N-[[oxido(dipropoxy)phosphaniumyl]-phenylmethyl]-1-phenylmethanimine | 1038997-68-0

• 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: N-[[oxido(dipropoxy)phosphaniumyl]-phenylmethyl]-1-phenylmethanimine
• CAS: 1038997-68-0
• 化学式: C₂₀H₂₆NO₃P
• 分子量: 359.405
• InChiKey: DHORVJPCIDBFBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  53.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[[oxido(dipropoxy)phosphaniumyl]-phenylmethyl]-1-phenylmethanimine 在 吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 O,O'-dipropyl {[2-(2,4-dichlorophenoxy)acetamido](phenyl)methyl}phosphonate
  参考文献：
  名称：

  Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates

  摘要：

  A series of O,O'-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates was synthesized and their cytotoxic activities were tested against various human tumor cell lines. Some compounds (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. Especially, compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells with IC50 7.1 and 11.4 mu M, respectively. Their inhibitory activities against KB and CNE2 cells were even higher than that of fluorouracil. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.014
• 作为产物：
  描述：

  苯甲醛 在 ammonium hydroxide 作用下， 生成 N-[[oxido(dipropoxy)phosphaniumyl]-phenylmethyl]-1-phenylmethanimine
  参考文献：
  名称：

  含α-氨基膦酸酯部分的新型吡唑酰胺的合成及抗病毒活性

  摘要：

  合成了一系列新颖的吡唑酰胺J1，J2，J3，J4，J5，J6，J7，J8，J9，J10，J11，J12，J13，J14，J15，含有α-氨基膦酸酯部分，并随后通过光谱（IR ，1 H‐，13 C‐，31 P‐和19 F‐NMR）数据和元素分析。J1的外消旋体样品在两个固定的基于多糖的手性固定相（Chiralpak IA和Chiralpak IC）上，在正相条件下将其进一步分离为对映体。合成的化合物在生物测定中显示出一定程度的抗病毒活性。标题化合物（J3，J10和J12）在0.5 mg / mL的浓度下对烟草花叶病毒显示出一定的治愈活性（分别为39.9％，41.8％，50.1％）。杂环化学杂志，00，00（2011）。

  DOI：

  10.1002/jhet.591

文献信息

• Synthesis and antiviral activity of novel pyrazole amides containing α-aminophosphonate moiety
  作者：Lintao Wu、Baoan Song、Pinaki S. Bhadury、Song Yang、Deyu Hu、Linhong Jin

  DOI：10.1002/jhet.591

  日期：2011.3

  A series of novel pyrazole amides J1, J2, J3, J4, J5, J6, J7, J8, J9, J10, J11, J12, J13, J14, J15 containing an α‐aminophosphonate moiety were synthesized and subsequently characterized by spectral (IR, 1H‐, 13C‐, 31P‐, and 19F‐NMR) data and elemental analysis. The racemic sample of J1 was further separated into its enantiomers under normal‐phase condition on two immobilized polysaccharide‐based chiral

  合成了一系列新颖的吡唑酰胺J1，J2，J3，J4，J5，J6，J7，J8，J9，J10，J11，J12，J13，J14，J15，含有α-氨基膦酸酯部分，并随后通过光谱（IR ，1 H‐，13 C‐，31 P‐和19 F‐NMR）数据和元素分析。J1的外消旋体样品在两个固定的基于多糖的手性固定相（Chiralpak IA和Chiralpak IC）上，在正相条件下将其进一步分离为对映体。合成的化合物在生物测定中显示出一定程度的抗病毒活性。标题化合物（J3，J10和J12）在0.5 mg / mL的浓度下对烟草花叶病毒显示出一定的治愈活性（分别为39.9％，41.8％，50.1％）。杂环化学杂志，00，00（2011）。
• Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety
  作者：Xuan Yang、BaoAn Song、LinHong Jin、Xue Wei、S. Pinaki Bhadury、XiangYang Li、Song Yang、DeYu Hu

  DOI：10.1007/s11426-010-4179-5

  日期：2011.1

  and substituted isothiocyanates (9a–d), chiral bis-thiourea derivatives containing α-aminophosphonate moiety 10a–l were prepared and completely characterized by elemental analysis, physical and spectral (IR, 1H NMR, 13C NMR, 31P NMR) data. The results of bioassay revealed that compounds 10a and 10e possessed appreciable curative bioactivities on cucumber mosaic virus (CMV) at 0.5 mg/mL in vivo (inhibitory

  从1开始- （（1 - [R，2 - [R）-2-氨基环己基）-3-取代的硫脲（3A-C ）和取代的异硫氰酸酯（图9a-d ），手性双-硫脲的含α-氨基膦基团的衍生物10A-1是制备并通过元素分析，物理和光谱（IR，1 H NMR，13 C NMR，31 P NMR）数据完全表征。生物测定的结果表明，化合物10a和10e在体内对黄瓜花叶病毒（CMV）具有0.5 mg / mL的显着治愈性生物活性。（抑制率分别为60.3％，64.8％）和烟草花叶病毒（TMV）在体内浓度为0.5 mg / mL （抑制率分别为50.3％，50.8％），与标准参考文献显示的值（58.7％）相近）和市售产品宁南霉素（56.3％）。手性化合物10e显示出比宁南霉素（EC 50 = 0.201mg / mL）更强的抗CMV抗病毒活性（EC 50 = 0.149 mg / mL）。
• Synthesis and Antiviral Activities of Chiral Thiourea Derivatives Containing an α-Aminophosphonate Moiety
  作者：Mei-Hang Chen、Zhuo Chen、Bao-An Song、Pinaki S. Bhadury、Song Yang、Xue-Jian Cai、De-Yu Hu、Wei Xue、Song Zeng

  DOI：10.1021/jf803215t

  日期：2009.2.25

  revealed them as antivirally active. It was found that title compounds 8g, 8e, 8k, and 8m had the same curative effects of TMV (inhibitory rate = 54.8, 50.5, 50.4, and 50.4%, respectively) as the commercial product Ningnanmycin (56.2%). This would appear to be the first report of the synthesis and antiviral activity of chiral thiourea derivatives containing an α-aminophosphonate moiety.

  从苯甲醛1开始，以六个步骤合成标题化合物8。苯甲醛1与氢氧化铵反应，然后将亚胺用亚磷酸二烷基酯3处理，得到N-（芳基亚甲基）-1-氨基-1-芳基二膦酸二烷基酯4。然后将膦酸酯4轻松水解，得到1-氨基-1-芳基-甲基膦酸二烷基酯6，将其用三乙胺，二硫化碳和氯氧化磷处理后得到7。然后通过7的反应制备目标化合物8与取代的手性胺。通过光谱数据（IR，1 H，13 C和31 P NMR，以及元素分析）清楚地验证了结构。这些化合物的生物测定表明它们具有抗病毒活性。发现标题化合物8g，8e，8k和8m具有与市售产品宁南霉素（56.2％）相同的TMV疗效（抑制率分别为54.8、50.5、50.4和50.4％）。这似乎是关于含有α-氨基膦酸酯部分的手性硫脲衍生物的合成和抗病毒活性的首次报道。
• Synthesis and Antiviral Activities of Cyanoacrylate Derivatives Containing an α-Aminophosphonate Moiety
  作者：Ning Long、Xue-Jian Cai、Bao-An Song、Song Yang、Zhuo Chen、Pinaki S. Bhadury、De-Yu Hu、Lin-Hong Jin、Wei Xue

  DOI：10.1021/jf800405m

  日期：2008.7.1

  Target compounds 8 were obtained by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylate or cyarylamide (7a-7e) and (alpha-aminobenzylphosphonate (5a-5e) under reflux condition using ethanol as solvent. Their structures were clearly verified by spectroscopic data (IR and (1)H, (13)C, and (31)P NMR) and elemental analysis. These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 8d and 8e had the same inactivation effect against tobacco mosaic virus (EC(50) = 55.5 and 55.3 mu g/mL) as the commercial product ningnanmycin (EC(50) = 50.9 mu g/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of cyanoacrylate derivatives containing an alpha-aminophosphonate moiety.
• Synthesis and Antiviral Activities of Amide Derivatives Containing the α-Aminophosphonate Moiety
  作者：De-Yu Hu、Qiong-Qiong Wan、Song Yang、Bao-An Song、Pinaki S. Bhadury、Lin-Hong Jin、Kai Yan、Fang Liu、Zhuo Chen、Wei Xue

  DOI：10.1021/jf072394k

  日期：2008.2

  Starting from (substituted-)benzaldehydes, the title compounds 6 were synthesized through five step reactions. Benzaldehydes were treated with ammonium hydroxide, followed by dialkyl phosphite, to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates (3). Phosphonates 3 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 5. Target compounds 6 were then obtained by the reaction of 5 and substituted benzoic or cinnamic acid. Their structures were clearly verified by spectroscopic data (IR, H-1, C-13, and P-31 NMR, and elemental analysis). These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 6g, 61,,and 6n had the same inactivation effect of TMV (EC50 = 54.8, 60.0, and 65.2 mu g/mL, respectively) as commercial product Ningnanmycin (EC50 = 55.6 mu g/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of amide derivatives containing an alpha-aminophosphonate moiety.