dimethyl (3-nitrophenyl)phosphonate | 89277-94-1

• 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: dimethyl (3-nitrophenyl)phosphonate
• 英文别名: dimethyl 3-nitrophenylphosphonate；3-Nitro-phenylphosphonsaeure-dimethylester；1-Dimethoxyphosphoryl-3-nitrobenzene
• CAS: 89277-94-1
• 化学式: C₈H₁₀NO₅P
• 分子量: 231.145
• InChiKey: YPMHHDNPXMZSFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (3-nitrophenyl)phosphonate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 dimethyl (3-aminophenyl)phosphonate
  参考文献：
  名称：

  Phosphorus analogs of .gamma.-aminobutyric acid, a new class of anticonvulsants

  摘要：

  A series of phosphorus compounds, designed as analogues of gamma-aminobutyric acid (GABA) in that they possess a P = O moiety separated by three atoms from an amino or acetamido group, was synthesized and tested by using in vitro GABAA and GABAB receptor binding, GABA uptake assays, and was examined for anticonvulsant activity. Weak GABAB receptor affinity was noted for one agent, whereas six compounds displayed moderate to high potencies as inhibitors of electroshock- and pentylenetetrazol-induced seizures. The best anticonvulsant effect was found with the (m-aminophenyl) phosphinic acid compounds, with members of this class selected for further study.

  DOI：

  10.1021/jm00371a017
• 作为产物：
  描述：

  3-硝基苯磺酸 在 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 dimethyl (3-nitrophenyl)phosphonate
  参考文献：
  名称：

  Phosphorus analogs of .gamma.-aminobutyric acid, a new class of anticonvulsants

  摘要：

  A series of phosphorus compounds, designed as analogues of gamma-aminobutyric acid (GABA) in that they possess a P = O moiety separated by three atoms from an amino or acetamido group, was synthesized and tested by using in vitro GABAA and GABAB receptor binding, GABA uptake assays, and was examined for anticonvulsant activity. Weak GABAB receptor affinity was noted for one agent, whereas six compounds displayed moderate to high potencies as inhibitors of electroshock- and pentylenetetrazol-induced seizures. The best anticonvulsant effect was found with the (m-aminophenyl) phosphinic acid compounds, with members of this class selected for further study.

  DOI：

  10.1021/jm00371a017

文献信息

• Cobalt Catalyzed C-P Bond Formation by Cross-Coupling of Boronic Acids with P(O)H Compounds in Presence of Zinc
  作者：Ian Hicks、Jonathan McTague、Tatiana Hapatsha、Rania Teriak、Parminder Kaur

  DOI：10.3390/molecules25020290

  日期：——

  In our current work, we have reported the first cobalt-catalyzed cross-coupling of arylboronic acid with alkyl/aryl phosphites under mild conditions. The reaction was carried out in the presence of zinc powder as an additive and ter-pyridine as a ligand. The use of non-precious cobalt salt makes the protocol advantageous, as it is inexpensive and more abundant than the previously used methods where

  在我们目前的工作中，我们报道了在温和条件下首次钴催化芳基硼酸与烷基/芳基亚磷酸酯的交叉偶联。该反应在锌粉作为添加剂和三联吡啶作为配位体的存在下进行。非贵金属钴盐的使用使该协议具有优势，因为它比以前使用的贵金属盐（Pd 和 Pt）的方法便宜且丰富。该反应底物范围广，产物收率良好。
• EP2554165
  申请人：——

  公开号：——

  公开（公告）日：——
• EP2551262
  申请人：——

  公开号：——

  公开（公告）日：——
• ——
  作者：JOSIOKA JOSIKADZU、 XASIBA ISAMU、 TSUTII SYUDZI

  DOI：——

  日期：——
• Phosphorus analogs of .gamma.-aminobutyric acid, a new class of anticonvulsants
  作者：Lindley A. Cates、Ven Shun Li、Chriss C. Yakshe、Michael O. Fadeyi、Terrance H. Andree、Edward W. Karbon、Salvatore J. Enna

  DOI：10.1021/jm00371a017

  日期：1984.5

  A series of phosphorus compounds, designed as analogues of gamma-aminobutyric acid (GABA) in that they possess a P = O moiety separated by three atoms from an amino or acetamido group, was synthesized and tested by using in vitro GABAA and GABAB receptor binding, GABA uptake assays, and was examined for anticonvulsant activity. Weak GABAB receptor affinity was noted for one agent, whereas six compounds displayed moderate to high potencies as inhibitors of electroshock- and pentylenetetrazol-induced seizures. The best anticonvulsant effect was found with the (m-aminophenyl) phosphinic acid compounds, with members of this class selected for further study.