2Cl gives Ph2PNHCH2-C4H3O (2). The reaction of 2 with [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2), [Ru(eta(6)-benzene)(mu-Cl)Cl](2), [Rh(mu-Cl)(cod)](2) and [Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) yields the complexes [Ru(Ph2PNHCH2-C4H3S)(eta(6)-p-cymene)Cl-2] (4), [Ru(Ph2PNHCH2-C4H3O)(eta(6-)benzene)Cl-2] (5), [Rh(Pb2PNHCH2-C4H3O)(cod)Cl] (6) and [Ir(Ph2PNHCH2-C4H3O)(eta(5)-C5Me5)Cl-2] (7), respectively. All the complexes were isolated from the reaction solution and fully characterized by analytical and spectroscopic methods. The structure of [Ru(Ph2PNHCH2-C4H3O)(eta(6)-p-cymene)Cl-2] (4) was also determined by single crystal X-ray diffraction. Complexes 3-7 are suitable precursors forming highly active catalysts in the transfer hydrogenation of a variety of simple ketones. Notably, the catalysts obtained by using the ruthenium complexes [Ru(Ph2PNHCH2-C4H3O)(eta(6)-p-cymene)Cl-2] (4) and [Ru(Ph2PNHCH2-C4H3O)(eta(6)-benzene)Cl-2] (5) are much more active in the transfer hydrogenation, converting the carbonyls to the corresponding alcohols in 97-99% yields (TOF <= 300 h(-1)), compared to analogous rhodium and iridium complexes and the trans-Ru(II)-p-cymene bis(phosphino)amine complex. (c) 2012 Elsevier Ltd. All rights reserved.