methyl (S)-2-methoxycarbonylaminomethyl-2-phenyloxypropanoate | 1022223-86-4

• 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 (S)-2-methoxycarbonylaminomethyl-2-phenyloxypropanoate
• 英文别名: methyl (2S)-3-(methoxycarbonylamino)-2-methyl-2-phenoxypropanoate
• CAS: 1022223-86-4
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: SYUSIUYPFCANBU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-methoxycarbonylaminomethyl-2-phenyloxypropanoate 在 盐酸 作用下， 反应 12.0h， 以94%的产率得到(S)-2-aminomethyl-2-phenyloxypropanoic acid hydrochloride
  参考文献：
  名称：

  Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles

  摘要：

  Although the chemoselectivity problems in substitution reactions, which arise from the use of oxygenated nucleophiles in a basic medium by generating anionic species are well-known, we report herein a highly chemoselective ring-opening reaction of hindered cyclic sulfamidates with O-nucleophiles. The reaction occurs with the inversion of configuration at the quaternary centre, allowing the stereoselective synthesis of an important class of beta(2,2)-amino acids, namely O-substituted alpha-methylisoserines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.030
• 作为产物：
  描述：

  sodium phenoxide 、 dimethyl (R)-5-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazolidine-3,5-dicarboxylate 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 以94%的产率得到methyl (S)-2-methoxycarbonylaminomethyl-2-phenyloxypropanoate
  参考文献：
  名称：

  Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles

  摘要：

  Although the chemoselectivity problems in substitution reactions, which arise from the use of oxygenated nucleophiles in a basic medium by generating anionic species are well-known, we report herein a highly chemoselective ring-opening reaction of hindered cyclic sulfamidates with O-nucleophiles. The reaction occurs with the inversion of configuration at the quaternary centre, allowing the stereoselective synthesis of an important class of beta(2,2)-amino acids, namely O-substituted alpha-methylisoserines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.030

文献信息

• Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles
  作者：Gonzalo Jiménez-Osés、Alberto Avenoza、Jesús H. Busto、Jesús M. Peregrina

  DOI：10.1016/j.tetasy.2008.01.030

  日期：2008.3

  Although the chemoselectivity problems in substitution reactions, which arise from the use of oxygenated nucleophiles in a basic medium by generating anionic species are well-known, we report herein a highly chemoselective ring-opening reaction of hindered cyclic sulfamidates with O-nucleophiles. The reaction occurs with the inversion of configuration at the quaternary centre, allowing the stereoselective synthesis of an important class of beta(2,2)-amino acids, namely O-substituted alpha-methylisoserines. (C) 2008 Elsevier Ltd. All rights reserved.