Methyl 2,2-dioxo-5-(2-phenylethyl)oxathiazolidine-3-carboxylate | 1189195-95-6

• 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 2,2-dioxo-5-(2-phenylethyl)oxathiazolidine-3-carboxylate
• CAS: 1189195-95-6
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: FLBZUGWJCZEAPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2,2-dioxo-5-(2-phenylethyl)oxathiazolidine-3-carboxylate 在 benzyltriethylammonium tetrathiomolybdate 、 柠檬酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到
  参考文献：
  名称：

  Synthesis of amino thiols and isocysteines via regioselective ring opening of sulfamidates with tetrathiomolybdate

  摘要：

  Herein we present a simple and highly efficient method for the synthesis of beta and gamma-amino thiols via regioselective ring opening of sulfamidates with tetrathiomolybdate 1. The generality of this methodology has been shown by synthesizing carbohydrate derived beta-amino thiol. The scope and versatility of this methodology has been demonstrated by synthesizing biologically important unnatural amino acids like isocysteines in optically pure form. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.074
• 作为产物：
  描述：

  伯吉斯试剂 、 4-phenylbutane-1,2-diol 以 四氢呋喃 为溶剂， 反应 6.0h， 以85%的产率得到Methyl 2,2-dioxo-5-(2-phenylethyl)oxathiazolidine-3-carboxylate
  参考文献：
  名称：

  通过氨基磺酸酯衍生的叠氮基炔烃轻松地进入三唑融合杂环

  摘要：

  通过用叠氮化钠使氨基磺酸盐开环，然后进行一锅炔丙基化和环加成反应制得标题化合物，由多种氨基磺酸盐直接合成缩合三唑。一般而言，该方法论已在衍生自氨基酸，氨基酸衍生物和碳水化合物的多种氨基磺酸盐上得到了证明，从而获得了多种由三唑稠合而成的支架。在一个实例中，已经通过使磺酰胺酯衍生物与炔丙基胺开环合成了含氨基酸的稠合三唑。

  DOI：

  10.1021/jo9016748

文献信息

• Facile Entry into Triazole Fused Heterocycles via Sulfamidate Derived Azido-alkynes
  作者：V. Sai Sudhir、N. Y. Phani Kumar、R. B Nasir Baig、Srinivasan Chandrasekaran

  DOI：10.1021/jo9016748

  日期：2009.10.2

  Direct synthesis of condensed triazoles from diverse sulfamidates by ring opening of sulfamidates with sodium azide followed by one-pot propargylation and cycloaddition furnished title compounds. The methodology in general has been demonstrated on diverse sulfamidates derived from amino acids, amino acid derivatives, and carbohydrates to obtain diverse triazole fused scaffolds. In one example, a condensed

  通过用叠氮化钠使氨基磺酸盐开环，然后进行一锅炔丙基化和环加成反应制得标题化合物，由多种氨基磺酸盐直接合成缩合三唑。一般而言，该方法论已在衍生自氨基酸，氨基酸衍生物和碳水化合物的多种氨基磺酸盐上得到了证明，从而获得了多种由三唑稠合而成的支架。在一个实例中，已经通过使磺酰胺酯衍生物与炔丙基胺开环合成了含氨基酸的稠合三唑。
• Synthesis of amino thiols and isocysteines via regioselective ring opening of sulfamidates with tetrathiomolybdate
  作者：R.B. Nasir Baig、N.Y. Phani Kumar、Jamsad Mannuthodikayil、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2011.02.074

  日期：2011.4

  Herein we present a simple and highly efficient method for the synthesis of beta and gamma-amino thiols via regioselective ring opening of sulfamidates with tetrathiomolybdate 1. The generality of this methodology has been shown by synthesizing carbohydrate derived beta-amino thiol. The scope and versatility of this methodology has been demonstrated by synthesizing biologically important unnatural amino acids like isocysteines in optically pure form. (C) 2011 Elsevier Ltd. All rights reserved.