methyl 5-methoxy-3-p-tolylisoxazolidine-5-carboxylate | 873088-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl 5-methoxy-3-p-tolylisoxazolidine-5-carboxylate
• 英文别名: Methyl 5-methoxy-3-(4-methylphenyl)-1,2-oxazolidine-5-carboxylate
• CAS: 873088-22-3
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: YUOGITLSDUMLJG-UHFFFAOYSA-N

物化性质

• 沸点：
  337.2±52.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-methoxy-3-p-tolylisoxazolidine-5-carboxylate 、 苯丙酮酸 以 水 、 叔丁醇 为溶剂， 反应 21.0h， 以92%的产率得到
  参考文献：
  名称：

  Iterative, Aqueous Synthesis of β³-Oligopeptides without Coupling Reagents

  摘要：

  The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.

  DOI：

  10.1021/ja057706j
• 作为产物：
  描述：

  2-甲氧基-2-丙酸甲酯 在 高氯酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 52.0h， 生成 methyl 5-methoxy-3-p-tolylisoxazolidine-5-carboxylate
  参考文献：
  名称：

  Iterative, Aqueous Synthesis of β³-Oligopeptides without Coupling Reagents

  摘要：

  The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.

  DOI：

  10.1021/ja057706j

文献信息

• Amide forming chemical ligation
  申请人：Bode W. Jeffrey

  公开号：US20070060773A1

  公开（公告）日：2007-03-15

  An amide is formed by reacting an α-ketoacid or salt thereof in a decarboxylative condensation reaction with an amine or salt thereof comprising a nitrogen covalently bound to an atom selected from oxygen, nitrogen, and sulfur. The amide bond is formed between the α-carbon of the ketoacid and the nitrogen of the amine. The α-ketoacid can be formed using a novel sulfur reagent.

  酰胺是通过将α-酮酸或其盐与含有氮原子与氧、氮、硫原子中选择的一个原子共价结合的胺或其盐在脱羧缩合反应中反应而形成的。酰胺键形成在酮酸的α-碳和胺的氮之间。α-酮酸可以使用一种新型硫试剂来形成。
• AMIDE FORMING CHEMICAL LIGATION
  申请人：Regents of the University of California

  公开号：EP1924550A1

  公开（公告）日：2008-05-28
• Amide Forming Chemical Ligation
  申请人：Bode Jeffrey W.

  公开号：US20090069536A1

  公开（公告）日：2009-03-12

  An amide is formed by reacting an α-ketoacid or salt thereof in a decarboxylative condensation reaction with an amine or salt thereof comprising a nitrogen covalently bound to an atom selected from oxygen, nitrogen, and sulfur. The amide bond is formed between the α-carbon of the ketoacid and the nitrogen of the amine. The α-ketoacid can be formed using a novel sulfur reagent.
• US7737293B2
  申请人：——

  公开号：US7737293B2

  公开（公告）日：2010-06-15
• US7667076B2
  申请人：——

  公开号：US7667076B2

  公开（公告）日：2010-02-23