methyl 1-(benzyloxycarbonylamino)benzyl phosphonate

• 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: methyl 1-(benzyloxycarbonylamino)benzyl phosphonate
• 英文别名: methoxy-[phenyl(phenylmethoxycarbonylamino)methyl]phosphinic acid
• 化学式: C₁₆H₁₈NO₅P
• 分子量: 335.296
• InChiKey: FRVTTZKYQCXDDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-(benzyloxycarbonylamino)benzyl phosphonate 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 benzyl N-[[methoxy-[methoxy-[phenyl(phenylmethoxycarbonylamino)methyl]phosphoryl]oxyphosphoryl]-phenylmethyl]carbamate
  参考文献：
  名称：

  A novel and convenient method for synthesizing unsymmetrical N-benzyloxycarbonyl-protected 1-amino-1-arylalkylphosphonate mixed diesters

  摘要：

  利用氨基甲酸苄酯、芳香醛和烷氧基二氯化膦的一锅反应，然后在三乙胺存在下用醇处理，合成了非对称的 N-苄氧羰基保护的 1-氨基-1-芳基烷基膦酸盐混合二酯。31P NMR 对反应进行了跟踪，并提出了一种机理。

  DOI：

  10.1039/b008340m
• 作为产物：
  描述：

  N-benzyloxycarbonyl-1-amino-1-phenylmethanephosphonic acid 2-cyanoethyl monoester 在 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.25h， 生成 methyl 1-(benzyloxycarbonylamino)benzyl phosphonate
  参考文献：
  名称：

  Szewczyk, Jerzy; Rachon, Janusz; Wasielewski, Czeslaw, Polish Journal of Chemistry, 1982, vol. 56, # 3, p. 477 - 483

  摘要：

  DOI：

文献信息

• A Convenient Synthesis of Alkyl Hydrogen 1-(Benzyloxycarbonylamino)-alkanephosphonates
  作者：Maria Hoffmann

  DOI：10.1055/s-1986-31701

  日期：——
• Wasielewski,C. et al., Roczniki Chemii, 1976, vol. 50, p. 1613 - 1620
  作者：Wasielewski,C. et al.

  DOI：——

  日期：——
• Szewczyk, Jerzy; Wasielewski, Czeslaw, Polish Journal of Chemistry, 1981, vol. 55, # 10, p. 1985 - 1994
  作者：Szewczyk, Jerzy、Wasielewski, Czeslaw

  DOI：——

  日期：——
• Inhibition of tRNA-dependent ligase MurM from Streptococcus pneumoniae by phosphonate and sulfonamide inhibitors
  作者：Elena Cressina、Adrian J. Lloyd、Gianfranco De Pascale、B. James Mok、Stephen Caddick、David I. Roper、Christopher G. Dowson、Timothy D.H. Bugg

  DOI：10.1016/j.bmc.2009.03.028

  日期：2009.5

  Ligase MurM catalyses the addition of Ala from alanyl-tRNA(Ala), or Ser from seryl-tRNA(Ser), to lipid intermediate II in peptidoglycan biosynthesis in Streptococcus pneumoniae, and is a determinant of high-level penicillin resistance. Phosphorus-based transition state analogues were designed as inhibitors of the MurM-catalysed reaction. Phosphonamide analogues mimicking the attack of a lysine nucleophile upon Ala-tRNA(Ala) showed no inhibition of MurM, but adenosine 3'-phosphonate analogues showed inhibition of MurM, the most active being a 2'-deoxyadenosine analogue (IC50 100 mu M). Structure/function studies upon this analogue established that modi. cation of the amino group of the aminoalkylphosphonate resulted in loss of potency, and modi. cation of the adenosine 5'-hydroxyl group with either a t-butyl dimethyl silyl or a carbamate functional group resulted in loss of activity. A library of 48 aryl sulfonamides was also screened against MurM using a radiochemical assay, and two compounds showed sub-millimolar inhibition. These compounds are the first small molecule inhibitors of the Fem ligase family of peptidyltransferases found in Gram-positive bacteria. (C) 2009 Elsevier Ltd. All rights reserved.
• A Modified Method for Synthesis of Alkyl Hydrogen α-(Benzyloxycarbonylamino)-benzylphosphonates
  作者：Qing Dai、Ruyu Chen

  DOI：10.1080/00397919708005634

  日期：1997.10

  A series of alkyl hydrogen alpha-(benzyloxycarbonylamino)benzylphosphonates are prepared from benzyl carbamate, substituted benzaldehydes and alkoxydichlorophosphine in acetyl chloride and subsequent hydrolysis. Compared with the previous methods, the reaction avoids producing the corresponding diesters and thus improves the yields of the products.