2-[(2-anilino-2-oxoacetyl)sulfanyl]ethyl acetate | 444346-72-9

• 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-[(2-anilino-2-oxoacetyl)sulfanyl]ethyl acetate
• 英文别名: Carboxin M6；2-(2-anilino-2-oxoacetyl)sulfanylethyl acetate
• CAS: 444346-72-9
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: OPSSOPWSPWUZME-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-anilino-2-oxoacetyl)sulfanyl]ethyl acetate 在 水 、 氧气 作用下， 反应 96.0h， 生成 2-羟乙基二硫化物 、 2-mercaptoethyl acetate 、 草酸一醯胺苯
  参考文献：
  名称：

  Phototransformation of Carboxin in Water. Toxicity of the Pesticide and Its Sulfoxide to Aquatic Organisms

  摘要：

  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.

  DOI：

  10.1021/jf049737o
• 作为产物：
  描述：

  萎锈灵 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以29%的产率得到2-[(2-anilino-2-oxoacetyl)sulfanyl]ethyl acetate
  参考文献：
  名称：

  取代基和溶剂对5，6-二氢-1,4-氧杂i子素的光敏氧化作用的影响。分子内氧转移与二氧环乙烷中间体的正常裂解。

  摘要：

  单线态氧与各种取代的氧杂环丁烷1的反应产生二羰基化合物4和/或酮亚砜7和8，这取决于C 3上取代基的性质和反应条件。二氧环乙烷2到4的正常断裂与分子内的氧转移竞争成环硫，这大概是通过不稳定的环氧化物5导致的7和8。这种新的途径是由C3上的吸电子基团促进的，对于未取代的和单取代的酰胺衍生物1h和1i分别通过溶剂呈碱性。化学实验支持7为环氧化物5的中间体，而对于8为环氧化物的结论并不明确。但是，后者的形成似乎受到极性溶剂和C2上的阳离子稳定基团（如苯基或甲基）的帮助。

  DOI：

  10.1021/jo020008m

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.
• Substituent and Solvent Effects on the Photosensitized Oxygenation of 5,6-Dihydro-1,4-oxathiins. Intramolecular Oxygen Transfer vs Normal Cleavage of the Dioxetane Intermediates
  作者：F. Cermola、M. R. Iesce

  DOI：10.1021/jo020008m

  日期：2002.7.1

  ketosulfoxides 7 and 8 depending on the nature of the substituent at C3 and on the reaction conditions. The normal fragmentation of dioxetanes 2 to 4 competes with an intramolecular oxygen transfer to ring sulfur, which leads to 7 and 8, presumably via the labile epoxides 5. This new pathway is promoted by electron-withdrawing groups at C3 and, for unsubstituted and monosubstituted amide derivatives 1h and 1i

  单线态氧与各种取代的氧杂环丁烷1的反应产生二羰基化合物4和/或酮亚砜7和8，这取决于C 3上取代基的性质和反应条件。二氧环乙烷2到4的正常断裂与分子内的氧转移竞争成环硫，这大概是通过不稳定的环氧化物5导致的7和8。这种新的途径是由C3上的吸电子基团促进的，对于未取代的和单取代的酰胺衍生物1h和1i分别通过溶剂呈碱性。化学实验支持7为环氧化物5的中间体，而对于8为环氧化物的结论并不明确。但是，后者的形成似乎受到极性溶剂和C2上的阳离子稳定基团（如苯基或甲基）的帮助。