2-methyl-1,3-oxathiolane-N-phenyl-2-ketocarboxamide | 64754-74-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methyl-1,3-oxathiolane-N-phenyl-2-ketocarboxamide
• 英文别名: 2-Methyl-1,3-oxathiolane-2-carbonylcarboxanilide；2-(2-methyl-[1,3]oxathiolan-2-yl)-2-oxo-N-phenyl-acetamide；2-Methyl-1,3-oxathiolan-2-ketocarboxanilid；2-(2-methyl-1,3-oxathiolan-2-yl)-2-oxo-N-phenylacetamide
• CAS: 64754-74-1
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: NNTMFUVUOMQASS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-1,3-oxathiolane-N-phenyl-2-ketocarboxamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以64%的产率得到α-hydroxy-2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide
  参考文献：
  名称：

  Conversion of Dihydro-1,4-oxathiin-3-carboxamide to the Isomeric Dihydro-1,4-oxathiin-2-carboxamide

  摘要：

  The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathiin (1) via dichloro-1,4-oxathiane (4) is described. Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5). The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8). Dehydration of 5 followed by reduction afforded alpha-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3). The reason for more facile displacement of chlorine at C-2 in comparison with that at C-3 in 4 was also discussed.

  DOI：

  10.3987/com-94-6944
• 作为产物：
  描述：

  2,3-dihydroxy-2-methyl-N-phenyl-1,4-oxathiane-3-carboxyamide 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 以77%的产率得到2-methyl-1,3-oxathiolane-N-phenyl-2-ketocarboxamide
  参考文献：
  名称：

  Conversion of Dihydro-1,4-oxathiin-3-carboxamide to the Isomeric Dihydro-1,4-oxathiin-2-carboxamide

  摘要：

  The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathiin (1) via dichloro-1,4-oxathiane (4) is described. Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5). The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8). Dehydration of 5 followed by reduction afforded alpha-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3). The reason for more facile displacement of chlorine at C-2 in comparison with that at C-3 in 4 was also discussed.

  DOI：

  10.3987/com-94-6944

文献信息

• Phototransformation of Carboxin in Water. Toxicity of the Pesticide and Its Sulfoxide to Aquatic Organisms
  作者：Marina DellaGreca、Maria Rosaria Iesce、Flavio Cermola、Maria Rubino、Marina Isidori

  DOI：10.1021/jf049737o

  日期：2004.10.1

  Sunlight exposure of aqueous suspensions of carboxin (1) causes its phototransformation to sulfoxide 2 and minor components. Similar effects are observed in the presence of humic acid or nitrate or at different pH values. Photoproducts 2-9 were isolated by chromatographic techniques and/or identified by spectroscopic means. Carboxin 1 and its main photoproduct sulfoxide 2 were tested to evaluate acute toxicity to primary consumers typical of the aquatic environment: the rotifer Brachionus calyciflorus and two crustaceans, Daphnia magna and Thamnocephalus platyurus. Chronic tests comprised a producer, the alga Pseudokirchneriella subcapitata, and a consumer, the crustacean Ceriodaphnia dubia.
• Additive Pummerer-initiated functionalization of allylic methyl groups in acrylic acid derived systems
  作者：Russell R. King

  DOI：10.1021/jo01314a028

  日期：1980.12
• KING R. R., J. ORG. CHEM., 1980, 45, NO 26, 5347-5349
  作者：KING R. R.

  DOI：——

  日期：——
• KING R. R.; GREENHALGH R.; MARSHALL D. W., J. ORG. CHEM., 1978, 43, NO 6, 1262-1263
  作者：KING R. R.、 GREENHALGH R.、 MARSHALL D. W.

  DOI：——

  日期：——