diethyl (1-amino-1-phenylethyl)phosphonate | 84044-06-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (1-amino-1-phenylethyl)phosphonate
• 英文别名: (1-amino-1-phenyl-ethyl)-phosphonic acid diethyl ester；(1-Amino-1-phenyl-aethyl)-phosphonsaeure-diaethylester；Diethyl (1-amino-1-phenylethyl)phosphonate；1-diethoxyphosphoryl-1-phenylethanamine
• CAS: 84044-06-4
• 化学式: C₁₂H₂₀NO₃P
• 分子量: 257.269
• InChiKey: MQWGTNIGZIPNHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  363.0±35.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1-amino-1-phenylethyl)phosphonate 在 盐酸 作用下， 生成 (R,S)-α-amino-α-methylbenzylphosphonic acid
  参考文献：
  名称：

  Optically active?-aminoethylphosphonic acids and their ethyl esters

  摘要：

  DOI：

  10.1007/bf00928530
• 作为产物：
  描述：

  苯乙酮 在 盐酸 、 ammonium acetate 作用下， 以 乙醚 为溶剂， 反应 11.5h， 生成 diethyl (1-amino-1-phenylethyl)phosphonate
  参考文献：
  名称：

  Novel Coumarin-Containing Aminophosphonatesas Antitumor Agent: Synthesis, Cytotoxicity, DNA-Binding and Apoptosis Evaluation

  摘要：

  合成了一系列含有香豆素结构的α-氨基膦酸酯类新化合物，并评估了它们对体外人结直肠癌（HCT-116）、人鼻咽癌（人KB）和人肺腺癌（MGC-803）细胞系的抗癌活性。与7-羟基-4-甲基香豆素（4-MU）相比，大多数衍生物显示出增强的抗癌活性。化合物8j（二乙基1-（3-（4-甲基-2-氧-2H-色烯-7-基氧）丙酰胺基）-1-苯乙基膦酸酯），对HCT-116细胞系的IC50值为8.68 μM，是其未取代母体化合物的约12倍。机制研究表明，8c、8d、8f和8j通过诱导G1期细胞周期阻滞来实现细胞凋亡。此外，进一步揭示了化合物8j诱导HCT-116细胞凋亡的机制，表明化合物8j通过激活caspase-9和caspase-3引起细胞凋亡，并改变抗凋亡和促凋亡蛋白。DNA结合实验表明，某些衍生物通过嵌插与DNA结合。结果似乎暗示了香豆素和氨基膦酸酯之间存在重要的协同效应，这可能有助于氨基膦酸酯部分的强螯合特性。

  DOI：

  10.3390/molecules200814791

文献信息

• A Novel Catalytic Three-Component Synthesis (Kabachnick-Fields Reaction) of α-Aminophosphonates from Ketones
  作者：Elena D. Matveeva、Nikolay S. Zefirov、Tatyana A. Podrugina、Elena V. Tishkovskaya、Larisa G. Tomilova

  DOI：10.1055/s-2003-42118

  日期：——

  A novel and highly convenient catalytic variant of the synthesis of α-aminophosphonates on basis of the Kabachnik-Fields reaction [three-component reaction of ketones, diethylphosphite and either benzylamine (series a) ofammonium carbonate (series b)] in the presence of tetra-tert-butylphthalocyanines has been developed. This method affords α-aminophosphonates in acceptable yields for various ketones

  基于 Kabachnik-Fields 反应 [酮、亚磷酸二乙酯和碳酸铵（系列 b）的苄胺（系列 b）的三组分反应]合成 α-氨基膦酸酯的一种新型且非常方便的催化变体-叔丁基酞菁已被开发。该方法以可接受的产率为各种酮提供 α-氨基膦酸酯，包括环状酮、空间位阻酮和笼酮。未取代的α-氨基膦酸也从b系列的相应酯中获得。
• Compound, Manufacturing Method Therefor, and Method for Manufacturing Optically Active alpha-Aminophosphonate Derivative
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：US20160145278A1

  公开（公告）日：2016-05-26

  A method for producing a compound represented by General Formula (1), the method including: reacting a compound represented by General Formula (3) and a compound represented by General Formula (4): where R 1 and R 2 each represent aliphatic group which may have substituent, or aromatic group which may have substituent (with the proviso that R 1 and R 2 are different groups), R 3 represents aromatic group which may have substituent, and R 4 represents aliphatic group which may have substituent, or aromatic group which may have substituent, where R 1 and R 2 each represent aliphatic group which may have substituent, or aromatic group which may have substituent (with the proviso that R 1 and R 2 are different groups), and R 3 represents aromatic group which may have substituent, where R 4 represents aliphatic group which may have substituent, or aromatic group which may have substituent.

  一种制备通式（1）所代表化合物的方法，包括：反应通式（3）所代表的化合物和通式（4）所代表的化合物：其中R1和R2分别代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团（前提是R1和R2是不同的基团），R3代表可能具有取代基的芳香族基团，R4代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团，其中R1和R2分别代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团（前提是R1和R2是不同的基团），R3代表可能具有取代基的芳香族基团，R4代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团。
• Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α-Aminophosphonates
  作者：Jiaxiang Lu、Zhenghua Li、Li Deng

  DOI：10.1021/jacs.3c14517

  日期：2024.2.21

  synthetic accessibility of amides render them valuable precursors for the synthesis of diverse nitrogen-containing compounds. Herein, we present a metal-free and streamlined synthetic strategy for the synthesis of quaternary α-aminophosphonates. This approach involves sequential deoxygenative nucleophilic phosphonation and versatile electrophilic alkylation of secondary amides in a one-pot fashion. Notably

  酰胺的广泛存在和合成可及性使其成为合成各种含氮化合物的宝贵前体。在此，我们提出了一种用于合成 α-氨基膦酸季盐的无金属且简化的合成策略。该方法涉及一锅法中仲酰胺的连续脱氧亲核磷酸化和多功能亲电烷基化。值得注意的是，该方法首次实现了仲酰胺与亲核试剂和亲电试剂的直接双官能化，通过简单的衍生化，通过水解产生有价值的游离α-氨基膦酸酯。该协议具有操作简单、功能组广泛兼容性、环境友好以及可扩展到多克数量的优点。
• Coumarin-containing aminophosphonates bridged with chiral side chain: synthesis and influence of chirality on cytotoxicity and DNA binding
  作者：Ya-Jun Li、Man-Yi Ye、Ri-Zhen Huang、Gui-Yang Yao、Ying-Ming Pan、Zhi-Xin Liao、Heng-Shan Wang

  DOI：10.1007/s00044-013-0899-3

  日期：2014.6

  A series of novel coumarin-containing alpha-aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2-bromophenyl)methylphosphonate) was obtained. The in vitro antitumor activities of compound 8a-8g' against human pulmonary carcinoma cell line (A549), human nasopharyngeal carcinoma (human KB), and human lung adenocarcinoma (MGC-803) cell lines were evaluated. Some compounds showed relatively high cytotoxicity. Compared with 8g, 8g' exhibited an improved activity against three tumor cells, which was evidenced by the IC50 that was four- to five-fold lower than those for 8g. The influence of chirality was also observed in DNA-binding assay of 8g and 8g'. 8g' exhibited higher binding constant (1.96 x 10(3) M-1) as compared to 8g (1.69 x 10(3) M-1).
• Medwed'; Kabatschnik, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1954, p. 314,321; engl. Ausg. S. 255, 260
  作者：Medwed'、Kabatschnik

  DOI：——

  日期：——