2-(5-trifluoracetamidopentoxy)-2-(1,2,2-trimethylpropoxy)-2-methyl-(4,6-di-tert-butyl)-1,3-dioxa-2λ(5)-benzophosphole | 245096-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-(5-trifluoracetamidopentoxy)-2-(1,2,2-trimethylpropoxy)-2-methyl-(4,6-di-tert-butyl)-1,3-dioxa-2λ(5)-benzophosphole
• CAS: 245096-68-8
• 化学式: C₂₈H₄₇F₃NO₅P
• 分子量: 565.654
• InChiKey: OGWSGXSZZCVYEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(5-trifluoracetamidopentoxy)-2-(1,2,2-trimethylpropoxy)-2-methyl-(4,6-di-tert-butyl)-1,3-dioxa-2λ(5)-benzophosphole 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以91%的产率得到2-(5-aminopentoxy)-2-(1,2,2-trimethylpropoxy)-2-methyl-(4,6-di-tert-butyl)-1,3-dioxa-2λ(5)-benzophosphole
  参考文献：
  名称：

  Hydrolysis of Organophosphorus Nerve Agent Soman by the Monoclonal Antibodies Elicited Against an Oxyphosphorane Hapten.

  摘要：

  The antibody-mediated hydrolysis of the nerve agent O-1,2,2-trimethylpropyl methylphosphonofluoridate (soman) 1 has now been established with two monoclonal antibodies raised against the cyclic pentacovalent methyloxyphosphorane hapten 10 that mimics the pentacoordinated trigonal bipyramidal transition-state of the reaction. The hydrolysis reaction was studied using molecular orbital methods at the MP2/6-31 + G*//HF/6-31 + G* level of accuracy. According to the nb initio carculations, the reaction seems to proceed via three separate transition-states. The calculations are in good agreement with the experimental results. The 1,3-dioxabenzophosphole hapten 10 was synthesized, coupled to the carrier protein and the antibodies were obtained by the hybridoma technique. Two antibodies, DB-108P and DB-108Q were found to enhance the rate of soman hydrolysis and they were kinetically characterised.

  DOI：

  10.3891/acta.chem.scand.53-0473
• 作为产物：
  描述：

  3,3-二甲基-2-丁醇 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 67.25h， 生成 2-(5-trifluoracetamidopentoxy)-2-(1,2,2-trimethylpropoxy)-2-methyl-(4,6-di-tert-butyl)-1,3-dioxa-2λ(5)-benzophosphole
  参考文献：
  名称：

  Hydrolysis of Organophosphorus Nerve Agent Soman by the Monoclonal Antibodies Elicited Against an Oxyphosphorane Hapten.

  摘要：

  The antibody-mediated hydrolysis of the nerve agent O-1,2,2-trimethylpropyl methylphosphonofluoridate (soman) 1 has now been established with two monoclonal antibodies raised against the cyclic pentacovalent methyloxyphosphorane hapten 10 that mimics the pentacoordinated trigonal bipyramidal transition-state of the reaction. The hydrolysis reaction was studied using molecular orbital methods at the MP2/6-31 + G*//HF/6-31 + G* level of accuracy. According to the nb initio carculations, the reaction seems to proceed via three separate transition-states. The calculations are in good agreement with the experimental results. The 1,3-dioxabenzophosphole hapten 10 was synthesized, coupled to the carrier protein and the antibodies were obtained by the hybridoma technique. Two antibodies, DB-108P and DB-108Q were found to enhance the rate of soman hydrolysis and they were kinetically characterised.

  DOI：

  10.3891/acta.chem.scand.53-0473