(3-aminopropyl)phosphine | 5689-80-5

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: (3-aminopropyl)phosphine
• 英文别名: 3-aminopropylphopsphine；3-aminopropylphosphine；3-phosphino-propylamine；3-Phosphino-propylamin；3-Phosphanyl-propylamine；3-phosphanylpropan-1-amine
• CAS: 5689-80-5
• 化学式: C₃H₁₀NP
• 分子量: 91.0929
• InChiKey: OTABLIMKXCPLGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  5
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-aminopropyl)phosphine 、 甲基丙二酸二甲酯 反应 12.0h， 以70%的产率得到2-Methyl-N,N'-bis-(3-phosphanyl-propyl)-malonamide
  参考文献：
  名称：

  前所未有的选择性氨解：氨基丙基膦作为新系列空气稳定的单、双和三伯膦的构建块

  摘要：

  使用初级和次级膦作为开发新化学的通用试剂的一个严重障碍与它们令人不快的自燃性质和极端的水解、热和氧化不稳定性有关。特别是，具有“用户友好”特性（例如，良好的氧化/热稳定性，低挥发性）的初级膦不仅从合成的角度来看而且对于潜在的应用（例如在树枝状聚合物的形成中）都非常重要。作为对官能化磷化合物的基本主基团和有机化学正在进行的研究的一部分，作者在本文中报告说，3-氨基丙基伯膦 3 与甲基酯在游离酸、酰胺、和硫醇产生空气稳定的酰胺、羧酸盐、

  DOI：

  10.1021/ja993504+
• 作为产物：
  描述：

  diethyl 3-azidopropylphosphonate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以65%的产率得到(3-aminopropyl)phosphine
  参考文献：
  名称：

  前所未有的选择性氨解：氨基丙基膦作为新系列空气稳定的单、双和三伯膦的构建块

  摘要：

  使用初级和次级膦作为开发新化学的通用试剂的一个严重障碍与它们令人不快的自燃性质和极端的水解、热和氧化不稳定性有关。特别是，具有“用户友好”特性（例如，良好的氧化/热稳定性，低挥发性）的初级膦不仅从合成的角度来看而且对于潜在的应用（例如在树枝状聚合物的形成中）都非常重要。作为对官能化磷化合物的基本主基团和有机化学正在进行的研究的一部分，作者在本文中报告说，3-氨基丙基伯膦 3 与甲基酯在游离酸、酰胺、和硫醇产生空气稳定的酰胺、羧酸盐、

  DOI：

  10.1021/ja993504+

文献信息

• Prabhu; Kishore; Gali, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S237-S239
  作者：Prabhu、Kishore、Gali、Jimenez、Simmons、Katti、Volkert

  DOI：——

  日期：——
• Phospha Derivatives of Tris(2-aminoethyl)amine (<i>tren</i>) and Tris(3-aminopropyl)amine (<i>trpn</i>): Synthesis and Complexation Studies with Group 4 Metals
  作者：Malte Sietzen、Sonja Batke、Lukas Merz、Hubert Wadepohl、Joachim Ballmann

  DOI：10.1021/acs.organomet.5b00065

  日期：2015.3.23

  The N,N',N ''-triphenyl-substituted derivative of tris(2-aminoethyl)phosphine (Ph-3-phospha-tren, P(CH2CH2NHR)(3), R = Ph) and four derivatives of the related tris(3-aminopropyl)phosphine (phospha-trpn, P(CH2CH2CH2NHR)(3), R = Pr-i, Bu-t, (SiBuMe2)-Bu-t, Ph) have been synthesized in addition to the parent phospha-trpn. Out of these ligand systems, only the N,N',N ''-triphenyl-substituted phospha-trpn derivative P(CH2CH2CH2NHPh)(3) was found to be suitable for coordination to group 4 metals. For titanium, zirconium, and hafnium, the C-3-symmetric endo-P-configured dimethylamido complexes Ph[PN3]M(NMe2) of the former ligand have been prepared and converted into the corresponding triflates Ph[PN3]M(OTf). Starting from these triflates, the benzyl complexes Ph[PN3]M(Bn) (M = Ti, Zr, Hf) have been obtained via reaction with Bn2Mg(THF)(2). In case of titanium, the benzyl species Ph[PN3]Ti(Bn) is prone to thermal elimination of toluene, which results in the formation of a cyclometalated species. These findings are discussed in context with the very few group 4 trisamidophosphine complexes that have been reported earlier.
• 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.
• The Preparation of Organo-phosphines by the Addition of Phosphine to Unsaturated Compounds
  作者：A. R. Stiles、F. F. Rust、W. E. Vaughan

  DOI：10.1021/ja01133a018

  日期：1952.7
• Process for producing organic phosphines
  申请人：SHELL DEV

  公开号：US02803597A1

  公开（公告）日：1957-08-20