diethyl (5-phenyl-1,3,4-oxadiazol-2-yl)methylphosphonate | 52172-49-3

• 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: diethyl (5-phenyl-1,3,4-oxadiazol-2-yl)methylphosphonate
• 英文别名: Diethyl [(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]phosphonate；2-(diethoxyphosphorylmethyl)-5-phenyl-1,3,4-oxadiazole
• CAS: 52172-49-3
• 化学式: C₁₃H₁₇N₂O₄P
• 分子量: 296.263
• InChiKey: BZZXGUWTUHHMFG-UHFFFAOYSA-N

物化性质

• 沸点：
  432.6±47.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲亚胺酸乙酯 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 36.0h， 生成 diethyl (5-phenyl-1,3,4-oxadiazol-2-yl)methylphosphonate
  参考文献：
  名称：

  Synthese Originale de 5-Aryl (ou 5-benzyl)-2[(1-Diethoxyphosphonyl)methyl]-1,3,4-oxadiazoles par Action du Phosphonomethylhydrazide sur les Imidates N-Acyles

  摘要：

  The phosphonomethylhydrazide 2a reacts with N-acylated imidates 3a-d to give the corresponding 5-aryl (or 5-benzyl)-2-[(1-diethoxyphosphonyl)methyl]-1,3,4-oxadiazoles 4a-d after the elimination of ethanamide 5. Compounds 2a-e are prepared by the action of triethyl phosphonoacetate 1 with hydrazine and its derivatives. The structures of 1,3,4-oxadiazoles 4a-d and hydrazides 2a-e have been unequivocally confirmed by means of IR, H-1, C-13, P-31 NMR and mass spectrometry.

  DOI：

  10.1080/10426500600695047

文献信息

• HETEROCYCLIC M-GLU5 ANTAGONISTS
  申请人：Leonardi Amedeo

  公开号：US20120028931A1

  公开（公告）日：2012-02-02

  Compounds I (R 1 is an optionally substituted C 1 -C 13 heteromonocyclic, heterobicyclic or heterotricyclic group containing from 1 to 5 heteroatoms selected from N, O and S; R 2 is H, an optionally substituted monocyclic aromatic group, or a C 1 -C 5 heteroaromatic group containing from 1 to 4 heteroatoms selected from N, O and S; R 3 is an optionally substituted C 1 -C 13 heteromonocyclic, heterobicyclic or heterotricyclic group containing from 1 to 5 heteroatoms selected from N, O and S; an optionally substituted mono-, bi- or tricyclic C 6 -C 14 aryl group, an optionally substituted C 3 -C 6 cycloalkyl group, or an optionally substituted C 3 -C 6 cycloalkenyl group; each R 4 , independently for each position capable of substitution, is H or C 1 -C 6 alkyl; R 5 is H, halogen or C 1 -C 6 alkyl; m is 0, 1 or 2; n is 0, 1 or 2; p is 0, 1, 2, 3, 4, 5, or 6; and is an optional double bond) and their enantiomers, diastereomers, N-oxides and pharmaceutically acceptable salts, and pharmaceutical compositions containing them, are useful for the treatment of neuromuscular dysfunction of the lower urinary tract and also for the treatment of gastrooesophageal reflux disease; anxiety disorder; abuse, substance dependence and substance withdrawal disorders; neuropathic pain disorder, migraine and fragile X syndrome disorders.

  化合物I（其中R1是可选取代的C1-C13杂环单环、杂环双环或杂环三环基团，包含1-5个从N、O和S中选取的杂原子；R2是H、可选取代的单环芳香基团，或包含1-4个从N、O和S中选取的杂原子的C1-C5杂环芳香基团；R3是可选取代的C1-C13杂环单环、杂环双环或杂环三环基团，包含1-5个从N、O和S中选取的杂原子；可选取代的单环、双环或三环C6-C14芳基基团，可选取代的C3-C6环烷基基团或可选取代的C3-C6环烯基基团；每个R4，在可取代的每个位置上，独立地是H或C1-C6烷基；R5是H、卤素或C1-C6烷基；m为0、1或2；n为0、1或2；p为0、1、2、3、4、5或6；并且是可选的双键），它们的对映异构体、顺反异构体、N-氧化物和药学上可接受的盐，以及含有它们的制药组合物，对于治疗下泌尿道神经肌肉功能障碍和胃食管反流病，焦虑症、滥用、物质依赖和物质戒断障碍，神经病性疼痛障碍、偏头痛和脆性X综合症障碍有用。
• Synthese Originale de 5-Aryl (ou 5-benzyl)-2[(1-Diethoxyphosphonyl)methyl]-1,3,4-oxadiazoles par Action du Phosphonomethylhydrazide sur les Imidates <i>N</i>-Acyles
  作者：Abdallah Harizi

  DOI：10.1080/10426500600695047

  日期：2006.10.1

  The phosphonomethylhydrazide 2a reacts with N-acylated imidates 3a-d to give the corresponding 5-aryl (or 5-benzyl)-2-[(1-diethoxyphosphonyl)methyl]-1,3,4-oxadiazoles 4a-d after the elimination of ethanamide 5. Compounds 2a-e are prepared by the action of triethyl phosphonoacetate 1 with hydrazine and its derivatives. The structures of 1,3,4-oxadiazoles 4a-d and hydrazides 2a-e have been unequivocally confirmed by means of IR, H-1, C-13, P-31 NMR and mass spectrometry.