2-Diethoxyphosphoryl-2-thiophen-2-ylacetonitrile | 130138-53-3

• 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: 2-Diethoxyphosphoryl-2-thiophen-2-ylacetonitrile
• CAS: 130138-53-3
• 化学式: C₁₀H₁₄NO₃PS
• 分子量: 259.266
• InChiKey: RBWKRUPENANIPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  140 °C(Press: 0.8 Torr)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 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：
  87.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Diethoxyphosphoryl-2-thiophen-2-ylacetonitrile 在 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (Z)-3-[3-(3-Amino-5-ethyl-6-methyl-2-oxo-1,2-dihydro-pyridine-4-carbonyl)-phenyl]-2-thiophen-2-yl-acrylonitrile
  参考文献：
  名称：

  4-Benzyl- and 4-Benzoyl-3-dimethylaminopyridin-2(1H)-ones, a New Family of Potent Anti-HIV Agents:  Optimization and in Vitro Evaluation against Clinically Important HIV Mutant Strains

  摘要：

  The 4-benzyl and 4-benzoyl-3-dimethylaminopyridinones 13 and 14 are representatives of a new class of highly potent non nucleoside type inhibitors of HIV-1 reverse transcriptase. To conduct SAR studies on these two lead compounds, 102 new analogues were prepared. Thirty-three compounds displayed nanomolar range activity in vitro against wild-type HIV-1, and among these, 18 were active against the 103N, Y181C, and Y188L mutant strains with IC50 values inferior to 1 muM. Evaluation of this group of analogues against an additional eight single [100I, 101E, 106A, 138K, 179E, 190A, 190S, 227C] and four double HIV mutant strains [100I + 103N, 101E + 103N, 103N + 181C, and 227L + 106A], which are often present in HIV infected patients, permitted the selection of eight compounds, 17x, 18b, 18c, 18f, 18g, 27, 30, and 42, which are globally more active than the lead molecules 13/14, emivirine and the currently used NNRTI, nevirapine. Further comparison of the 3'-CN-substituted benzoylpyridinone compound 18c, and the corresponding 3'-acrylonitrile-substituted analogue 30, to efavirenz, the reference molecule in anti-HIV therapy today, revealed that the pyridinone analogues displayed a superior inhibition profile in the in vitro cellular assay system. These results form a solid basis for continued optimization of the pyridinone series.

  DOI：

  10.1021/jm0407658
• 作为产物：
  描述：

  2-溴噻吩 、 氰甲基磷酸二乙酯 在 四(三苯基膦)钯 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以59%的产率得到2-Diethoxyphosphoryl-2-thiophen-2-ylacetonitrile
  参考文献：
  名称：

  Palladium-catalyzed condensation of aryl halides with phenylsulfonylacetonitrile and diethyl cyanomethylphosphonate.

  摘要：

  用钯(0)催化的芳香卤化物与苯基磺酰乙腈和二乙基氰基甲基膦酸钠在二甲氧基乙烷中缩合，得到相应的α-苯基磺酰芳烃乙腈和二乙基芳氰基甲基膦酸酯，产率良好。α-苯基磺酰芳烃乙腈可以用锌轻松去磺化生成芳烃乙腈，而芳氰基甲基膦酸酯通过霍纳-艾蒙斯反应转化为烷基亚烯芳烃乙腈。

  DOI：

  10.1248/cpb.38.1513

文献信息

• Asymmetric Electrophilic Fluorination of α-Cyanoalkylphosphonates ­Catalyzed by Chiral Palladium Complexes
  作者：Dae Kim、Young Kang、Min Cho、Sun Kim

  DOI：10.1055/s-2007-977436

  日期：2007.4

  The catalytic enantioselective fluorination of α-cyano­alkylphosphonates catalyzed by chiral palladium complexes was examined. Treatment of α-cyanoalkylphosphonates with N-fluoro­benzenesulfonimide as the electrophilic fluorinating reagent under mild reaction conditions afforded the corresponding α-fluorinated α-cyanoalkylphosphonates in excellent yields with high enantiomeric excesses (80-91%).

  研究了手性钯配合物催化的α-氰基烷基膦酸酯的催化对映选择性氟化反应。在温和反应条件下，使用N-氟苯磺酰亚胺作为电亲和氟化试剂处理α-氰基烷基膦酸酯，获得了相应的α-氟化α-氰基烷基膦酸酯，产率良好且对映体过量高（80-91%）。
• SAKAMOTO, TAKAO;KATOH, EISAKU;KONDO, YOSHINORI;YAMANAKA, HIROSHI, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1513-1517
  作者：SAKAMOTO, TAKAO、KATOH, EISAKU、KONDO, YOSHINORI、YAMANAKA, HIROSHI

  DOI：——

  日期：——
• 4-Benzyl- and 4-Benzoyl-3-dimethylaminopyridin-2(1<i>H</i>)-ones, a New Family of Potent Anti-HIV Agents:  Optimization and in Vitro Evaluation against Clinically Important HIV Mutant Strains
  作者：Abdellah Benjahad、Karine Courté、Jérôme Guillemont、Dominique Mabire、Sophie Coupa、Alain Poncelet、Imre Csoka、Koen Andries、Rudi Pauwels、Marie-Pierre de Béthune、Claude Monneret、Emile Bisagni、Chi Hung Nguyen、David S. Grierson

  DOI：10.1021/jm0407658

  日期：2004.10.1

  The 4-benzyl and 4-benzoyl-3-dimethylaminopyridinones 13 and 14 are representatives of a new class of highly potent non nucleoside type inhibitors of HIV-1 reverse transcriptase. To conduct SAR studies on these two lead compounds, 102 new analogues were prepared. Thirty-three compounds displayed nanomolar range activity in vitro against wild-type HIV-1, and among these, 18 were active against the 103N, Y181C, and Y188L mutant strains with IC50 values inferior to 1 muM. Evaluation of this group of analogues against an additional eight single [100I, 101E, 106A, 138K, 179E, 190A, 190S, 227C] and four double HIV mutant strains [100I + 103N, 101E + 103N, 103N + 181C, and 227L + 106A], which are often present in HIV infected patients, permitted the selection of eight compounds, 17x, 18b, 18c, 18f, 18g, 27, 30, and 42, which are globally more active than the lead molecules 13/14, emivirine and the currently used NNRTI, nevirapine. Further comparison of the 3'-CN-substituted benzoylpyridinone compound 18c, and the corresponding 3'-acrylonitrile-substituted analogue 30, to efavirenz, the reference molecule in anti-HIV therapy today, revealed that the pyridinone analogues displayed a superior inhibition profile in the in vitro cellular assay system. These results form a solid basis for continued optimization of the pyridinone series.
• Palladium-catalyzed condensation of aryl halides with phenylsulfonylacetonitrile and diethyl cyanomethylphosphonate.
  作者：Takao SAKAMOTO、Eisaku KATOH、Yoshinori KONDO、Hiroshi YAMANAKA

  DOI：10.1248/cpb.38.1513

  日期：——

  The palladium(0)-catalyzed condensation of aryl halides with the sodium salts of phenylsulfonylacetonitrile and diethyl cyanomethylphonate in dimethoxyethane gave the corresponding α-phenylsulfonylareneacetonitriles and diethyl arylcyanomethylphosphonates in good yields.The α-phenylsulfonylareneacetonitriles were easily desulfonylated with zinc to give the areneacetonitriles, and the arylcyanomethylphonates were converted to the alkylideneareneacetonitriles by means of the Horner-Emmons reaction.

  用钯(0)催化的芳香卤化物与苯基磺酰乙腈和二乙基氰基甲基膦酸钠在二甲氧基乙烷中缩合，得到相应的α-苯基磺酰芳烃乙腈和二乙基芳氰基甲基膦酸酯，产率良好。α-苯基磺酰芳烃乙腈可以用锌轻松去磺化生成芳烃乙腈，而芳氰基甲基膦酸酯通过霍纳-艾蒙斯反应转化为烷基亚烯芳烃乙腈。