diethyl 1-(benzyloxycarbonylamino)-1-trifluoromethylbut-3-yne-1-ylphosphonate | 1228473-25-3

• 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 1-(benzyloxycarbonylamino)-1-trifluoromethylbut-3-yne-1-ylphosphonate
• 英文别名: benzyl N-(2-diethoxyphosphoryl-1,1,1-trifluoropent-4-yn-2-yl)carbamate
• CAS: 1228473-25-3
• 化学式: C₁₇H₂₁F₃NO₅P
• 分子量: 407.326
• InChiKey: QGYKRFWXQCZMLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 1-(benzyloxycarbonylamino)-1-trifluoromethylbut-3-yne-1-ylphosphonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， -78.0~80.0 ℃ 、13.33 Pa 条件下， 反应 24.0h， 生成 dimethyl 4-(2-(((benzyloxy)carbonyl)amino)-2-(diethoxyphosphoryl)-3,3,3-trifluoropropyl)phthalate
  参考文献：
  名称：

  Access to Functionalized α-Trifluoromethyl-α-aminophosphonates via Intermolecular Ene–Yne Metathesis

  摘要：

  An efficient approach to a new family of highly functionalized P analogues of alpha-trifluoromethyl-substituted phenylalanine and its homologues using ruthenium-catalyzed intermolecular ene-yne metathesis as a key step of the reaction sequence has been developed. The method includes cross metathesis of alpha-alkynyl-alpha-trifluoromethyl-alpha-aminophosphonates with alkenes under catalysis by second-generation Grubbs carbene complex to afford the corresponding aminophosphonates with 1,3-diene backbone followed by one-pot Diels-Alder reaction-aromatization step.

  DOI：

  10.1055/s-0034-1379229
• 作为产物：
  描述：

  diethyl (N-benzyloxycarbonyl-2,2,2-trifluoroethaneimidoyl)phosphonate 、 allenylmagnesium bromide 在 氯化铵 作用下， 以 乙醚 、 水 为溶剂， 反应 5.0h， 以57%的产率得到diethyl 1-(benzyloxycarbonylamino)-1-trifluoromethylbut-3-yne-1-ylphosphonate
  参考文献：
  名称：

  Synthesis of functionalized α-CF3-α-aminophosphonates via Cu(I)-catalyzed 1,3-dipolar cycloaddition

  摘要：

  A convenient method for the preparation of alpha-CF3-alpha-aminophosphonates bearing alkynyl group at the a-carbon atom has been described. New alkynylphosphonates have been further utilized in the synthesis of functionalized triazole-containing alpha-CF3-alpha-aminophosphonates via copper-catalyzed (3+2)-cycloaddition to different organic azides. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.12.003

文献信息

• Click-chemistry approach to isoxazole-containing α-CF3-substituted α-aminocarboxylates and α-aminophosphonates
  作者：Daria V. Vorobyeva、Natalya M. Karimova、Irina L. Odinets、Gerd-Volker Röschenthaler、Sergey N. Osipov

  DOI：10.1039/c1ob06040f

  日期：——

  A convenient strategy for the synthesis of isoxazole-containing α-CF3-substituted α-aminocarboxylates and α-aminophosphonates have been developed. The method is based on copper-catalyzed 1,3-dipolar cycloaddition of different aromatic nitrile oxides to functionalized acetylenes.

  我们开发了一种合成含异噁唑的δ±-CF3 取代的δ±-氨基羧酸盐和δ±-氨基膦酸盐的简便策略。该方法基于铜催化不同芳香族腈氧化物与官能化乙炔的 1,3-二极环化反应。
• Rh(III)‐Catalyzed C−H Activation/Annulation of Aryl Hydroxamates with CF ₃ ‐Containing <i>α</i> ‐Propargyl <i>α</i> ‐Amino Acid Derivatives
  作者：Daria V. Vorobyeva、Dmitry A. Petropavlovskikh、Ivan A. Godovikov、Sergey E. Nefedov、Sergey N. Osipov

  DOI：10.1002/ejoc.202100040

  日期：2021.3.26

  Novel α‐CF3‐containing isoquinolone derivatives have been synthesized throgh the Rh(III)‐catalyzed C−H activation/annulation of aryl hydroxamates with α‐CF3‐α‐propargyl‐α‐amino carboxylates/phosphonates.

  新颖α-CF 3个含异喹啉酮衍生物已throgh上的Rh（III）催化的合成异羟芳基的C-H活化/环用α-CF 3 -α -炔丙基α-氨基羧酸盐/膦酸盐。
• Ruthenium-catalyzed cyclotrimerization of α-amino-α-propargyl carboxylates and phosphonates with 1,6-diynes: synthesis of α-CF3-containing phenylalanine derivatives and their P-analogs
  作者：M. A. Zotova、T. P. Vasilyeva、S. N. Osipov

  DOI：10.1007/s11172-014-0762-9

  日期：2014.11

  Ruthenium-catalyzed cocyclotrimerization of α-amino-α-propargyl-α-trifluoromethyl carboxylates and phosphonates with functional 1,6-diynes gives the corresponding CF3-containing phenylalanine derivatives and their phosphorus analogs.

  在钌催化下，α-氨基-α-丙炔基-α-三氟甲基羧酸盐和膦酸盐与官能团 1,6- 二炔发生环三聚反应，生成相应的含 CF3 的苯丙氨酸衍生物及其磷类似物。
• Synthesis of CF3-containing α-alkynyl-α-aminophosphonates by Sonogashira cross-coupling reaction
  作者：Maria A. Zotova、Tamara P. Vasilyeva、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1016/j.jfluchem.2011.07.028

  日期：2012.3

  An efficient route to new alpha-CF3-alpha-aminophosphonic acid derivatives bearing an arylalkynyl moiety at the alpha-carbon atom has been developed. The method is based on palladium-catalyzed cross-coupling of the corresponding alpha-propargyl (ethynyl) alpha-aminophosphonates with aryl iodides to afford the aminophosphonic acid derivatives with an internal triple bond that is suitable for further modifications. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence
  作者：Daria V. Vorobyeva、Nadezhda V. Sokolova、Valentine G. Nenajdenko、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1016/j.tet.2011.11.037

  日期：2012.1

  A convenient synthetic pathway to novel functionalized tetrapeptides containing the 1,2,3-triazole moiety is described. The target molecules were obtained by the reaction of fluorinated alpha-amino acids or alpha-aminophosphonates with azidopeptides via Cu(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). The synthesized tetrapeptides may find important applications in biomedical chemistry as potential drugs. (C) 2011 Elsevier Ltd. All rights reserved.