N-(2-thiophen-2-ylacetyl)-L-serine methyl ester | 1227951-19-0

• 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: N-(2-thiophen-2-ylacetyl)-L-serine methyl ester
• 英文别名: methyl (2S)-3-hydroxy-2-[(2-thiophen-2-ylacetyl)amino]propanoate
• CAS: 1227951-19-0
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: HWKNLTXMXBVISQ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-thiophen-2-ylacetyl)-L-serine methyl ester 、 5-(1-hydroxy-2-(naphthalen-1-yl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 ammonium molybdate 、 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 5.25h， 以71%的产率得到(3S)-7-(naphthalen-1-ylmethyl)-5-oxo-8-(thiophen-2-yl)-2,3-dihydro-5H-oxazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Improved procedure for the enantioselective synthesis of dihydrooxazolo and dihydrothiazolo ring-fused 2-pyridones

  摘要：

  Improved procedures to synthesize enantioselectively analogues of a peptidomimetic scaffold with high biological relevance have been developed. Experimental design led to a general method for the preparation of dihydrooxazolo ring-fused 2-pyridones in good yields and high enantiomeric purity. The knowledge gained from this was also used to improve the microwave-accelerated synthesis of dihydrothiazolo ring-fused 2-pyridones to give complete stereo retention and high yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.162
• 作为产物：
  描述：

  2-噻吩乙酰氯 、 L-丝氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到N-(2-thiophen-2-ylacetyl)-L-serine methyl ester
  参考文献：
  名称：

  Improved procedure for the enantioselective synthesis of dihydrooxazolo and dihydrothiazolo ring-fused 2-pyridones

  摘要：

  Improved procedures to synthesize enantioselectively analogues of a peptidomimetic scaffold with high biological relevance have been developed. Experimental design led to a general method for the preparation of dihydrooxazolo ring-fused 2-pyridones in good yields and high enantiomeric purity. The knowledge gained from this was also used to improve the microwave-accelerated synthesis of dihydrothiazolo ring-fused 2-pyridones to give complete stereo retention and high yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.162