N-(tert-butyloxycarbonyl)-1-amino-2,2-dimethylcyclopropanecarboxylic acid methyl ester | 138571-87-6

• 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: N-(tert-butyloxycarbonyl)-1-amino-2,2-dimethylcyclopropanecarboxylic acid methyl ester
• 英文别名: methyl 2,2-dimethyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 138571-87-6
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: OOSQHDJCKYRYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-1-amino-2,2-dimethylcyclopropanecarboxylic acid methyl ester 在 N-甲基吗啉 、 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(tert-butyloxycarbonyl)-(β-tert-butyl ester)-L-aspartyl-(Z)-1-amino-2,2-dimethylcyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and taste properties of L-aspartyl-methylated 1-aminocyclopropanecarboxylic acid methyl esters

  摘要：

  Several isomers of L-aspartyl-1-aminocyclopropanecarboxylic acid methyl ester with methyl group substitutions on the cyclopropane ring were synthesized. Conformational analyses were carried out on these molecules using H-1 NMR and molecular modeling studies. Their taste properties are explained on the basis of our previously reported topochemical model for taste response.

  DOI：

  10.1021/jo00030a009
• 作为产物：
  描述：

  2-叔丁氧羰基氨基丙烯酸甲酯 以 四氢呋喃 、 乙醚 为溶剂， 生成 N-(tert-butyloxycarbonyl)-1-amino-2,2-dimethylcyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and taste properties of L-aspartyl-methylated 1-aminocyclopropanecarboxylic acid methyl esters

  摘要：

  Several isomers of L-aspartyl-1-aminocyclopropanecarboxylic acid methyl ester with methyl group substitutions on the cyclopropane ring were synthesized. Conformational analyses were carried out on these molecules using H-1 NMR and molecular modeling studies. Their taste properties are explained on the basis of our previously reported topochemical model for taste response.

  DOI：

  10.1021/jo00030a009

文献信息

• Cyclopropane analogue of valine: influence of side chain orientation on peptide folding
  作者：Ana I. Jiménez、Michel Marraud、Carlos Cativiela

  DOI：10.1016/s0040-4039(03)00514-8

  日期：2003.4

  The cyclopropane analogue of valine (1-amino-2,2-dimethylcyclopropanecarboxylic acid, c3Val) has been synthesised and incorporated into the model peptides tBuCO-l-Pro-l-c3Val-NHiPr and tBuCO-l-Pro-d-c3Val-NHiPr. In the solid state, both dipeptides accommodate a type II β-turn stabilised by an NHiPr to tBuCO hydrogen bond. Remarkably, the peptide incorporating l-c3Val also exhibits a distorted γ-turn

  已合成缬氨酸的环丙烷类似物（1-氨基-2,2-二甲基环丙烷羧酸，c 3 Val）并将其掺入模型肽t BuCO-1-Pro-lc 3 Val-NH i Pr和t BuCO-1- Pro-dc 3 Val-NH i Pr。在固态下，两个二肽都具有通过NH i Pr到t BuCO氢键稳定的II型β-转角。引人注目的是，掺有lc 3 Val的肽在环丙烷残基周围也表现出扭曲的γ转角，Pro-CO和NH i Pr分子内氢键。