(propan-2-yloxy)(propyl)phosphinoyl chloride | 13213-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (propan-2-yloxy)(propyl)phosphinoyl chloride
• 英文别名: Isopropyl propylphosphonochloridate；propyl-phosphonic acid-chloride isopropyl ester；Propyl-phosphonsaeure-chlorid-isopropylester；Isopropyl-propylphosphonochloridat；Phosphonochloridic acid, propyl-, 1-methylethyl ester；1-[chloro(propan-2-yloxy)phosphoryl]propane
• CAS: 13213-45-1
• 化学式: C₆H₁₄ClO₂P
• 分子量: 184.603
• InChiKey: JNGKJHCEEBDIJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (propan-2-yloxy)(propyl)phosphinoyl chloride 、 L-丙氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以67%的产率得到N-(Methyl-L-alanyl) isopropyl propylphosphonamidate
  参考文献：
  名称：

  The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines

  摘要：

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.

  DOI：

  10.1021/jo00104a016
• 作为产物：
  描述：

  diisopropyl propylphosphonate 在 COCl₂ 作用下， 生成 (propan-2-yloxy)(propyl)phosphinoyl chloride
  参考文献：
  名称：

  587.有机磷化合物的反应性。第四部分 碳酰氯与某些酯的反应

  摘要：

  DOI：

  10.1039/jr9610003067

文献信息

• 587. The reactivity of organophosphorus compounds. Part IV. The reaction of carbonyl chloride with some esters
  作者：J. I. G. Cadogan

  DOI：10.1039/jr9610003067

  日期：——
• Induction of p53 Accumulation by Moloney Murine Leukemia Virus-ts1 Infection in Astrocytes Via Activation of Extracellular Signal-Regulated Kinases 1/2
  作者：Hun-Taek Kim、Serban Tasca、Wenan Qiang、Paul K Y Wong、George Stoica

  DOI：10.1097/01.lab.0000017373.82871.45

  日期：2002.6

  We previously reported that Moloney murine leukemia virus-ts1-mediated neuronal degeneration in mice is likely a result of both loss of glial support and release of cytokines and neurotoxins from ts1-infected glial cells. Viral infection in some cell types regulates expression of p53 protein, a key regulator of cell proliferation and death. Therefore, we hypothesized that p53 and its dependent genes may be linked with ts1-mediated neuropathology. We examined the presence of p53 and its dependent gene product, a proapoptotic protein bax-alpha, in ts1-induced spongiform encephalomyelopathy. Compared with controls, the lesions of infected animals contained increased levels of p53 and bax-a in astrocytes, as shown by strong nuclear p53 and cytoplasmic bax-alpha immunoreactivity in astrocytes. To determine how ts1 affects p53 expression in astrocytes, we then assessed the expression of p53 and its dependent genes, such as bax-alpha and p21, in infected and uninfected immortalized C1 astrocytes and studied possible pathways responsible for p53 accumulation in infected astrocytes. In these studies using mitogen-activated protein kinase inhibitors, infection-induced increases in the p53 level were partially blocked by PD98059, a synthetic inhibitor of MEK1 that is the immediate upstream kinase of extracellular signal-regulated kinases 1/2 (ERK1/2), but not by SB202190, a potent p38 kinase inhibitor. Furthermore, treatment with PD98059 significantly decreased the level of p21 protein, a p53-dependent gene product. These results suggest that ts1 infection may stabilize p53 protein through activation of ERKs in C1 astrocytes, leading to increased expression of the p21 and bax-alpha proteins, both of which induce cell cycle arrest and apoptosis. Our studies suggest that ts1 neuropathology in mice may result from changes in expression and activity of p53, brought about in part by ts1 activation of ERK.
• 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.
• The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines
  作者：William P. Malachowski、James K. Coward

  DOI：10.1021/jo00104a016

  日期：1994.12

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.