nitrosoparathion | 55290-76-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: nitrosoparathion
• 英文别名: Diethoxy-(4-nitrosophenoxy)-sulfanylidene-lambda5-phosphane；diethoxy-(4-nitrosophenoxy)-sulfanylidene-λ5-phosphane
• CAS: 55290-76-1
• 化学式: C₁₀H₁₄NO₄PS
• 分子量: 275.265
• InChiKey: DIKOHIKCUWASMX-UHFFFAOYSA-N

物化性质

• 沸点：
  341.1±44.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  nitrosoparathion 在 维生素 C 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以30.9%的产率得到O,O-diethyl O-(4-hydroxyaminophenyl) thiophosphate
  参考文献：
  名称：

  Aminoparathion: A Highly Reactive Metabolite of Parathion. 1. Reactions with Polyphenols and Polyphenol Oxidase

  摘要：

  Spiking of tomato and apple fruits with parathion at different levels of about 1-4 mg/kg irradiation and under simulated sunlight conditions resulted in nearly complete photodegradation within 13 h, but extractable parathion degradation products could not be found in any case. However, after irradiation of an unrealistically spiked apple (134 mg/kg) different photoproducts including aminoparathion (AP) were detectable by HPLC, proving that the hitherto postulated photochemistry of parathion indeed takes place in the fruit cuticle environment. Besides the photoreduction pathway it was shown for the first time that AP is also easily formed by reduction of the primary photoproduct nitrosoparathion with thiols (cysteine, glutathione), while ascorbic acid only leaves hydroxylaminoparathion. In the presence of polyphenols, AP was effectively bound to quinone intermediates formed by both silver oxide and polyphenol oxidases. For pyrocatechol, a disubstituted o-quinone derivative could be isolated as a dark red addition product and structurally be elucidated. However, in the presence of caffeic acid, catechol, naringin, and quercetin, respectively, insoluble dark colored polymers precipitated within 48 h, while in the supernatants AP was not detectable any more. Polymer-bound and nonextractable AP was proven by transesterification with sodium ethoxide releasing O,O,O-triethyl thiophosphate which was determined by GC. Additionally, AP itself was a substrate for polyphenol oxidases, resulting in a quinone imine intermediate which in turn reacted with excessive AP yielding deep red colored di- and trimerization products.

  DOI：

  10.1021/jf051520m
• 作为产物：
  描述：

  巴拉松 在 铁粉 作用下， 以 甲醇 为溶剂， 生成 nitrosoparathion
  参考文献：
  名称：

  Reduction of Nitro Aromatic Compounds by Zero-Valent Iron Metal

  摘要：

  The properties of iron metal that make it useful in remediation of chlorinated solvents may also lead to reduction of other groundwater contaminants such as nitro aromatic compounds (NACs). Nitrobenzene is reduced by iron under anaerobic conditions to aniline with nitrosobenzene as an intermediate product. Coupling products such as azobenzene and azoxybenzene were not detected. First-order reduction rates are similar for nitrobenzene and nitrosobenzene, but aniline appearance occurs more slowly (typical pseudo-first-order rate constants 3.5 x 10(-2), 3.4 x 10(-2), and 8.8 x 10(-3) min(-1), respectively, in the presence of 33 g/L acid-washed, 18-20 mesh Fluka iron turnings). The nitro reduction rate increased linearly with concentration of iron surface area, giving a specific reaction rate constant (3.9 +/- 0.2 x 10(-2) min(-1) m(-2) L). The minimal effects of solution pH or ring substitution on nitro reduction rates, and the linear correlation between nitrobenzene reduction rare constants and the square-root of mixing rate (rpm), suggest that the observed reaction rates were controlled by mass transfer of the NAC to the metal surf:ace. The decrease in reduction rate for nitrobenzene with increased concentration of dissolved carbonate and with extended exposure of the metal to a particular carbonate buffer indicate that the precipitation of side rite on the metal inhibits nitro reduction.

  DOI：

  10.1021/es950211h

文献信息

• RECOMBINANT ORGANOPHOSPHOROUS ACID ANHYDRASE AND METHODS OF USE
  申请人：MCDANIEL C. STEVEN

  公开号：US20080206834A1

  公开（公告）日：2008-08-28

  The bacterial gene (opd) encodes an organophosphorus anhydrase which is capable of hydrolyzing a wide spectrum of neurotoxins ranging from insecticides to mammalian neurotoxins. The cloned gene has been expressed in a number of hosts and the purified enzyme has been characterized. These advances have led to a number of interrelated uses for the cloned gene and the recombinant enzyme including: detoxification of organophosphorus compounds; detection of organophosphorus compounds; protection of susceptible organisms from organophosphorus poisoning; and, detection of organophosphorus-detoxifying microorganisms.
• Reduction of Nitro Aromatic Compounds by Zero-Valent Iron Metal
  作者：Abinash Agrawal、Paul G. Tratnyek

  DOI：10.1021/es950211h

  日期：1996.12.1

  The properties of iron metal that make it useful in remediation of chlorinated solvents may also lead to reduction of other groundwater contaminants such as nitro aromatic compounds (NACs). Nitrobenzene is reduced by iron under anaerobic conditions to aniline with nitrosobenzene as an intermediate product. Coupling products such as azobenzene and azoxybenzene were not detected. First-order reduction rates are similar for nitrobenzene and nitrosobenzene, but aniline appearance occurs more slowly (typical pseudo-first-order rate constants 3.5 x 10(-2), 3.4 x 10(-2), and 8.8 x 10(-3) min(-1), respectively, in the presence of 33 g/L acid-washed, 18-20 mesh Fluka iron turnings). The nitro reduction rate increased linearly with concentration of iron surface area, giving a specific reaction rate constant (3.9 +/- 0.2 x 10(-2) min(-1) m(-2) L). The minimal effects of solution pH or ring substitution on nitro reduction rates, and the linear correlation between nitrobenzene reduction rare constants and the square-root of mixing rate (rpm), suggest that the observed reaction rates were controlled by mass transfer of the NAC to the metal surf:ace. The decrease in reduction rate for nitrobenzene with increased concentration of dissolved carbonate and with extended exposure of the metal to a particular carbonate buffer indicate that the precipitation of side rite on the metal inhibits nitro reduction.
• Aminoparathion: A Highly Reactive Metabolite of Parathion. 1. Reactions with Polyphenols and Polyphenol Oxidase
  作者：Bruno Rung、Wolfgang Schwack

  DOI：10.1021/jf051520m

  日期：2005.11.1

  Spiking of tomato and apple fruits with parathion at different levels of about 1-4 mg/kg irradiation and under simulated sunlight conditions resulted in nearly complete photodegradation within 13 h, but extractable parathion degradation products could not be found in any case. However, after irradiation of an unrealistically spiked apple (134 mg/kg) different photoproducts including aminoparathion (AP) were detectable by HPLC, proving that the hitherto postulated photochemistry of parathion indeed takes place in the fruit cuticle environment. Besides the photoreduction pathway it was shown for the first time that AP is also easily formed by reduction of the primary photoproduct nitrosoparathion with thiols (cysteine, glutathione), while ascorbic acid only leaves hydroxylaminoparathion. In the presence of polyphenols, AP was effectively bound to quinone intermediates formed by both silver oxide and polyphenol oxidases. For pyrocatechol, a disubstituted o-quinone derivative could be isolated as a dark red addition product and structurally be elucidated. However, in the presence of caffeic acid, catechol, naringin, and quercetin, respectively, insoluble dark colored polymers precipitated within 48 h, while in the supernatants AP was not detectable any more. Polymer-bound and nonextractable AP was proven by transesterification with sodium ethoxide releasing O,O,O-triethyl thiophosphate which was determined by GC. Additionally, AP itself was a substrate for polyphenol oxidases, resulting in a quinone imine intermediate which in turn reacted with excessive AP yielding deep red colored di- and trimerization products.