2-Benzyloxycarbonylamino-2-diethyloxyphosphoryl-essigsaeure-ethylester | 83026-99-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Benzyloxycarbonylamino-2-diethyloxyphosphoryl-essigsaeure-ethylester
• 英文别名: N-Benzyloxycarbonyl-2-(diethoxyphosphinyl)-glycine ethyl ester；ethyl 2-benzyloxycarbonylamino-2-(diethoxyphosphinyl)-acetate；Ethyl 2-benzyloxycarbonylamino-2-(diethoxyphosphoryl)acetate；Ethyl 2-benzyloxycarbonylamino-2-diethoxyphosphorylacetate；Ethyl 2-(((benzyloxy)carbonyl)amino)-2-(diethoxyphosphoryl)acetate；ethyl 2-diethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate
• CAS: 83026-99-7
• 化学式: C₁₆H₂₄NO₇P
• 分子量: 373.343
• InChiKey: OZBQRVNDIMNQBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  511.0±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Benzyloxycarbonylamino-2-diethyloxyphosphoryl-essigsaeure-ethylester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到2-Benzyloxycarbonylamino-2-(diethoxyphosphinyl)-acetic acid
  参考文献：
  名称：

  Amino Acids and Peptides; XLIII¹. Dehydroamino Acids; XVIII². Synthesis of Dehydroamino Acids and Amino Acids fromN-Acyl-2-(dialkyloxyphosphinyl)-glycin Esters; II

  摘要：

  DOI：

  10.1055/s-1984-30730
• 作为产物：
  描述：

  {[(苄氧基)羰基]氨基}(羟基)乙酸 在 硫酸 、 三氯化磷 作用下， 生成 2-Benzyloxycarbonylamino-2-diethyloxyphosphoryl-essigsaeure-ethylester
  参考文献：
  名称：

  Schmidt, Ulrich; Lieberknecht, Albrecht; Schanbacher, Ute, Angewandte Chemie, 1982, vol. 94, # 10, p. 797 - 798

  摘要：

  DOI：

文献信息

• Horner Synthesis of Didehydroamino Acid Derivatives in a Liquid-Liquid Two-Phase System
  作者：Pier Giuseppe Ciattini、Enrico Morera、Giorgio Ortar

  DOI：10.1055/s-1988-27493

  日期：——

  Horner olefination of aldehydes 1 with N-acyl-2-(diethoxyphosphoryl) glycin ethyl esters 2 to give didehydroamino acid derivatives 3 can be performed advantageously in a 20% aqueous sodium hydroxide/dichloromethane two-phase system in the absence of any typical phase-transfer catalyst.

  Horner-Emmons 烯化反应利用 N-酰基-2-(二乙氧基磷酰基)甘氨酸乙酯 2 与醛 1 反应，在无需典型相转移催化剂的情况下，可以优势地在 20% 氢氧化钠水溶液/二氯甲烷两相体系中进行，得到二脱氢氨基酸衍生物 3。
• N–H insertion reactions of rhodium carbenoids. Part 2. Preparation of N-substituted amino(phosphoryl)acetates (N-substituted phosphorylglycine esters)
  作者：Leigh Ferris、David Haigh、Christopher J. Moody

  DOI：10.1039/p19960002885

  日期：——

  Rhodium(II) acetate-catalysed reaction of ethyl 2-diazo-2-diethoxyphosphorylacetate 2 with carbamates, amides, ureas or anilines gives a range of N-substituted 2-amino-2-diethoxyphosphorylacetates 3–18 by N-H insertion reaction of the intermediate rhodium carbenoid.

  乙酸铑（II）催化2-重氮-2-二乙氧基磷酰乙酸乙酯2与氨基甲酸酯，酰胺，脲或苯胺的反应，通过中间体的NH插入反应，可得到一系列N取代的2-氨基-2-二乙氧基磷酰乙酸3–18。铑类胡萝卜素。
• Diastereoselective hydrogenation of monodehydro enkephalins controlled by chiral rhodium catalysts
  作者：A. Hammadi、J.M. Nuzillard、J.C. Poulin、H.B. Kagan

  DOI：10.1016/s0957-4166(00)82083-2

  日期：1992.10

  Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized. These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes. Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides. Strong stereocontrol could be achieved by suitable choice of the chiral catalyst. This method has good potential for stereospecific labelling of enkephalins and other small peptides.