(R)-2-azido-2-phenylacetamide

• 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: (R)-2-azido-2-phenylacetamide
• 英文别名: (R)-2-azido-2-phenyl-acetamide；(2R)-2-azido-2-phenylacetamide
• 化学式: C₈H₈N₄O
• 分子量: 176.178
• InChiKey: WXXGOFFWEFRULL-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester 、 (R)-2-azido-2-phenylacetamide 在 吡啶 作用下， 生成 (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester
  参考文献：
  名称：

  ORALLY ACTIVE CEPHALOGLYCIN ESTERS

  摘要：

  本文介绍了头卤霉素乙酰氧甲基酯和新戊酰氧甲基酯的制备方法。这些酯类能很好地被胃肠道吸收，吸收后会被酶分解，释放出头孢霉素。因此，后者在血液和组织中的含量很高。

  DOI：

  10.7164/antibiotics.24.767
• 作为产物：
  描述：

  (+)-α-azidophenylacetoamide 在 manganese(II) sulfate 、 E. coli DH5α 、 pTrpLAP cells 作用下， 以 水 为溶剂， 生成 (2S)-azidophenylacetic acid 、 (R)-叠氮基苯基乙酸 、 (R)-2-azido-2-phenylacetamide
  参考文献：
  名称：

  Enzymatic and chiral HPLC resolution of α-azido acids and amides

  摘要：

  For the first time, enzymatic resolution of alpha-azido acid amides has been successfully demonstrated with high yields and enantiomeric excess. In one case dynamic kinetic resolution was achieved leading to more than 50% yield of the enantiomerically pure azido acid. Chiral HPLC was also used to separate racemic alpha-azido acids and the separation process was automated. Two routes to enantiopure alpha-azido acid building blocks for solid-phase peptide synthesis have, therefore, been established. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00043-4

文献信息

• Enzymatic and chiral HPLC resolution of α-azido acids and amides
  作者：Christian W Tornøe、Theo Sonke、Ilse Maes、Hans E Schoemaker、Morten Meldal

  DOI：10.1016/s0957-4166(00)00043-4

  日期：2000.3

  For the first time, enzymatic resolution of alpha-azido acid amides has been successfully demonstrated with high yields and enantiomeric excess. In one case dynamic kinetic resolution was achieved leading to more than 50% yield of the enantiomerically pure azido acid. Chiral HPLC was also used to separate racemic alpha-azido acids and the separation process was automated. Two routes to enantiopure alpha-azido acid building blocks for solid-phase peptide synthesis have, therefore, been established. (C) 2000 Elsevier Science Ltd. All rights reserved.
• ORALLY ACTIVE CEPHALOGLYCIN ESTERS
  作者：E. BINDERUP、W. O. GODTFREDSEN、K. ROHOLT

  DOI：10.7164/antibiotics.24.767

  日期：——

  The preparation of the acetoxymethyl and pivaloyloxymethyl esters of cephaloglycin is described. These esters are well absorbed from the gastrointestinal tract and after the absorption are cleaved enzymatically with the liberation of cephaloglycin. As a result high blood- and tissue-levels of the latter are attained.

  本文介绍了头卤霉素乙酰氧甲基酯和新戊酰氧甲基酯的制备方法。这些酯类能很好地被胃肠道吸收，吸收后会被酶分解，释放出头孢霉素。因此，后者在血液和组织中的含量很高。