(S)-methyl 3-(4-(benzylthio)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate | 1609192-58-6

• 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: (S)-methyl 3-(4-(benzylthio)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate
• 英文别名: methyl (2S)-3-(4-benzylsulfanylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1609192-58-6
• 化学式: C₂₂H₂₇NO₄S
• 分子量: 401.527
• InChiKey: XXGFKMSEQNPSOY-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氯化苄 、 (2S)-3-(4-氨基苯基)-2-[(叔丁氧基羰基)氨基]丙酸甲酯 在 2,2'-联吡啶 、 copper(ll) sulfate pentahydrate 、 sodium thiosulfate pentahydrate 、 亚硝酸特丁酯 作用下， 以 甲醇 、 水 为溶剂， 反应 6.67h， 以73%的产率得到(S)-methyl 3-(4-(benzylthio)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate
  参考文献：
  名称：

  A Highly Efficient Cu-Catalyzed S-Transfer Reaction: From Amine to Sulfide

  摘要：

  A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.

  DOI：

  10.1021/ol5009747

文献信息

• A Highly Efficient Cu-Catalyzed S-Transfer Reaction: From Amine to Sulfide
  作者：Yiming Li、Jiahua Pu、Xuefeng Jiang

  DOI：10.1021/ol5009747

  日期：2014.5.16

  A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.