(S)-4-tert-Butoxycarbonylamino-4-phenylcarbamoyl-butyric acid

• 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)-4-tert-Butoxycarbonylamino-4-phenylcarbamoyl-butyric acid
• 英文别名: (4S)-5-anilino-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: AJRNVYQRILVOAZ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[(3S)-四氢-2,6-二氧代-2H-吡喃-3-基]-氨基甲酸叔丁酯 、 苯胺 以 二甲基亚砜 为溶剂， 反应 0.33h， 生成 (S)-4-tert-Butoxycarbonylamino-4-phenylcarbamoyl-butyric acid 、 (2S)-2-[(tert-butoxycarbonyl)amino]-4-(phenylcarbamoyl)butanoic acid
  参考文献：
  名称：

  Controlled Regioselective Anilide Formation from Aspartic and Glutamic Acid Anhydrides

  摘要：

  The regioselectivity of the reaction of aniline with a series of N-protected aspartic and glutamic acid anhydrides was controlled through the choice of reaction solvent. In benzene, the formation of aspartic or glutamic acid a-anilides was favored, with alpha:(beta or gamma) regioselectivities as high as 100:0. On the other hand, in DMSO, the formation of either aspartic acid beta-anilide or glutamic acid gamma-anilide was favored, with alpha:(beta or gamma) regioselectivities as high as 0:100. This regioselectivity was not observed for alkylamines, amino acids, thiols, or alcohols. However, the high yields of the aniline reactions and the ability to specify their regioselectivities demonstrate the usefulness of our method for the formation of aspartic and glutamic acid anilide bonds.

  DOI：

  10.1021/jo971375e

文献信息

• Controlled Regioselective Anilide Formation from Aspartic and Glutamic Acid Anhydrides
  作者：Xicai Huang、Xuehong Luo、Yoann Roupioz、Jeffrey W. Keillor

  DOI：10.1021/jo971375e

  日期：1997.12.1

  The regioselectivity of the reaction of aniline with a series of N-protected aspartic and glutamic acid anhydrides was controlled through the choice of reaction solvent. In benzene, the formation of aspartic or glutamic acid a-anilides was favored, with alpha:(beta or gamma) regioselectivities as high as 100:0. On the other hand, in DMSO, the formation of either aspartic acid beta-anilide or glutamic acid gamma-anilide was favored, with alpha:(beta or gamma) regioselectivities as high as 0:100. This regioselectivity was not observed for alkylamines, amino acids, thiols, or alcohols. However, the high yields of the aniline reactions and the ability to specify their regioselectivities demonstrate the usefulness of our method for the formation of aspartic and glutamic acid anilide bonds.