Methoxy-methylsulfanyl-(4-nitrophenoxy)-sulfanylidene-lambda5-phosphane | 1195996-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methoxy-methylsulfanyl-(4-nitrophenoxy)-sulfanylidene-lambda5-phosphane
• 英文别名: methoxy-methylsulfanyl-(4-nitrophenoxy)-sulfanylidene-λ5-phosphane
• CAS: 1195996-17-8
• 化学式: C₈H₁₀NO₄PS₂
• 分子量: 279.277
• InChiKey: FGGSMYOVAOWNCB-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methoxy-methylsulfanyl-(4-nitrophenoxy)-sulfanylidene-lambda5-phosphane 在 K-10 montmorillonite 、 碘酰苯 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以43%的产率得到(R)-isoparathion methyl
  参考文献：
  名称：

  Biocatalytic oxidation of thiophosphoryl compounds: a new chemo-enzymatic approach to enantiomeric insecticidal thionophosphates and their oxons

  摘要：

  The biocatalytic oxidation of racemic O-S-dimethyl O-p-nitrophenyl phosphorodithioate 5 catalyzed by chloroperoxidase from Caldariomyces fumago resulted in the formation of the (-)-(S)-enantiomer of the corresponding oxon 4 and unoxidized substrate 5 with a (+)-(R)-configuration. Both compounds were obtained with very high enantiomeric excesses, 99.6% and 97%, respectively. The thionation reaction of the resulting (-)-(S)-oxon 4 with Lawesson's reagent gave (-)-(S)-phosphorodithioate 5 with full stereoselectivity, while the oxidation of unreacted substrate (+)-(R)-5 with iodoxybenzene afforded oxon (+)-(R)-4 with 94.9% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.031
• 作为产物：
  描述：

  (R)-isoparathion methyl 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以74.5%的产率得到Methoxy-methylsulfanyl-(4-nitrophenoxy)-sulfanylidene-lambda5-phosphane
  参考文献：
  名称：

  Biocatalytic oxidation of thiophosphoryl compounds: a new chemo-enzymatic approach to enantiomeric insecticidal thionophosphates and their oxons

  摘要：

  The biocatalytic oxidation of racemic O-S-dimethyl O-p-nitrophenyl phosphorodithioate 5 catalyzed by chloroperoxidase from Caldariomyces fumago resulted in the formation of the (-)-(S)-enantiomer of the corresponding oxon 4 and unoxidized substrate 5 with a (+)-(R)-configuration. Both compounds were obtained with very high enantiomeric excesses, 99.6% and 97%, respectively. The thionation reaction of the resulting (-)-(S)-oxon 4 with Lawesson's reagent gave (-)-(S)-phosphorodithioate 5 with full stereoselectivity, while the oxidation of unreacted substrate (+)-(R)-5 with iodoxybenzene afforded oxon (+)-(R)-4 with 94.9% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.031

文献信息

• Biocatalytic oxidation of thiophosphoryl compounds: a new chemo-enzymatic approach to enantiomeric insecticidal thionophosphates and their oxons
  作者：Marian Mikołajczyk、Jerzy Łuczak、Piotr Kiełbasiński、Stefano Colonna

  DOI：10.1016/j.tetasy.2009.07.031

  日期：2009.8

  The biocatalytic oxidation of racemic O-S-dimethyl O-p-nitrophenyl phosphorodithioate 5 catalyzed by chloroperoxidase from Caldariomyces fumago resulted in the formation of the (-)-(S)-enantiomer of the corresponding oxon 4 and unoxidized substrate 5 with a (+)-(R)-configuration. Both compounds were obtained with very high enantiomeric excesses, 99.6% and 97%, respectively. The thionation reaction of the resulting (-)-(S)-oxon 4 with Lawesson's reagent gave (-)-(S)-phosphorodithioate 5 with full stereoselectivity, while the oxidation of unreacted substrate (+)-(R)-5 with iodoxybenzene afforded oxon (+)-(R)-4 with 94.9% ee. (C) 2009 Elsevier Ltd. All rights reserved.