5-ethyl-2-phenyl-6-trifluoromethanesulfonyloxy-3-(3-trimethylsilyl)propargyl-4(3H)-pyrimidinone | 192802-92-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 5-ethyl-2-phenyl-6-trifluoromethanesulfonyloxy-3-(3-trimethylsilyl)propargyl-4(3H)-pyrimidinone
• 英文别名: [5-Ethyl-6-oxo-2-phenyl-1-(3-trimethylsilylprop-2-ynyl)pyrimidin-4-yl] trifluoromethanesulfonate
• CAS: 192802-92-9
• 化学式: C₁₉H₂₁F₃N₂O₄SSi
• 分子量: 458.533
• InChiKey: CGECGYIURIUGBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-ethyl-2-phenyl-6-trifluoromethanesulfonyloxy-3-(3-trimethylsilyl)propargyl-4(3H)-pyrimidinone 在 四(三苯基膦)钯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-Ethyl-6-oxo-2-phenyl-1-prop-2-ynyl-1,6-dihydro-pyrimidine-4-carbonitrile
  参考文献：
  名称：

  6-Trifluoromethanesulfonyloxy-4(3H)-pyrimidinones as versatile intermediates for the synthesis of 6-functionalized 4(3H)-pyrimidinones

  摘要：

  The reaction of 6-trifluoromethanesulfonyloxy-4(3H)-pyrimidinones with Me2Cu(CN)Li-2, and with vinyl tributyltin, trimethylsilylacetylene, and zinc cyanide with palladium catalysis, are described for the synthesis of a variety of fully functionalized 6-substituted-4(3H)-pyrimidinones of interest as herbicides.

  DOI：

  10.1016/s0040-4039(97)00947-7
• 作为产物：
  描述：

  5-ethyl-6-hydroxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone 在 2,3,5-三甲基吡啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 生成 5-ethyl-2-phenyl-6-trifluoromethanesulfonyloxy-3-(3-trimethylsilyl)propargyl-4(3H)-pyrimidinone
  参考文献：
  名称：

  6-Trifluoromethanesulfonyloxy-4(3H)-pyrimidinones as versatile intermediates for the synthesis of 6-functionalized 4(3H)-pyrimidinones

  摘要：

  The reaction of 6-trifluoromethanesulfonyloxy-4(3H)-pyrimidinones with Me2Cu(CN)Li-2, and with vinyl tributyltin, trimethylsilylacetylene, and zinc cyanide with palladium catalysis, are described for the synthesis of a variety of fully functionalized 6-substituted-4(3H)-pyrimidinones of interest as herbicides.

  DOI：

  10.1016/s0040-4039(97)00947-7

文献信息

• Process for pyrimidinone compounds
  申请人：Princeton University

  公开号：US05889184A1

  公开（公告）日：1999-03-30

  This invention relates to a process for the preparation of pyrimidinone compounds of the formula ##STR1## wherein Ar is an optionally substituted aryl or heteroaromatic moiety, R.sup.3 is an optionally substituted alkyl, alkenyl or alkynyl, R.sup.5 is a hydrogen atom, halo, cyano or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthio, and R.sup.6 is a hydrogen atom, cyano, or an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl. The process comprises reaction of an amidine and a malonic acid derivative to give a hydroxypyrimidinone followed by conversion of the resulting hydroxypyrimidinone to a sulfonyloxypyrimidinone followed by reaction of the resulting sulfonyloxypyrimidinone with an organometallic reagent to give the desired pyrimidinone. The hydroxypyrimidinones, wherein R.sup.6 is hydroxy and sulfonyloxypyrimidinones wherein R.sup.6 is a substituted sulfonyloxy moiety, are themselves new and useful intermediates in the preparation of the desired pyrimidinones.

  这项发明涉及一种制备嘧啶酮化合物的过程，其化学式为##STR1##其中Ar是一个可选择取代的芳基或杂环芳基，R.sup.3是一个可选择取代的烷基、烯基或炔基，R.sup.5是一个氢原子、卤素、氰基或一个可选择取代的烷基、烯基、炔基、烷氧基或硫代烷基，R.sup.6是一个氢原子、氰基，或一个可选择取代的烷基、环烷基、烯基、炔基、芳基、芳基烷基或杂环芳基。该过程包括使脲酰胺和丙二酸衍生物反应，得到羟基嘧啶酮，然后将所得的羟基嘧啶酮转化为磺酰氧基嘧啶酮，随后将所得的磺酰氧基嘧啶酮与有机金属试剂反应，得到所需的嘧啶酮。其中R.sup.6为羟基的羟基嘧啶酮和R.sup.6为取代磺酰氧基的磺酰氧基嘧啶酮本身是制备所需嘧啶酮的新颖有用的中间体。
• Improved process for pyrimidinone compounds
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0812832A1

  公开（公告）日：1997-12-17

  This invention relates to a process for the preparation of pyrimidinone compounds of the formula wherein Ar is an optionally substituted aryl or heteroaromatic moiety, R3 is an optionally substituted alkyl, alkenyl, alkynyl, (C1-C6)alkoxy (C2-C6)alkyl or silyl (C3-C6)alkynyl, R5 is a hydrogen atom, halo, cyano or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthio, and R6 is a hydrogen atom, cyano, or an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl. The process comprises reaction of an amidine and a malonic acid derivative to give a hydroxypyrimidinone followed by conversion of the resulting hydroxypyrimidinone to a sulfonyloxypyrimidinone followed by reaction of the resulting sulfonyloxypyrimidinone with an organometallic reagent to give the desired pyrimidinone. The hydroxypyrimidinones, wherein R6 is hydroxy and sulfonyloxypyrimidinones wherein R6 is a substituted sulfonyloxy moiety, are themselves new and useful intermediates in the preparation of the desired pyrimidinones.

  这项发明涉及一种用于制备公式为的吡啶酮化合物的工艺 其中 Ar是可选地取代的芳香族或杂芳基部分， R3是可选地取代的烷基、烯基、炔基、(C1-C6)alkoxy (C2-C6)alkyl或硅基(C3-C6)炔基， R5是氢原子、卤素、氰基或可选地取代的烷基、烯基、炔基、烷氧基或烷硫基，和 R6是氢原子、氰基，或可选地取代的烷基、环烷基、烯基、炔基、芳香族、芳烷基或杂芳基。 该工艺包括将酰胺与马来酸衍生物反应以给出羟基吡啶酮，然后将所得羟基吡啶酮转化为磺酰氧基吡啶酮，然后将所得磺酰氧基吡啶酮与有机金属试剂反应以得到所需的吡啶酮。 其中R6是羟基的羟基吡啶酮和其中R6是取代磺酰氧基基团的磺酰氧基吡啶酮本身就是用于制备所需吡啶酮的新颖有用的中间体。