ethyl 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin-3-carboxylate | 304677-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环己烯
• 英文名称: ethyl 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin-3-carboxylate
• 英文别名: 6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylic acid ethylester；ethyl 6-(trifluoromethyl)-2,3-dihydro-1,4-oxathiine-5-carboxylate
• CAS: 304677-92-7
• 化学式: C₈H₉F₃O₃S
• 分子量: 242.219
• InChiKey: YWIMWQSOMMWRMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin-3-carboxylate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylic acid chloride
  参考文献：
  名称：

  Synthesis of Trifluoromethylated Dihydro-1,4-oxathiin-3-carboxanilides through Polymer-bound Activated Ester

  摘要：

  A synthesis of new trifluoromethylated dihydro-1,4-oxathiin-3-carboxanilids (2) through polymer-bound activated ester is described. Chlorination of ethyl gamma,gamma,gamma-trifluoroacetoacetate (3) followed by treatment of 2-mercaptoethanol gave hydroxyoxathianes isomers (cis-10 and trans-11). Replacement of hydroxy to chlorine and then dehydrochlorination afforded trifluoromethyl dihydro-1,4-oxathiin ester (7). The polymer-bound trifluoromethylated dihydro-1,4-oxathiin-3-carboxylic acid, 4-hydroxy-3-nitrobenzophenone ester (16) was prepared through the reaction of polystyrene-bound 4-hydroxy-3-nitrobenzophenone (14) with the trifluoromethylated dihydro-1,4-oxathiin-3-carbonyl chloride (15). Refluxing of 16 with anilines in acetonitrile gave the corresponding carboxanilide (2). The reaction rate depended on the nucelophilicity of nitrogen in aniline.

  DOI：

  10.3987/com-98-8290
• 作为产物：
  描述：

  ethyl α-(2-hydroxyethylthio)-γ,γ,γ-trifluoroacetoacetate 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 22.5h， 以59.4%的产率得到ethyl 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin-3-carboxylate
  参考文献：
  名称：

  [DE] OXATHIINCARBOXAMIDE
  [EN] OXATHIIN CARBOXAMIDE
  [FR] OXATHIINE-CARBOXAMIDES

  摘要：

  公开号：

  WO2004072023A3

文献信息

• Oxathiin carboxamide
  申请人：Dunkel Ralf

  公开号：US20070004793A1

  公开（公告）日：2007-01-04

  This invention relates to novel oxathiincarboxamides of the formula (I) in which G 1 , G 2 , G 3 , n, R 1 , R 2 , R 3 , R 4 , R 5 and Z are as defined in the disclosure, to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.

  本发明涉及公式（I）的新颖的噁嗪羧酰胺化合物，其中G1、G2、G3、n、R1、R2、R3、R4、R5和Z如披露中所定义，以及制备这些化合物的多种方法和它们用于控制不良微生物的用途，还涉及新的中间体及其制备。
• US7847108B2
  申请人：——

  公开号：US7847108B2

  公开（公告）日：2010-12-07
• [DE] OXATHIINCARBOXAMIDE<br/>[EN] OXATHIIN CARBOXAMIDE<br/>[FR] OXATHIINE-CARBOXAMIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2004072023A3

  公开（公告）日：2005-04-07
• Synthesis of Trifluoromethylated Dihydro-1,4-oxathiin-3-carboxanilides through Polymer-bound Activated Ester
  作者：Hoh-Gyu Hahn、Kee Hyuk Chang、Kee Dal Nam、Su Yeoul Bae、Heduck Mah

  DOI：10.3987/com-98-8290

  日期：——

  A synthesis of new trifluoromethylated dihydro-1,4-oxathiin-3-carboxanilids (2) through polymer-bound activated ester is described. Chlorination of ethyl gamma,gamma,gamma-trifluoroacetoacetate (3) followed by treatment of 2-mercaptoethanol gave hydroxyoxathianes isomers (cis-10 and trans-11). Replacement of hydroxy to chlorine and then dehydrochlorination afforded trifluoromethyl dihydro-1,4-oxathiin ester (7). The polymer-bound trifluoromethylated dihydro-1,4-oxathiin-3-carboxylic acid, 4-hydroxy-3-nitrobenzophenone ester (16) was prepared through the reaction of polystyrene-bound 4-hydroxy-3-nitrobenzophenone (14) with the trifluoromethylated dihydro-1,4-oxathiin-3-carbonyl chloride (15). Refluxing of 16 with anilines in acetonitrile gave the corresponding carboxanilide (2). The reaction rate depended on the nucelophilicity of nitrogen in aniline.