diisopropyl ethyl phosphonothiolformate | 163678-86-2

• 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: diisopropyl ethyl phosphonothiolformate
• 英文别名: S-ethyl di(propan-2-yloxy)phosphorylmethanethioate
• CAS: 163678-86-2
• 化学式: C₉H₁₉O₄PS
• 分子量: 254.287
• InChiKey: AZKJBAUGYZCQSH-UHFFFAOYSA-N

物化性质

• 沸点：
  301.7±25.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diisopropyl ethyl phosphonothiolformate 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 72.0h， 以54%的产率得到二异丙基亚磷酰胺
  参考文献：
  名称：

  Spontaneous Lossen Rearrangement of (Phosphonoformyl)hydroxamates. The Migratory Aptitude of the Phosphonyl Group

  摘要：

  (i-PrO)(2)P(=O)COSEt (1) reacted with NH2OH in pyridine at room temperature to give mainly (i-PrO)(2)P(=O)NH2 (4). The formation of 4 was interpreted in terms of a spontaneous Lessen rearrangement of (i-PrO)(2)P(=O)CONHOH (2a) formed in the reaction. A transient (PNMR)-P-31 signal appearing in the reaction mixture at delta -1.8 was assigned to 2a. Trapping of (i-PrO)(2)P(=O)N=C=O (5), formed in the reaction of 1 and NH2OH, by cyclohexylamine gave (i-PrO)(2)P(=O)NHCONHC6H11 (6). Attempted isolation of 6 gave the hydrolyzed product N-cyclohexylurea (7). The reaction of 1 with NH2OMe proceeded slower than that with NH2OH and gave the expected (i-PrO)(2)P(=O)CONHOMe (2b), which was isolated and identified. 2b converts slowly to 4 in pyridine at room temperature. In contrast, MeNHOH reacted rapidly with 1 and gave the stable crystalline (i-PrO)(2)P(=O)CON(Me)OH (2c). The structure of hydroxamates 2 were assigned on the basis of H-1, C-13, and P-31 NMR spectral data. This facile Lossen rearrangement is discussed in terms of the unusually high migratory aptitude of the phosphonyl group.

  DOI：

  10.1021/jo962075k
• 作为产物：
  描述：

  三异丙基亚磷酸酯 、 硫代氯甲酸乙酯 以 甲苯 为溶剂， 反应 3.0h， 生成 diisopropyl ethyl phosphonothiolformate
  参考文献：
  名称：

  Salomon, Claudio J.; Breuer, Eli, Synlett, 2000, # 6, p. 815 - 816

  摘要：

  DOI：

文献信息

• Compositions comprising oxophosphonate-based metalloproteinase inhibitors
  申请人：Yissum Research Development Company of the Hebrew University of Jerusalem

  公开号：US07101864B1

  公开（公告）日：2006-09-05

  The present invention relates to compositions useful for treating or controlling disease states or conditions associated with zinc containing proteinases, especially metalloproteinases. The active ingredient in these compositions is an alpha-oxo- or alpha-thixophosphpnate of formula (I). Out of the phosphonates of formula (I), some are known and others are new. The novel compounds constitute another aspect of the invention.

  本发明涉及用于治疗或控制与含锌蛋白酶，特别是金属蛋白酶相关的疾病状态或病况的组合物。这些组合物中的活性成分是具有化学式(I)的α-氧代或α-硫代膦酸酯。在化学式(I)的膦酸酯中，有些是已知的，而另一些是新的。这些新化合物构成了本发明的另一个方面。
• [EN] CARJBAMOYLPHOSPHONATES AS INHIBITORS AND USES THEREOF<br/>[FR] CARBAMOYLPHOSPHONATES EN TANT QU'INHIBITEURS ET LEURS UTILISATIONS
  申请人：YISSUM RES DEV CO

  公开号：WO2010089752A1

  公开（公告）日：2010-08-12

  The present invention relates to novel metalloproteinase inhibitors having an aryloxybenzenesulfonamide moiety and a carbamoylphosphonic acid moiety, to pharmaceutical compositions comprising them, and to their uses in the prevention and/or treatment of disease or disorder associated with MMP.

  本发明涉及具有芳氧基苯磺酰胺基团和氨基甲酰磷酸基团的新型金属蛋白酶抑制剂，以及包含它们的药物组合物，以及它们在预防和/或治疗与MMP相关的疾病或紊乱中的用途。
• CARBAMOYLPHOSPHONATES AS INHIBITORS AND USES THEREOF
  申请人：Breuer Eli

  公开号：US20120035140A1

  公开（公告）日：2012-02-09

  The present invention relates to novel metalloproteinase inhibitors having an aryloxybenzenesulfonamide moiety and a carbamoylphosphonic acid moiety, to pharmaceutical compositions comprising them, and to their uses in the prevention and/or treatment of disease or disorder associated with MMP.

  本发明涉及具有芳氧基苯磺酰胺基团和氨基甲酰磷酸基团的新型金属蛋白酶抑制剂，涉及包含它们的制药组合物，以及它们在预防和/或治疗与MMP相关的疾病或疾病中的应用。
• Kovalenko, L. V.; Buvashkina, N. I.; Sosnov, A. V., Russian Journal of General Chemistry, 1994, vol. 64, # 10.1, p. 1456 - 1459
  作者：Kovalenko, L. V.、Buvashkina, N. I.、Sosnov, A. V.

  DOI：——

  日期：——
• US8993544B2
  申请人：——

  公开号：US8993544B2

  公开（公告）日：2015-03-31