methyl 3-[(3-methyl-4-nitrobenzyl)sulfanyl]propanoate | 1185886-59-2

• 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 3-[(3-methyl-4-nitrobenzyl)sulfanyl]propanoate
• 英文别名: Methyl 3-[(3-methyl-4-nitrophenyl)methylsulfanyl]propanoate
• CAS: 1185886-59-2
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: VGXFTHMREPBSSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-[(3-methyl-4-nitrobenzyl)sulfanyl]propanoate 在 sodium tungstate dihydrate 、 双氧水 、 四丁基硫酸氢铵 作用下， 以 水 、 甲苯 为溶剂， 以5.85 kg的产率得到methyl 3-[(3-methyl-4-nitrobenzyl)sulfonyl]propanoate
  参考文献：
  名称：

  Remote Electronic Control in the Regioselective Reduction of Succinimides: A Practical, Scalable Synthesis of EP4 Antagonist MF-310

  摘要：

  A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic-properties of a remote pyridine ring, preparation of cyclopropane carboxylic acid 3 via a Corey-Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5.

  DOI：

  10.1021/jo901267x
• 作为产物：
  描述：

  3-巯基丙酸甲酯 、 3-甲基-4-硝基苄溴 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 生成 methyl 3-[(3-methyl-4-nitrobenzyl)sulfanyl]propanoate
  参考文献：
  名称：

  Remote Electronic Control in the Regioselective Reduction of Succinimides: A Practical, Scalable Synthesis of EP4 Antagonist MF-310

  摘要：

  A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic-properties of a remote pyridine ring, preparation of cyclopropane carboxylic acid 3 via a Corey-Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5.

  DOI：

  10.1021/jo901267x