diethyl (benzylamino)(p-tolyl)methylphosphonate | 135473-50-6

• 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: diethyl (benzylamino)(p-tolyl)methylphosphonate
• 英文别名: N-benzyl-1-diethoxyphosphoryl-1-(4-methylphenyl)methanamine
• CAS: 135473-50-6
• 化学式: C₁₉H₂₆NO₃P
• 分子量: 347.394
• InChiKey: YLFRGKLDUOANHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (benzylamino)(p-tolyl)methylphosphonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0~25.0 ℃ 、101.32 kPa 条件下， 反应 30.0h， 以78.4%的产率得到膦酸,[氨基(4-甲基苯基)甲基]-,二乙基酯
  参考文献：
  名称：

  Maier, Ludwig; Diel, Peter J., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 57, # 1/2, p. 57 - 64

  摘要：

  DOI：
• 作为产物：
  描述：

  苄胺 在 三氟化硼乙醚 、 sodium sulfate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 diethyl (benzylamino)(p-tolyl)methylphosphonate
  参考文献：
  名称：

  Maier, Ludwig; Diel, Peter J., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 57, # 1/2, p. 57 - 64

  摘要：

  DOI：

文献信息

• A facile and highly efficient route to α-amino phosphonates via three-component reactions catalyzed by Mg(ClO₄)₂or molecular iodine
  作者：Jie Wu、Wei Sun、Hong-Guang Xia、Xiaoyu Sun

  DOI：10.1039/b602536f

  日期：——

  Three-component reactions of aldehydes, amines, and diethyl phosphite catalyzed by Mg(ClO4)2 or molecular iodine afforded the corresponding α-amino phosphonates in excellent yields under mild reaction conditions.

  在 Mg(ClO4)2 或分子碘的催化下，醛、胺和亚磷酸二乙酯发生三组分反应，在温和的反应条件下以极好的收率得到了相应的δ-氨基膦酸盐。
• New <i>N</i>-acyl- as well as <i>N</i>-phosphonoylmethyl- and <i>N</i>-phosphinoylmethyl-α-amino-benzylphosphonates by acylation and a tandem Kabachnik–Fields protocol
  作者：Petra Regina Varga、Konstantin Karaghiosoff、Éva Viktória Sári、András Simon、László Hegedűs、László Drahos、György Keglevich

  DOI：10.1039/d3ob00010a

  日期：——

  approach, in a second Kabachnik–Fields condensation by reaction with formaldehyde and dialkyl phosphites or secondary phosphine oxides to afford novel N-phosphonoylmethyl- and N-phosphinoylmethyl-α-amino-benzylphosphonates. The structure of the new products was confirmed by two-dimensional NMR spectroscopy. A symmetrical bis derivative was prepared in a diastereoselective manner. A related tris(phosphonoylmethyl)amine

  通过 Kabachnik–Fields 反应获得的 α-苄基氨基-和 α-氨基-苄基膦酸二乙酯是合成其他衍生物的有用中间体。α-氨基膦酸酯与酰氯的酰化导致在两种构象异构体的动态平衡下存在相应的N-酰基物质。从广泛的 NMR 信号来看，空间上最拥挤的N -苯甲酰基 - N-苄基衍生物在 26 °C 时绕 N-C 轴向酰基碳原子旋转受阻。-10 °C 的低温 NMR 测量显示存在两种不同的旋转异构体，这些旋转异构体已被表征。制备的其他酰化 α-氨基-苄基膦酸酯显示旋转受阻较小。NH-丙酰基物质的单晶 X 射线衍射显示二聚体，其中两个分子通过稀有的分子间 P O⋯HN 键结合在一起。另一方面，采用磷酸-曼尼希反应制备的取代α-苄基氨基-苄基膦酸酯作为一种新方法，通过与甲醛和二烷基亚磷酸酯或仲氧化膦反应，在第二次卡巴尼克-菲尔兹缩合中得到新的N-膦酰基甲基-和N-膦酰甲基-α-氨基-苄基膦酸酯。新
• Diversity-oriented synthesis of α-aminophosphonates: A new class of potential anticancer agents
  作者：Asish K. Bhattacharya、Dnyaneshwar S. Raut、Kalpeshkumar C. Rana、Innaiah K. Polanki、Mohd Sajid Khan、Sana Iram

  DOI：10.1016/j.ejmech.2013.05.036

  日期：2013.8

  A small library of structurally diverse alpha-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized alpha-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized alpha-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC50 value of 4 mu M. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.