Monoethyl propylphosphonite | 104902-88-7

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: Monoethyl propylphosphonite
• 英文别名: ethyl propyl-H-phosphinate；ethyl propylphosphinate；1-[Ethoxy(oxido)phosphaniumyl]propane；1-[ethoxy(oxido)phosphaniumyl]propane
• CAS: 104902-88-7
• 化学式: C₅H₁₃O₂P
• 分子量: 136.131
• InChiKey: LTNFJAVMUXTDTH-UHFFFAOYSA-N

物化性质

• 沸点：
  88 °C(Press: 10 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Monoethyl propylphosphonite 在 盐酸 、 四(三苯基膦)钯 、 三乙胺 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 ethyl (4-{[6-(3-nitrophenyl)pyrimidin-4-yl]amino}phenyl)propylphosphinate
  参考文献：
  名称：

  Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors

  摘要：

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.

  DOI：

  10.1021/jm401742r
• 作为产物：
  描述：

  diethyl propylphosphonite 在 盐酸 作用下， 以 水 为溶剂， 以73%的产率得到Monoethyl propylphosphonite
  参考文献：
  名称：

  Convenient One Pot Synthesis of Phosphonites and H-Phosphinates

  摘要：

  A convenient and simple one-pot method is described for the synthesis of phosphonites [RP(OEt)(2), 1] and H-phosphinates [HP(O)R(OEt), 2] from triethyl phosphite and appropriate Grignard reagents.

  DOI：

  10.1081/scc-120018928

文献信息

• Synthesis of α-aminophosphinates by the hydrophosphinylation of imines
  作者：Andrea Szabó、Imre Petneházy、Zsuzsa M. Jászay

  DOI：10.1002/hc.10133

  日期：——

  Numerous substituted α-aminophosphinates were synthesized by addition of alkyl and phenyl H-phosphinates to aromatic imines and characterized. Modest diastereoselectivity was observed in the reaction. The size of the substituents exerts a small effect on the diastereoselectivity of PC bond formation. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:235–240, 2003; Published online in Wiley InterScience

  许多取代的 α-氨基次膦酸盐是通过将烷基和苯基 H-次膦酸盐加成到芳族亚胺上来合成并表征的。在反应中观察到适度的非对映选择性。取代基的大小对 PC 键形成的非对映选择性影响很小。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:235–240, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10133
• Phosphinic Acid Analogs of GABA. 2. Selective, Orally Active GABAB Antagonists
  作者：Wolfgang Froestl、Stuart J. Mickel、Georg von Sprecher、Peter J. Diel、Roger G. Hall、Ludwig Maier、Dietrich Strub、Vito Melillo、Peter A. Baumann

  DOI：10.1021/jm00017a016

  日期：1995.8

  In 1987, 25 years after the synthesis of the potent and selective GABA(B) agonist baclofen (1), Kerr et al.(5) described the first GABA(B) antagonist phaclofen 2. However, phaclofen and structurally similar derivatives 3-5 did not cross the blood-brain barrier and hence were inactive in vivo as central nervous system agents. As a consequence, the therapeutic potential of GABA(B) antagonists remained unclear. In exploring GABA and baclofen derivatives by replacing the carboxylic acid residue with various phosphinic acid groups, we discovered more potent and water soluble GABA(B) antagonists. Electrophysiological experiments in vivo demonstrated that some of the new compounds were capable of penetrating the blood-brain barrier after oral administration. Neurotransmitter release experiments showed that they interacted with several presynaptic GABA(B) receptor subtypes, enhancing the release of GABA, glutamate, aspartate, and somatostatin. The new GABA(B) antagonists interacted also with postsynaptic GABA(B) receptors, as they blocked late inhibitory postsynaptic potentials. They facilitated the induction of long-term potentiation in vitro and in, vivo, suggesting potential cognition enhancing effects. Fifteen compounds were investigated in Various memory and learning paradigms in rodents. Although several compounds were found to be active, only 10 reversed the age-related deficits of old rats in a multiple-trial one-way active avoidance test after chronic treatment. The cognition facilitating effects of 10 were confirmed in learning experiments in Rhesus monkeys. The novel GABA(B) antagonists showed also protective effects in various animal models of absence epilepsy.
• Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors
  作者：Gábor Németh、Zoltán Greff、Anna Sipos、Zoltán Varga、Rita Székely、Mónika Sebestyén、Zsuzsa Jászay、Szabolcs Béni、Zoltán Nemes、Jean-Luc Pirat、Jean-Noël Volle、David Virieux、Ágnes Gyuris、Katalin Kelemenics、Éva Áy、Janos Minarovits、Susan Szathmary、György Kéri、László Őrfi

  DOI：10.1021/jm401742r

  日期：2014.5.22

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.
• Convenient One Pot Synthesis of Phosphonites and H-Phosphinates
  作者：Imre Petneházy、Zsuzsa M. Jászay、Andrea Szabó、Kinga Everaert

  DOI：10.1081/scc-120018928

  日期：2003.1.6

  A convenient and simple one-pot method is described for the synthesis of phosphonites [RP(OEt)(2), 1] and H-phosphinates [HP(O)R(OEt), 2] from triethyl phosphite and appropriate Grignard reagents.