Methyl 2-(N-((4S)-4-(1,1-dimethylethyl)-2-oxazolidinone-3-carbamoyl))aminoacetate | 154657-00-8

• 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: Methyl 2-(N-((4S)-4-(1,1-dimethylethyl)-2-oxazolidinone-3-carbamoyl))aminoacetate
• 英文别名: methyl 2-[[(4S)-4-tert-butyl-2-oxo-1,3-oxazolidine-3-carbonyl]amino]acetate
• CAS: 154657-00-8
• 化学式: C₁₁H₁₈N₂O₅
• 分子量: 258.274
• InChiKey: AIBUFYWAAMTDHR-SSDOTTSWSA-N

物化性质

• 密度：
  1.229±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-(N-((4S)-4-(1,1-dimethylethyl)-2-oxazolidinone-3-carbamoyl))aminoacetate 在 N-溴代丁二酰亚胺(NBS) 、 zinc chloride diethyl ether 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 Methyl 2-(N-((4S)-4-(1,1-dimethylethyl)-2-oxazolidinone-3-carbamoyl)amino)-4-pentenoate
  参考文献：
  名称：

  Radical Reaction Initiated and Stereocontrolled by Zinc Chloride

  摘要：

  The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5a) was accelerated at -50 degrees C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78 degrees C in the presence of ZnCl2 . OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2 . OEt2, the reaction afforded methyl (2R)-2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3- carbamoyl)amino]4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2 . OEt2 works as a radical initiator as well as chelating agent.

  DOI：

  10.3987/com-97-s(n)71
• 作为产物：
  描述：

  (S)-(?)-4-叔丁基-2-噁唑烷酮 在 sodium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 Methyl 2-(N-((4S)-4-(1,1-dimethylethyl)-2-oxazolidinone-3-carbamoyl))aminoacetate
  参考文献：
  名称：

  Radical Reaction Initiated and Stereocontrolled by Zinc Chloride

  摘要：

  The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5a) was accelerated at -50 degrees C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78 degrees C in the presence of ZnCl2 . OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2 . OEt2, the reaction afforded methyl (2R)-2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3- carbamoyl)amino]4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2 . OEt2 works as a radical initiator as well as chelating agent.

  DOI：

  10.3987/com-97-s(n)71

文献信息

• Yamamoto, Yoshinori; Onuki, Setsuko; Yumoto, Masatoshi, Journal of the American Chemical Society, 1994, vol. 116, # 1, p. 421 - 422
  作者：Yamamoto, Yoshinori、Onuki, Setsuko、Yumoto, Masatoshi、Asao, Naoki

  DOI：——

  日期：——
• Radical Reaction Initiated and Stereocontrolled by Zinc Chloride
  作者：Yoshinori Yamamoto、Setsuko Onuki、Masatoshi Yumoto、Naoki Asao

  DOI：10.3987/com-97-s(n)71

  日期：——

  The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5a) was accelerated at -50 degrees C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78 degrees C in the presence of ZnCl2 . OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2 . OEt2, the reaction afforded methyl (2R)-2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3- carbamoyl)amino]4-pentenoate 6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2 . OEt2 works as a radical initiator as well as chelating agent.