(S)-malaoxon | 145307-19-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-malaoxon
• 英文别名: diethyl (2S)-2-dimethoxyphosphorylsulfanylbutanedioate
• CAS: 145307-19-3
• 化学式: C₁₀H₁₉O₇PS
• 分子量: 314.296
• InChiKey: WSORODGWGUUOBO-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (-)-S-malathion 在 单过氧邻苯二甲酸 、 magnesium salt 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以53%的产率得到(S)-malaoxon
  参考文献：
  名称：

  Stereoselective and chemoselective oxidation of phosphorothionates using MMPP

  摘要：

  MMPP (monoperoxyphthalic acid, magnesium salt) converts phosphorothionates to the corresponding oxons in good yield with excellent chemoselectivity and stereoselectivity.

  DOI：

  10.1016/s0040-4039(00)60006-0

文献信息

• Enantiomeric separation of malathion and malaoxon and the chiral residue analysis in food and environmental matrix
  作者：Yifan Hua、Qian Zhou、Peng Wang、Zhiqiang Zhou、Donghui Liu

  DOI：10.1002/chir.23229

  日期：2020.8

  used chiral phosphorus insecticide, which has a more toxic chiral metabolite malaoxon. In this work, the enantiomers of malathion and malaoxon were separated by high‐performance liquid chromatography‐mass/mass (HPLC‐MS/MS) with chiral columns using acetonitrile/water or methanol/water as mobile phase, and the chromatographic conditions were optimized. Based on the chiral separation, the chiral residue

  马拉硫磷是一种广泛使用的手性磷杀虫剂，它具有更强的手性代谢产物马拉oxon。在这项工作中，使用乙腈/水或甲醇/水作为流动相的高效液相色谱-质量/质量（HPLC-MS / MS）手性色谱柱分离了马拉硫磷和马拉松的对映体，并优化了色谱条件。基于手性分离，建立了土壤，水果和蔬菜中对映体的手性残留分析方法。在CHIRALPAK IC手性色谱柱上可以更好地分离两对对映异构体，并以乙腈/水（40/60，v / v）作为流动相，以0.5 mL / min的流速实现马拉硫磷和丙二酮对映体的基线同时分离。通过旋光检测器测得的马拉硫磷和马拉松的洗脱顺序为-/ +。通过线性，回收率，精密度，检测限（LOD）和定量限（LOQ）验证了土壤，水果和蔬菜中的手性残留物分析。马拉硫磷对映体的LOD和LOQ为1μg/ kg，3-5μg/ kg，0.08μg/ kg和0.20–0.25μg/ kg。在0.02-12 mg /
• Enantioselective Interaction of Acid α-Naphthyl Acetate Esterase with Chiral Organophosphorus Insecticides
  作者：Anping Zhang、Jianqiang Sun、Chunmian Lin、Xiaoyan Hu、Weiping Liu

  DOI：10.1021/jf404959v

  日期：2014.2.19

  Many previous works have demonstrated that acetylcholinesterase (AChE) was enantioselectively inhibited by chiral organophosphorus insecticides (OPs) and that a significant difference in reactivation existed for AChE inactivated by (1R)-versus (1S,3S)-stereoisomers of isomalathion. It had been known that a-naphthyl acetate esterase (ANAE), an enzyme which might play an essential role in the growth of plants and the defense of plants against environmental stress by regulating the concentration of hormones in plants, can be inhibited by OPs. However, it was unknown whether interaction of ANAE with chiral OPs was enantioselective. The present work investigated the inhibition kinetics and spontaneous reactivation of ANAE inactivated by enantiomers of malaoxon, isomalathion, and methamidophos. The order of inhibition potency is (R) > (S) for malaoxon, (1R,3R) > (1R,3S) > (1S,3R) > (1S,3S) for isomalathion, and (S) > (R) for methamidophos according to bimolecular rate constants of inhibition (k(i)), which is consistent with the order observed in the enantioselective inhibition of AChE by malaoxon, isomalathion, and methamidophos. The difference in spontaneous reactivation of AChE inactivated between (1R)and (1S,3S)-isomers of isomalathion is conserved for ANAE. The observations indicated ANAE and AChE have similar selective inhibition kinetics and postinhibitory reactions in reaction with chiral OPs.
• Stereoselective and chemoselective oxidation of phosphorothionates using MMPP
  作者：John A. Jackson、Clifford E. Berkman、Charles M. Thompson

  DOI：10.1016/s0040-4039(00)60006-0

  日期：1992.10

  MMPP (monoperoxyphthalic acid, magnesium salt) converts phosphorothionates to the corresponding oxons in good yield with excellent chemoselectivity and stereoselectivity.