PhNHCH2CH2PCy2 | 1365973-63-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: PhNHCH2CH2PCy2
• 英文别名: N-(2-dicyclohexylphosphanylethyl)aniline
• CAS: 1365973-63-2
• 化学式: C₂₀H₃₂NP
• 分子量: 317.455
• InChiKey: VULZHWFIKLPMBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  PhNHCH2CH2PCy2 、 双(三甲基硅烷基)氨基钾 、 iron(II) chloride 以 四氢呋喃 为溶剂， 以67%的产率得到Fe(PhNCH2CH2PCy2)2
  参考文献：
  名称：

  Iron Complex-Catalyzed Ammonia–Borane Dehydrogenation. A Potential Route toward B–N-Containing Polymer Motifs Using Earth-Abundant Metal Catalysts

  摘要：

  Ammonia-borane (NH3BH3, AB) has garnered interest as a hydrogen storage material due to its high weight percent hydrogen content and ease of H-2 release relative to metal hydrides. As a consequence of dehydrogenation, B-N-containing oligomeric/polymeric materials are formed. The ability to control this process and dictate the identity of the generated polymer opens up the possibility of the targeted synthesis of new materials. While precious metals have been used in this regard, the ability to construct such materials using earth-abundant metals such as Fe presents a more economical approach. Four Fe complexes containing amido and phosphine supporting ligands were synthesized, and their reactivity with AB was examined. Three-coordinate Fe(PCy3)[N(SiMe3)(2)](2) (1) and four-coordinate Fe(DEPE)[N(SiMe3)(2)](2) (2) yield a mixture of (NH2BH2) and (NHBH)(n) products with up to 1.7 equiv of H-2 released per AB but cannot be recycled (DEPE = 1,2-bis(diethylphosphino)ethane). In contrast, Fe supported by a bidentate P-N ligand (4) can be used in a second cycle to afford a similar product mixture. Intriguingly, the symmetric analogue of 4 (Fe(N-N)(P-P), 3), only generates (NH2BH2) and does so in minutes at room temperature. This marked difference in reactivity may be the result of the chemistry of Fe(II) vs Fe(0).

  DOI：

  10.1021/ja210542r
• 作为产物：
  描述：

  N-苯基乙醇胺 在 盐酸 、 正丁基锂 、 六氯乙烷 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 122.0h， 生成 PhNHCH2CH2PCy2
  参考文献：
  名称：

  Iron Complex-Catalyzed Ammonia–Borane Dehydrogenation. A Potential Route toward B–N-Containing Polymer Motifs Using Earth-Abundant Metal Catalysts

  摘要：

  Ammonia-borane (NH3BH3, AB) has garnered interest as a hydrogen storage material due to its high weight percent hydrogen content and ease of H-2 release relative to metal hydrides. As a consequence of dehydrogenation, B-N-containing oligomeric/polymeric materials are formed. The ability to control this process and dictate the identity of the generated polymer opens up the possibility of the targeted synthesis of new materials. While precious metals have been used in this regard, the ability to construct such materials using earth-abundant metals such as Fe presents a more economical approach. Four Fe complexes containing amido and phosphine supporting ligands were synthesized, and their reactivity with AB was examined. Three-coordinate Fe(PCy3)[N(SiMe3)(2)](2) (1) and four-coordinate Fe(DEPE)[N(SiMe3)(2)](2) (2) yield a mixture of (NH2BH2) and (NHBH)(n) products with up to 1.7 equiv of H-2 released per AB but cannot be recycled (DEPE = 1,2-bis(diethylphosphino)ethane). In contrast, Fe supported by a bidentate P-N ligand (4) can be used in a second cycle to afford a similar product mixture. Intriguingly, the symmetric analogue of 4 (Fe(N-N)(P-P), 3), only generates (NH2BH2) and does so in minutes at room temperature. This marked difference in reactivity may be the result of the chemistry of Fe(II) vs Fe(0).

  DOI：

  10.1021/ja210542r

文献信息

• Iron Complex-Catalyzed Ammonia–Borane Dehydrogenation. A Potential Route toward B–N-Containing Polymer Motifs Using Earth-Abundant Metal Catalysts
  作者：R. Tom Baker、John C. Gordon、Charles W. Hamilton、Neil J. Henson、Po-Heng Lin、Steven Maguire、Muralee Murugesu、Brian L. Scott、Nathan C. Smythe

  DOI：10.1021/ja210542r

  日期：2012.3.28

  Ammonia-borane (NH3BH3, AB) has garnered interest as a hydrogen storage material due to its high weight percent hydrogen content and ease of H-2 release relative to metal hydrides. As a consequence of dehydrogenation, B-N-containing oligomeric/polymeric materials are formed. The ability to control this process and dictate the identity of the generated polymer opens up the possibility of the targeted synthesis of new materials. While precious metals have been used in this regard, the ability to construct such materials using earth-abundant metals such as Fe presents a more economical approach. Four Fe complexes containing amido and phosphine supporting ligands were synthesized, and their reactivity with AB was examined. Three-coordinate Fe(PCy3)[N(SiMe3)(2)](2) (1) and four-coordinate Fe(DEPE)[N(SiMe3)(2)](2) (2) yield a mixture of (NH2BH2) and (NHBH)(n) products with up to 1.7 equiv of H-2 released per AB but cannot be recycled (DEPE = 1,2-bis(diethylphosphino)ethane). In contrast, Fe supported by a bidentate P-N ligand (4) can be used in a second cycle to afford a similar product mixture. Intriguingly, the symmetric analogue of 4 (Fe(N-N)(P-P), 3), only generates (NH2BH2) and does so in minutes at room temperature. This marked difference in reactivity may be the result of the chemistry of Fe(II) vs Fe(0).