2-[Bis(diphenylphosphanylmethyl)amino]acetic acid | 76645-88-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[Bis(diphenylphosphanylmethyl)amino]acetic acid
• CAS: 76645-88-0
• 化学式: C₂₈H₂₇NO₂P₂
• 分子量: 471.475
• InChiKey: AGUGODRHUVFQRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[Bis(diphenylphosphanylmethyl)amino]acetic acid 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以77%的产率得到bis((diphenylphosphoryl)methyl)glycine
  参考文献：
  名称：

  A Simple Procedure to Ditertiary Phosphinocarboxylic Acids and Their Bisphosphine Oxides

  摘要：

  A simple two-step route to a series of carboxylic acid functionalized ditertiary phosphine oxides is described, including the X-ray crystal structures of three representative examples namely {Ph2P(O)CH2}(2)N(CH2)(n)CO2H (n = 35). Strong intermolecular OHO H-bonding is observed in all cases leading to distinct packing arrangements.

  DOI：

  10.1080/10426507.2012.743133
• 作为产物：
  描述：

  二苯基膦 以 甲醇 为溶剂， 反应 21.0h， 生成 2-[Bis(diphenylphosphanylmethyl)amino]acetic acid
  参考文献：
  名称：

  新型双(二膦)铼(V)二氧配合物的合成及抗菌活性

  摘要：

  铼基金属药物最近被强调为对抗多重耐药 (MDR) 病原体的新抗生素的有希望的候选者。一种新的铼 ( V ) 二氧配合物由易于获得的二膦配体制备而成，已被证明对金黄色葡萄球菌( S. aureus ) 和白色念珠菌( C. albicans ) 具有强效活性，同时对人体细胞毒性低。

  DOI：

  10.1039/d2dt02157a

文献信息

• Optisch aktive N-phosphinomethylierte α-aminosäuren: synthese und anwendung als liganden in asymmetrischen hydrierungen mit rhodium-komplexen
  作者：K. Kellner、A. Tzschach、Z. Nagy-Magos、L. Markó

  DOI：10.1016/s0022-328x(00)90290-0

  日期：1980.7

  α-Aminoacids, their esters and sodium salts may be transformed by a modified Mannich-reaction into N-phosphinomethyl or N,N-bis(phosphinomethyl) derivatives. The sodium or triethylammonium salts of the chiral bisphosphines l-()-N,N-bis(diphenylphosphinomethyl)-alanine and -valine may be used as ligands to form enantioselective hydrogenation catalysts with rhodium complexes. The highest optical yield

  α-氨基酸，它们的酯和钠盐可通过修饰的曼尼希反应转化为N-膦甲基或N，N-双（膦甲基）衍生物。手性双膦-1-（N）-N，N-双（二苯基膦甲基）-丙氨酸和-缬氨酸的钠或三乙铵盐可以用作配体，以与铑配合物形成对映选择性氢化催化剂。达到的最高光学产率为29％。
• Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: structures, solution behavior and cytotoxicity
  作者：Jianyong Zhang、Jagadese J. Vittal、William Henderson、Jessica R. Wheaton、Iris H. Hall、T.S.Andy Hor、Yaw Kai Yan

  DOI：10.1016/s0022-328x(02)01200-7

  日期：2002.5

  [ReBr(CO)3(Ph2PCH2)2NCH2]2 (12). All new complexes have been characterized by NMR and IR spectroscopy and for 7, 9 and 10, single-crystal X-ray diffraction analyses. Electrospray mass spectrometric studies show that the rhenium–phosphine chelates are very stable, especially in neutral methanolic solution. Hydrolysis of the ester and amide linkages slowly occur in acidic and basic solutions over several weeks;

  胺，氨基酸和模型肽与Ph 2 PH和CH 2 O的修饰曼尼希反应得到双（二苯基膦甲基）胺（Ph 2 PCH 2）2 NR [R = Ph（1），CH 2 CH 2 OH（2） ，CH 2 COOCH 2 Ph（3），CH 2 CONHCH 2 COOCH 2 Ph（4），CH 2 COOH（5）]和（Ph 2 PCH 2）2 NCH 2 CH 2 N（CH2 PPh 2）2（6）。在温和条件下与[ReBr 3（CO）3 ] 2-反应生成[ReBr（CO）3 ] （Ph 2 PCH 2）2 NR} [R = Ph（7），CH 2 CH 2 OH（8） ，CH 2 COOCH 2 Ph（9），CH 2 CONHCH 2 COOCH 2 Ph（10），CH 2 COOH（11）]和[ReBr（CO）3（Ph 2PCH 2）2 NCH 2 ] 2（12）。所有新的复合物的特点是NMR和IR光谱以
• Kellner, Kurt; Hanke, Wolfgang; Tzschach, Alfred, Zeitschrift fur Chemie, 1984, vol. 24, # 5, p. 193 - 194
  作者：Kellner, Kurt、Hanke, Wolfgang、Tzschach, Alfred

  DOI：——

  日期：——
• The Influence of the Second and Outer Coordination Spheres on Rh(diphosphine)₂ CO₂ Hydrogenation Catalysts
  作者：J. Timothy Bays、Nilusha Priyadarshani、Matthew S. Jeletic、Elliot B. Hulley、Deanna L. Miller、John C. Linehan、Wendy J. Shaw

  DOI：10.1021/cs5009199

  日期：2014.10.3

  A series of [Rh((PCH2XCH2P)-C-R)(2)](+) complexes was prepared to investigate second and outer coordination sphere effects on CO2 hydrogenation catalysis, where X is CH2 (dppp) or X-R is N-CH3, N-CH2COOH (glycine), N-CH2COOCH3 (Gly-OMe), or N-CH2C(O)N-CH(CH3)-COOCH3 (GlyAla-OMe). All of these complexes were active for CO2 reduction to formate, with the N-CH3 derivative offering an 8-fold enhancement over the dppp derivative, which is consistent with increased electron density around the metal. Despite the increase in rate with the addition of the pendant nitrogen, the addition of electron withdrawing amino acids and dipeptides to the amine resulted in complexes with reductions in rate of 1 to 2 orders of magnitude, most consistent with a change in pK(a) of the pendant amine, resulting in lower activity. Collectively, the data suggest multiple contributions of the pendant amine in this catalytic system.
• KELLNER, K.;HANKE, W.;TZSCHACH, A., Z. CHEM., 1984, 24, N 5, 193-194
  作者：KELLNER, K.、HANKE, W.、TZSCHACH, A.

  DOI：——

  日期：——