Dimethyl(3,3,3-trifluoro-2-oxopropyl)phosphonate | 85234-34-0

• 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: Dimethyl(3,3,3-trifluoro-2-oxopropyl)phosphonate
• 英文别名: 3-dimethoxyphosphoryl-1,1,1-trifluoropropan-2-one
• CAS: 85234-34-0
• 化学式: C₅H₈F₃O₄P
• 分子量: 220.085
• InChiKey: CIYLYRKRFOLKCO-UHFFFAOYSA-N

物化性质

• 沸点：
  209.5±40.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Dimethyl(3,3,3-trifluoro-2-oxopropyl)phosphonate 在 4-二甲氨基吡啶 、 Candida antarctica lipase B 、 N,N'-二环己基碳二亚胺 作用下， 以 正丁醇 、 苯 为溶剂， 反应 28.0h， 生成 (R)-dimethyl 3,3,3-trifluoro-2-hydroxypropanephosphonate
  参考文献：
  名称：

  Enzymatic synthesis of optically active trifluoromethylated 1- and 2-hydroxyalkanephosphonates

  摘要：

  Convenient enzymatic methods have been developed for the preparation of chiral 1- and 2-hydroxyalkanephosphonates bearing a trifluoromethyl moiety with high enantiomeric excess via Candida antarctica lipase B-, Mucor miehei lipase-catalyzed alcoholysis and C. rugosa lipase-catalyzed hydrolysis in organic media. The enantiomeric excess of such trifluoromethylated carbinols was determined using quinine as a chiral solvating agent. The catalytic preference was assigned according to the Kusumi-Ohtani method. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01559-4
• 作为产物：
  描述：

  三氟乙酰氯 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 2.75h， 生成 Dimethyl(3,3,3-trifluoro-2-oxopropyl)phosphonate
  参考文献：
  名称：

  LOW-CALCEMIC 16,23-DIENE 25-OXIME ANALOGS OF 1ALPHA,25-DIHYDROXY VITAMIN D3

  摘要：

  本发明提供了一种新颖的1,25-二羟基维生素D3的16,23-二烯-25-氧基醚类似物，包括含有这些化合物的组合物以及将这些化合物用作CYP24抑制剂的方法。特别是，本发明的这种新颖化合物对于治疗受益于调节1,25-二羟基维生素D3水平的疾病是有用的，例如，细胞增殖紊乱。

  公开号：

  US20090082317A1

文献信息

• Preparation of pyrimidine derivatives through three-component reactions of dialkyl (2-oxo-3,3,3-trifluoropropyl)phosphonates
  作者：V. M. Timoshenko、Yu. N. Markitanov、Yu. G. Shermolovich

  DOI：10.1007/s10593-011-0863-4

  日期：2011.11

  are proposed for the preparation of fluorophosphorus-containing pyrimidines through three- component reactions of dialkyl (3,3,3-trifluoro-2-oxopropyl)phosphonates. Cyclocondensation of these phosphonates with urea and aryl aldehydes gave 6-aryl-4-hydroxy-2-oxo-4-trifluoromethylhexa-hydropyrimidin-5-ylphosphonates and reaction with urea and trialkyl orthoformates led to 4-alkoxy-2-oxo-4-trifluoromethyl-1

  提出了通过（3,3,3-三氟-2-氧代丙基）膦酸二烷基酯的三组分反应制备含氟磷的嘧啶的方法。这些膦酸酯与脲和芳基醛的环缩合反应得到6-芳基-4-羟基-2-氧代-4-三氟甲基六氢嘧啶-5-基的膦酸酯，与脲和三烷基正甲酸酯反应生成4-烷氧基-2-氧代-4-三氟甲基1,2,3,4-四氢嘧啶-5-基膦酸酯。
• A convenient synthesis of perfluoroalkylated hydroxy- and dihydroxy-phosphonates
  作者：Wenbiao Cen、Xuezhen Dai、Yanchang Shen

  DOI：10.1016/s0022-1139(00)80472-8

  日期：1993.11

  Perfluoroalkylated 1-hydroxyphosphonates may be easily synthesized in good yield by the reaction of the corresponding perfluoroalkyl aldehydes with dimethyl phosphite. Perfluoroalkylcarboxylic esters react with the phosphonate anion to give (perfluoroacyl)methylphosphonates, their tautomeric isomers (2-perfluoroalkyl-2-hydroxy)vinylphosphonates and their hydrates (2-perfluoroalkyl-2,2-dihydroxy)ethylphosphonates, which are reduced with sodium borohydride affording perfluoroalkylated 2-hydroxyphosphonates in 61-68% yield. Perfluoroalkylated dihydroxyphosphonates may be obtained by the reaction of the bisphosphonate anion with perfluoroalkyl aldehydes followed by oxidation with osmium tetraoxide in 54-68% yield.
• LOW-CALCEMIC 16,23-DIENE 25-OXIME ANALOGS OF 1ALPHA,25-DIHYDROXY VITAMIN D3
  申请人：Saha Uttam

  公开号：US20090082317A1

  公开（公告）日：2009-03-26

  The present invention provides novel 16,23-diene 25-oxime ether analogs of 1,25-dihydroxy vitamin D3, compositions comprising these compounds and methods of using these compounds as inhibitors of CYP24. In particular, the novel compound of the invention are useful for treating diseases which benefit from a modulation of the levels of 1,25-dihydroxy vitamin D3, for example, cell-proliferative disorders.

  本发明提供了一种新颖的1,25-二羟基维生素D3的16,23-二烯-25-氧基醚类似物，包括含有这些化合物的组合物以及将这些化合物用作CYP24抑制剂的方法。特别是，本发明的这种新颖化合物对于治疗受益于调节1,25-二羟基维生素D3水平的疾病是有用的，例如，细胞增殖紊乱。
• Enzymatic synthesis of optically active trifluoromethylated 1- and 2-hydroxyalkanephosphonates
  作者：Yonghui Zhang、Jin-feng Li、Cheng-ye Yuan

  DOI：10.1016/s0040-4020(02)01559-4

  日期：2003.1

  Convenient enzymatic methods have been developed for the preparation of chiral 1- and 2-hydroxyalkanephosphonates bearing a trifluoromethyl moiety with high enantiomeric excess via Candida antarctica lipase B-, Mucor miehei lipase-catalyzed alcoholysis and C. rugosa lipase-catalyzed hydrolysis in organic media. The enantiomeric excess of such trifluoromethylated carbinols was determined using quinine as a chiral solvating agent. The catalytic preference was assigned according to the Kusumi-Ohtani method. (C) 2003 Elsevier Science Ltd. All rights reserved.