benzyl methylphosphonochloridate | 122086-11-7

• 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: benzyl methylphosphonochloridate
• 英文别名: [chloro(methyl)phosphoryl]oxymethylbenzene
• CAS: 122086-11-7
• 化学式: C₈H₁₀ClO₂P
• 分子量: 204.593
• InChiKey: CEMHSILTBJUQTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  277.9±33.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl methylphosphonochloridate 在 钯 氢气 、 二乙醇胺 作用下， 生成 C₁₃H₁₈NO₆P
  参考文献：
  名称：

  Evaluation of phosphorus-containing inhibitors of γ-glutamyl hydrolase

  摘要：

  Several putative, phosphorus-containing inhibitors of gamma-glutamyl hydrolase were synthesized and evaluated for inhibitory activity. The phosphonamidoic acids were shown to be weak competitive inhibitors while both a phosphoramidate diester and a phosphonamidate ester were shown to be potent time-dependent inactivators, presumably through irreversible phosphorylation of an active site nucleophile. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00253-4
• 作为产物：
  描述：

  亚磷酸二苄酯 在 五氯化磷 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 18.5h， 生成 benzyl methylphosphonochloridate
  参考文献：
  名称：

  Synthesis and evaluation of a polyamine phosphinate and phosphonamidate as transition-state analogue inhibitors of spermidine/spermine-N1-acetyltransferase

  摘要：

  Polyamine analogues such as bis(ethyl)norspermine and N-1-ethyl-N-11-[(cyclopropyl)methyl]-4,8-diazaundecane (CPENSpm) act as inhibitors of the enzyme spermidine/spermine-N-1-acetyltransferase (SSAT) in vitro and possess impressive antitumor activity against a number of cell lines. However, the propensity of these compounds to superinduce SSAT in intact cells limits their usefulness in studies aimed at elucidating the role of SSAT in cellular metabolism. The recently synthesized alkylpolyamine analogue N-1-ethyl-N-11-[(cycloheptyl)methyl]-3,8-diazaundecane (CHENSpm, 3) is also an effective inhibitor of SSAT and has potent antitumor activity, but does not appear to superinduce SSAT. These findings suggest that it is possible to synthesize polyamine analogues that can be used for selective inhibition of the enzyme in cellular metabolic studies. Along these lines, the phosphate-based transition state analogues 4 and 5 were synthesized and evaluated as inhibitors of isolated SSAT. Phosphonamidate 4 was rapidly hydrolyzed under the assay conditions, and thus did not inhibit the enzyme. However, the phosphinate analogue 5 was an effective inhibitor of purified human SSAT, with a K, value of 250 mu M. The inhibitory activity of 5 was also compared with that of CHENSpm (IC50 = 13 mu M), as well as a series of bis-substituted alkylpolyamine analogues. The unsymmetrically substituted polyamine analogue CHENSpm (3) and the phosphinate transition state analogue 5 represent the first functional, nonsuperinducing inhibitors of human SSAT. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00072-7

文献信息

• α-Haloenamines as Reagents for the Conversion of Phosphorus Oxyacids to Their Halogenated Analogues
  作者：Rikard Norlin、Lars Juhlin、Per Lind、Lars Trogen

  DOI：10.1055/s-2005-865363

  日期：——

  Phosphorus oxyacids are converted to their halogenated analogues under mild conditions. α-Haloenamines are shown to be effective halogen transfer reagents affording good to high yields of the desir ...

  磷含氧酸在温和条件下转化为它们的卤代类似物。α-卤代烯胺被证明是有效的卤素转移试剂，可提供良好至高产率的所需...
• [EN] PHOSPHONATES SYNTHONS FOR THE SYNTHESIS OF PHOSPHONATES DERIVATIVES SHOWING BETTER BIOAVAILABILITY<br/>[FR] SYNTHONS DE PHOSPHONATES POUR LA SYNTHESE DE DERIVES DE PHOSPHONATES PRESENTANT UNE MEILLEURE BIODISPONIBILITE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2010146127A1

  公开（公告）日：2010-12-23

  Synthons for the synthesis of phosphonates prodrugs POM and POC, especially for direct Cross Metathesis.

  合成磷酸酯前药POM和POC的合成合成子，特别适用于直接交叉烯烃转化。
• Convenient “one-pot” synthesis of chlorophosphonates, chlorophosphates and chlorophosphoramides from the corresponding benzyl esters
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1016/0040-4039(95)00865-a

  日期：1995.7

  Selective monodeprotection of alkyl phosphonate, phosphate and phosphoramide benzyl esters using quinuclidine and chlorination of the subsequent salts allows preparation of various alkyl phosphonochloridates, monochlorophosphates and monochlorophosphoramides in a convenient “one-pot” procedure.

  使用奎尼丁对烷基膦酸酯，磷酸酯和磷酰胺苄基酯进行选择性单脱保护，然后对后续的盐进行氯化，可以方便的“一锅法”制备各种烷基膦酰氯，一氯磷酸酯和一氯磷酰胺。
• PHOSPHONATE COMPOUNDS HAVING IMMUNO-MODULATORY ACTIVITY
  申请人：Cannizzaro Carina

  公开号：US20090227543A1

  公开（公告）日：2009-09-10

  The invention is related to phosphonate substituted compounds having immuno-modulatory activity, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及磷酸酯取代化合物，具有免疫调节活性，含有这种化合物的组合物，以及包括这种化合物的给药的治疗方法，还涉及用于制备这种化合物的有用过程和中间体。
• Antiviral compounds
  申请人：Cai Zhenhong R.

  公开号：US20080076740A1

  公开（公告）日：2008-03-27

  The invention is related to phosphorus substituted anti-viral inhibitory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  该发明涉及磷取代的抗病毒抑制化合物、含有该化合物的组合物、包括给予该化合物的治疗方法，以及用于制备该化合物的有用过程和中间体。