N-[二乙氧基磷酰基(苯基)甲基]苯甲酰胺 | 123978-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[二乙氧基磷酰基(苯基)甲基]苯甲酰胺
• 英文名称: diethyl N-benzoyl-α-aminobenzyl-phosphonate
• 英文别名: diethyl (N-benzoyl)aminophenylmethyl phosphonate；diethyl (phenyl)benzamidomethylphosphonate；(α-benzoylamino-benzyl)-phosphonic acid diethyl ester；(α-Benzoylamino-benzyl)-phosphonsaeure-diaethylester；Diethyl [benzamido(phenyl)methyl]phosphonate；N-[diethoxyphosphoryl(phenyl)methyl]benzamide
• CAS: 123978-87-0
• 化学式: C₁₈H₂₂NO₄P
• 分子量: 347.351
• InChiKey: WSFJEDKBRTZTPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[二乙氧基磷酰基(苯基)甲基]苯甲酰胺 在 盐酸 作用下， 反应 16.0h， 以85.3%的产率得到(Amino-phenyl-methyl)-phosphonic acid; hydrochloride
  参考文献：
  名称：

  Phosphoranaloge von Aminosäuren II¹. Synthese von α-Aminophosphonsäuren und α-Aminophosphinsäuren, ausgehend von den entsprechendenN-Acylimino-Derivaten

  摘要：

  通过相应的 N-酰亚胺衍生物合成δ-氨基膦酸和δ-氨基膦酸酰亚胺甲基膦酸和酰亚胺甲基膦酸酯通常由相应的酰亚胺（溴）甲基化合物原位生成，与高阶混合铜酸盐反应，水解后分别生成 C-取代的氨基甲基膦酸和氨基甲基膦酸。

  DOI：

  10.1055/s-1989-27162
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 N-[二乙氧基磷酰基(苯基)甲基]苯甲酰胺
  参考文献：
  名称：

  Medwed'; Kabatschnik, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1955, p. 1043,1046; engl. Ausg. S. 957, 959

  摘要：

  DOI：

文献信息

• Phosphatase inhibitors—III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase
  作者：Scott A. Beers、Charles F. Schwender、Deborah A. Loughney、Elizabeth Malloy、Keith Demarest、Jerold Jordan

  DOI：10.1016/0968-0896(96)00186-1

  日期：1996.10

  phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the alpha-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution of the alpha-amino group led to great reductions in potency.

  对人前列腺酸磷酸酶的一系列苄基膦酸抑制剂的结构要求的进一步研究导致了一系列高效的α-氨基苄基膦酸。IC50 = 4 nM的α-苄基氨基苄基膦酸的效能比碳类似物α-苯乙基提高了3500倍。增强的效力可能是由于四种有利相互作用的组合，包括与磷酸盐结合区的相互作用，苄氨基和苯基膦酸的疏水部分的存在以及膦酸酯和α-之间的内部盐桥产生的刚性构象异构体。氨基。
• Palladium-catalysed aminocarbonylation of iodoarenes and iodoalkenes with aminophosphonate as N-nucleophile
  作者：Attila Takács、Andrea Petz、László Kollár

  DOI：10.1016/j.tet.2008.06.096

  日期：2008.9

  The high-yielding synthesis of novel N-acyl phosphonates with unprecedented structure was carried out by a homogeneous carbonylation reaction under mild reaction conditions. The palladium-catalysed aminocarbonylation of iodoalkenes (1-iodo-cyclohexene, 1-iodo-4-tert-butyl-cyclohexene, 1-iodo-2-methyl-cyclohexene and α-iodostyrene) with diethyl α-aminobenzyl-phosphonate as N-nucleophile resulted in

  在温和的反应条件下，通过均相的羰基化反应进行了具有空前结构的新型N-酰基膦酸酯的高产率合成。iodoalkenes（1-碘环己烯，1-碘-4-的钯催化氨基羰基化叔丁基环己烯，1-碘-2-甲基-环己烯和α-碘苯乙烯）用二α氨基苄基-膦酸酯作为ñ -亲核试剂导致羧酰胺的排他性形成。与碘代芳香族化合物（碘代苯，2-碘代噻吩）进行的相同反应分别提供了高产率的相应羧酰胺和作为副产物的某些2-酮-羧酰胺，分别由于插入了一次和两次一氧化碳。
• 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.
• SCHRADER, THOMAS;STEGLICH, WOLFGAN, SYNTHESIS,(1989) N, C. 97-101
  作者：SCHRADER, THOMAS、STEGLICH, WOLFGAN

  DOI：——

  日期：——
• Medwed'; Kabatschnik, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1955, p. 1043,1046; engl. Ausg. S. 957, 959
  作者：Medwed'、Kabatschnik

  DOI：——

  日期：——