甲氧基-二(4-硝基苯氧基)-硫代膦烷 | 39004-94-9

• 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
• 中文名称: 甲氧基-二(4-硝基苯氧基)-硫代膦烷
• 英文名称: thiophosphoric acid O-methyl ester-O',O''-bis-(4-nitro-phenyl ester)
• 英文别名: Thiophosphorsaeure-O-methylester-O',O''-bis-(4-nitro-phenylester)；O-Methyl-O,O-bis-<4-nitro-phenyl>-thiophosphat；Phosphorothioic acid, O,O-bis(p-nitrophenyl) O-methyl ester；methoxy-bis(4-nitrophenoxy)-sulfanylidene-λ5-phosphane
• CAS: 39004-94-9
• 化学式: C₁₃H₁₁N₂O₇PS
• 分子量: 370.279
• InChiKey: AQAXQJMWHPFBPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2920190090

反应信息

• 作为反应物：
  描述：

  甲氧基-二(4-硝基苯氧基)-硫代膦烷 在 enzyme mutant G₆₀A 、 2-环己胺基乙磺酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (S)-Thiophosphoric acid O-methyl ester O'-(4-nitro-phenyl) ester
  参考文献：
  名称：

  Enzymatic Synthesis of Chiral Organophosphothioates from Prochiral Precursors

  摘要：

  The phosphotriesterase from Pseudomonas diminuta has been shown to selectively cleave the pro-R p-nitrophenolate substituent from bis-p-nitrophenyl alkyl phosphothioate esters. When the alkyl substituent is methyl, ethyl, or isopropyl the enantiomeric excess of the product is >/=99%. Manipulation of the active site through mutagenesis has enabled the preparation of protein variants that preferentially hydrolyze the pro-S substituent of the target substrates. This methodology thus permits the preparation of chiral products from prochiral precursors.

  DOI：

  10.1021/ja017840d
• 作为产物：
  描述：

  甲醇 、 O,O,O-三(4-硝基苯基)硫代磷酸酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 甲氧基-二(4-硝基苯氧基)-硫代膦烷
  参考文献：
  名称：

  Enzymatic Synthesis of Chiral Organophosphothioates from Prochiral Precursors

  摘要：

  The phosphotriesterase from Pseudomonas diminuta has been shown to selectively cleave the pro-R p-nitrophenolate substituent from bis-p-nitrophenyl alkyl phosphothioate esters. When the alkyl substituent is methyl, ethyl, or isopropyl the enantiomeric excess of the product is >/=99%. Manipulation of the active site through mutagenesis has enabled the preparation of protein variants that preferentially hydrolyze the pro-S substituent of the target substrates. This methodology thus permits the preparation of chiral products from prochiral precursors.

  DOI：

  10.1021/ja017840d

文献信息

• Hilgetag et al., Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4> 8, p. 207,215
  作者：Hilgetag et al.

  DOI：——

  日期：——
• Gupta, R L; Roy, N K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 334 - 337
  作者：Gupta, R L、Roy, N K

  DOI：——

  日期：——
• Some p-Nitrophenyl Derivatives of o-Phosphoric and o-thiophosphoric Acid
  作者：J. A. A. Ketelaar、H. R. Gersmann

  DOI：10.1021/ja01168a532

  日期：1950.12
• Enzymatic Synthesis of Chiral Organophosphothioates from Prochiral Precursors
  作者：Wen-Shan Li、Yingchun Li、Craig M. Hill、Karin T. Lum、Frank M. Raushel

  DOI：10.1021/ja017840d

  日期：2002.4.1

  The phosphotriesterase from Pseudomonas diminuta has been shown to selectively cleave the pro-R p-nitrophenolate substituent from bis-p-nitrophenyl alkyl phosphothioate esters. When the alkyl substituent is methyl, ethyl, or isopropyl the enantiomeric excess of the product is >/=99%. Manipulation of the active site through mutagenesis has enabled the preparation of protein variants that preferentially hydrolyze the pro-S substituent of the target substrates. This methodology thus permits the preparation of chiral products from prochiral precursors.