(S)-ethyl (1-(allylamino)-3-methyl-1-oxobutan-2-yl)carbamate | 1433416-54-6

• 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)-ethyl (1-(allylamino)-3-methyl-1-oxobutan-2-yl)carbamate
• 英文别名: ethyl N-[(2S)-3-methyl-1-oxo-1-(prop-2-enylamino)butan-2-yl]carbamate
• CAS: 1433416-54-6
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: XWTPAQZVGPAPLU-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘苯二乙酸 、 (S)-ethyl (1-(allylamino)-3-methyl-1-oxobutan-2-yl)carbamate 在 三氟化硼乙醚 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(2-((S)-1-((ethoxycarbonyl)amino)-2-methylpropyl)-4,5-dihydrooxazol-5-yl)methyl acetate
  参考文献：
  名称：

  Iodine(III)-promoted synthesis of oxazolines from N-allylamides

  摘要：

  PhI(OAc)(2) (activated by BF3 center dot OEt2) has been used to promote the oxidative cyclization of N-allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C-O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.140
• 作为产物：
  描述：

  L-缬氨酸 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 23.5h， 生成 (S)-ethyl (1-(allylamino)-3-methyl-1-oxobutan-2-yl)carbamate
  参考文献：
  名称：

  Iodine(III)-promoted synthesis of oxazolines from N-allylamides

  摘要：

  PhI(OAc)(2) (activated by BF3 center dot OEt2) has been used to promote the oxidative cyclization of N-allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C-O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.140

文献信息

• Iodine(III)-promoted synthesis of oxazolines from N-allylamides
  作者：Nicholas G. Moon、Andrew M. Harned

  DOI：10.1016/j.tetlet.2013.03.140

  日期：2013.6

  PhI(OAc)(2) (activated by BF3 center dot OEt2) has been used to promote the oxidative cyclization of N-allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C-O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile. (C) 2013 Elsevier Ltd. All rights reserved.