methyl 5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate | 442537-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate
• 英文别名: 5-[(N-boc-amino)methyl] pyrrole-2-carboxylic acid methyl ester；methyl 5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-1H-pyrrole-2-carboxylate
• CAS: 442537-65-7
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: OKBATSLAEFWDIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 tert-butyl N-[[5-[[3-[[5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-1H-pyrrole-2-carbonyl]amino]phenyl]carbamoyl]-1H-pyrrol-2-yl]methyl]carbamate
  参考文献：
  名称：

  含吡咯的无环受体的合成及阴离子识别性能

  摘要：

  一系列新的无环的阴离子受体（的1 - 4）的基础上的5-（氨基甲基）-1 ħ吡咯-2-羧酸甲酯，设计并合成。这些受体的阴离子识别特性通过1 H NMR光谱检查，并通过密度泛函理论计算合理化。受体1对阴离子客体显示出最高的亲和力和选择性，这主要归因于分子内氢键和刚性分子的几何形状。

  DOI：

  10.1016/j.tet.2007.05.054
• 作为产物：
  描述：

  吡咯-2-羧酸 在 sodium tetrahydroborate 、 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 methyl 5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Development of 5-(aminomethyl)pyrrole-2-carboxylic acid as a constrained surrogate of Gly-ΔAla and its application in peptidomimetic studies

  摘要：

  A new peptidomimetic scaffold based on 5-(aminomethyl)pyrrole-2-carboxylic acid (1) is developed for the first time and used as a conformationally constrained surrogate of the Gly-DeltaAla dipeptide isostere (2) to prepare peptides 3 and 4. (C) 2002 Published by Elsevier Science.

  DOI：

  10.1016/s0040-4039(02)00342-8

文献信息

• Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase
  作者：Dustin D. Hawker、Richard B. Silverman

  DOI：10.1016/j.bmc.2012.08.009

  日期：2012.10

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.
• Effective receptors for fluoride and acetate ions: synthesis and binding study of pyrrole- and cystine-based cyclopeptido-mimetics
  作者：Yanhua Zhang、Zhenming Yin、Jiaqi He、Jin-Pei Cheng

  DOI：10.1016/j.tetlet.2007.06.066

  日期：2007.8

  Two conformationally constrained pseudo-cyclopeptides (1, 2) consisting of pyrrole-, pyridine-, and cystine-moieties were designed and synthesized as neutral receptors for anionic guests. The anion recognition abilities of these two receptors were examined photometrically in acetonitrile solution. The UV-vis study revealed that the [1+1] receptor (1) formed 1:1 complexes with anions, whereas the [2+2] receptor (2) led to 1:2 mode binding with anions. Both receptors displayed good affinity and selectivity for fluoride and acetate ions. (C) 2007 Elsevier Ltd. All rights reserved.
• Development of 5-(aminomethyl)pyrrole-2-carboxylic acid as a constrained surrogate of Gly-ΔAla and its application in peptidomimetic studies
  作者：Tushar K Chakraborty、B Krishna Mohan、S Kiran Kumar、Ajit C Kunwar

  DOI：10.1016/s0040-4039(02)00342-8

  日期：2002.4

  A new peptidomimetic scaffold based on 5-(aminomethyl)pyrrole-2-carboxylic acid (1) is developed for the first time and used as a conformationally constrained surrogate of the Gly-DeltaAla dipeptide isostere (2) to prepare peptides 3 and 4. (C) 2002 Published by Elsevier Science.
• Synthesis and anion recognition properties of pyrrole-bearing acyclic receptors
  作者：Yanhua Zhang、Zhenming Yin、Zucheng Li、Jiaqi He、Jin-Pei Cheng

  DOI：10.1016/j.tet.2007.05.054

  日期：2007.8

  A new series of acyclic anion receptors (1–4) based on methyl 5-(aminomethyl)-1H-pyrrole-2-carboxylate were designed and synthesized. The anion recognition properties of these receptors were examined by 1H NMR spectroscopy and rationalized by density functional theoretical calculation. Receptor 1 displays the highest affinity and selectivity for anionic guests mainly due to the intramolecular hydrogen

  一系列新的无环的阴离子受体（的1 - 4）的基础上的5-（氨基甲基）-1 ħ吡咯-2-羧酸甲酯，设计并合成。这些受体的阴离子识别特性通过1 H NMR光谱检查，并通过密度泛函理论计算合理化。受体1对阴离子客体显示出最高的亲和力和选择性，这主要归因于分子内氢键和刚性分子的几何形状。