methyl (2S)-1-[1-(tert-butylamino)-2-methyl-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxylate | 1446348-60-2

• 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 (2S)-1-[1-(tert-butylamino)-2-methyl-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxylate
• CAS: 1446348-60-2
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: NYDKCBFLDYGJDW-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-谷氨酸 1-甲酯 、 异氰酸叔丁酯 、 丙酮 以 甲醇 为溶剂， 反应 26.5h， 以67%的产率得到methyl (2S)-1-[1-(tert-butylamino)-2-methyl-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  A Biomimetic Approach to Terpenes Isolated from Marine Sponges: a Ugi Coupling Reaction in a Hypothetical Biosynthesis

  摘要：

  A unique pathway for the biosynthesis of marine sponge terpenes is proposed. Based on this proposal, a biomimetic approach using a Ugi coupling reaction has been designed and applied to the efficient construction of the right-side, peptide-like portions of boneratamides and exigurin.

  DOI：

  10.1055/s-0032-1318305

文献信息

• A Biomimetic Approach to the Synthesis of Terpene-Amino Acid Conjugates. The Ugi Reaction in the Hypothetical Biosynthesis of Marine Natural Products
  作者：Yoshiyasu Ichikawa、Kenta Saito、Rika Mimura、Ayumi Kitamori、Akihito Matsukawa、Akifumi Ikeda、Toshiya Masuda、Hiyoshizo Kotsuki、Keiji Nakano

  DOI：10.3987/com-16-13442

  日期：——

  A unique pathway for the biosynthesis of the marine sponge terpenes, exigurin and boneratamides A-C, is proposed. Based on this proposal, a biomimetic strategy on key Ugi coupling reactions between terpene isocyanides and amino acids was developed for construction of the core structures of exigurin and boneratamides A-C.