dimethyl ((tritylamino)methyl)phosphonate | 120060-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: dimethyl ((tritylamino)methyl)phosphonate
• 英文别名: N-(dimethoxyphosphorylmethyl)-1,1,1-triphenylmethanamine
• CAS: 120060-80-2
• 化学式: C₂₂H₂₄NO₃P
• 分子量: 381.411
• InChiKey: BJMUJAXLDYOOHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl ((tritylamino)methyl)phosphonate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 dimethyl aminomethylphosphonate hydrochloride
  参考文献：
  名称：

  Tritylamine (Triphenylmethylamine) in Organic Synthesis; I. The Synthesis ofN-(Triphenylmethyl)alkanimines, 1-(Triphenylmethylamino)alkylphosphonic Esters, and 1-Aminoalkylphosphonic Acids and Esters

  摘要：

  三甲胺（氨的合成类似物）在制备未知的N-(三苯甲基)烷基亚胺中的应用已被描述。这些亚胺是制备1-(三苯甲基氨基)烷基膦酸酯的便利合成子，后者可作为合成1-氨基烷基膦酸及其衍生物的起始材料。

  DOI：

  10.1055/s-1988-27576
• 作为产物：
  描述：

  三苯甲胺 以 苯 为溶剂， 反应 24.0h， 生成 dimethyl ((tritylamino)methyl)phosphonate
  参考文献：
  名称：

  Tritylamine (Triphenylmethylamine) in Organic Synthesis; I. The Synthesis ofN-(Triphenylmethyl)alkanimines, 1-(Triphenylmethylamino)alkylphosphonic Esters, and 1-Aminoalkylphosphonic Acids and Esters

  摘要：

  三甲胺（氨的合成类似物）在制备未知的N-(三苯甲基)烷基亚胺中的应用已被描述。这些亚胺是制备1-(三苯甲基氨基)烷基膦酸酯的便利合成子，后者可作为合成1-氨基烷基膦酸及其衍生物的起始材料。

  DOI：

  10.1055/s-1988-27576

文献信息

• Synthesis and Plant Growth Regulating Activity of New Triazolo- and Pyrazolopyrimidine Derivatives Of Aminomethyl, Aminoalkyloxymethyl Dimethylphosphine Oxides and (Aminomethane)Phosphonic Acid Esters
  作者：Elena Stanoeva、Sabi Varbanov、Vera Alexieva、Iskren Sergiev、Vesselina Vasileva、Marieta Rashkova、Angelina Georgieva

  DOI：10.1080/10426500008076331

  日期：2000.2

  Abstract New triazolo[4,5-d]pyrimidine and pyrazolo[3,4-d]pyrimidine derivatives of aminomethyl-and aminomethyloxymethyl dimethylphosphine oxides 8–14 as well as of esters of (aminomethane) phosphonic acid 18–20 were synthesized. The structure of the compounds prepared was confirmed by means of elemend analysis, IR, 1H- and 31P(1H)-NMR spectroscopy. Tertiary phosphine oxides 8, 9 and 12 as well as

  摘要 合成了氨甲基和氨甲氧基甲基二甲基膦氧化物 8-14 以及（氨基甲烷）膦酸酯 18-20 的新三唑并[4,5-d]嘧啶和吡唑并[3,4-d]嘧啶衍生物。制备的化合物的结构通过元素分析、IR、1H-和31P(1H)-NMR光谱证实。叔氧化膦 8、9 和 12 以及膦酸酯 20 显示出除草和植物生长调节活性。
• Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
  作者：Adrián López-Francés、Xabier del Corte、Edorta Martínez de Marigorta、Francisco Palacios、Javier Vicario

  DOI：10.3390/molecules26061654

  日期：——

  An Ugi three-component reaction using preformed α-phosphorated N-tosyl ketimines with different isocyanides in the presence of a carboxylic acid affords tetrasubstituted α-aminophosphonates. Due to the high steric hindrance, the expected acylated amines undergo a spontaneous elimination of the acyl group. The reaction is applicable to α-aryl ketimines bearing a number of substituents and several isocyanides. In addition, the densely substituted α-aminophosphonate substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell line A549 (carcinomic human alveolar basal epithelial cell).

  使用预制的α-磷酸化N-对甲苯磺酰基亚胺与不同异氰酸酯在存在羧酸的情况下进行的Ugi三组分反应可得到四取代的α-氨基膦酸酯。由于高位阻效应，预期的酰化胺会发生酰基的自发消除。该反应适用于带有多个取代基和几种异氰酸酯的α-芳基酮亚胺。此外，密集取代的α-氨基膦酸酯底物在体外显示出细胞毒性，抑制了癌症人类肿瘤细胞系A549（癌症人类肺泡基底上皮细胞）的生长。
• Asymmetric Synthesis of α‐Amino Phosphonic Acids using Stable Imino Phosphonate as a Universal Precursor
  作者：Tsubasa Inokuma、Takuya Sakakibara、Takatoshi Someno、Kana Masui、Akira Shigenaga、Akira Otaka、Ken‐ichi Yamada

  DOI：10.1002/chem.201903572

  日期：2019.10.28

  A practical method for synthesizing chiral α-amino phosphonic acid derivatives was developed. Readily available and stable N-o-nitrophenylsulfenyl (Nps) imino phosphonate was utilized as a substrate for a highly enantioselective Friedel-Crafts-type addition of indole or pyrrole nucleophiles catalyzed by chiral phosphoric acid. The resulting adduct was easily converted into N-9-fluorenylmethyloxycarbonyl

  开发了一种合成手性α-氨基膦酸衍生物的实用方法。现成的稳定的No-nitrophenylsulfenyl（Nps）亚氨基膦酸酯用作手性磷酸催化的吲哚或吡咯亲核试剂的高对映选择性Friedel-Crafts型加成物的底物。所得的加合物易于转化为N-9-芴基甲氧基羰基（Fmoc）氨基膦酸，其可用于合成含有氨基膦酸的肽。
• Synthesis of novel antiproliferative hybrid bis-(3-indolyl)methane phosphonate derivatives
  作者：Aitor Maestro、Endika Martín-Encinas、Concepción Alonso、Edorta Martinez de Marigorta、Gloria Rubiales、Javier Vicario、Francisco Palacios

  DOI：10.1016/j.ejmech.2018.09.011

  日期：2018.10

  An efficient synthetic methodology for the preparation of phosphorus substituted bis-(3-indolyl)methane through a double nucleophilic addition of indole derivatives to an in situ generated α-iminophosphonate is reported. In addition, bis-(3-indolyl)methane substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines A549 (carcinomic human alveolar basal epithelial

  报道了通过将吲哚衍生物双亲核加成到原位产生的α-亚氨基膦酸酯中来制备磷取代的双-（3-吲哚基）甲烷的有效合成方法。另外，双-（3-吲哚基）甲烷底物显示出体外细胞毒性，抑制了癌人类肿瘤细胞系A549（癌性人类肺泡基底上皮细胞）和SKOV03（人类卵巢癌）的生长。
• Boduszek; Soroka, Polish Journal of Chemistry, 2002, vol. 76, # 8, p. 1105 - 1111
  作者：Boduszek、Soroka

  DOI：——

  日期：——