甲基(1R,2S)-2-氨基环丁烷羧酸酯 | 221158-94-7

• 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
• 中文名称: 甲基(1R,2S)-2-氨基环丁烷羧酸酯
• 中文别名: (1R,2S)-2-氨基环丁烷-1-羧酸甲酯；2-[3-[4-(苯甲酰氨基)-2,5-二甲氧苯基]-1-甲基三氮烯基-2-基]乙磺化钠
• 英文名称: methyl 2-amino-(1R,2S)-cyclobutane-1-carboxylate
• 英文别名: methyl (1R,2S)-2-aminocyclobutane-1-carboxylate
• CAS: 221158-94-7
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: IMHXOVKGKHSNDO-UHNVWZDZSA-N

物化性质

• 沸点：
  169.1±33.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基(1R,2S)-2-氨基环丁烷羧酸酯 在 palladium dihydroxide 氢气 作用下， 生成 5-氨基戊酸甲酯
  参考文献：
  名称：

  （+）-和（-）-2-氨基环丁烷-1-羧酸及其掺入高刚性β-肽的立体选择性合成和结构研究

  摘要：

  通过对映异构的合成序列已经制备了（+）-和（-）-2-氨基环丁烷-1-羧酸1的几种衍生物。立体选择性合成游离氨基酸（+）- 1已实现，并且此产品已首次全面表征。已经开发了立体控制的替代合成方法以高产率制备双（环丁烷）β-二肽。其中，已经合成了对映体和非对映体。还已经制备了由环丁烷残基和线性氨基酸的偶联产生的β，β-和β，δ-二聚体。已经显示出环丁烷环作为单体和二聚体中的结构促进单元的能力。NMR结构研究和DFT理论计算证明了强分子内分子的形成氢键产生顺式[4.2.0]辛烷结构单元，在溶液和气相中均赋予这些分子高刚性。还观察到了由围绕氨基甲酸酯NC（O）键旋转引起的顺式-反式构象平衡的贡献，反式是主要的构象体。在固态中，不存在该平衡，此外，存在分子间氢键。

  DOI：

  10.1021/jo0510843
• 作为产物：
  描述：

  methyl hydrogen (-)-(1R,2S)-cyclobutane-1,2-dicarboxylate 在 palladium on activated charcoal 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 50.0 ℃ 、202.65 kPa 条件下， 反应 6.5h， 生成 甲基(1R,2S)-2-氨基环丁烷羧酸酯
  参考文献：
  名称：

  Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: synthesis and structural study of a conformationally constrained β-dipeptide

  摘要：

  Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane beta -amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded beta -amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-beta -amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00297-4

文献信息

• [EN] 1 H-PYRAZOLO[4,3-G]ISOQUINOLINE AND 1 H-PYRAZOLO[4,3-G]QUINOLINE DERIVATIVES AS ALPHA-1 -ANTITRYPSIN MODULATORS FOR TREATING ALPHA-1 -ANTITRYPSIN DEFICIENCY (AATD)<br/>[FR] DÉRIVÉS DE 1H-PYRAZOLO [4,3-G] ISOQUINOLÉINE ET DE 1H-PYRAZOLO [4,3-G] QUINOLÉINE EN TANT QUE MODULATEURS D'ALPHA-1-ANTITRYPSINE POUR TRAITER UNE DÉFICIENCE EN ALPHA-1-ANTITRYPSINE (AATD)
  申请人：VERTEX PHARMA

  公开号：WO2021203025A1

  公开（公告）日：2021-10-07

  1H-pyrazolo[4,3-g]isoquinoline and 1H-pyrazolo[4,3-g]quinoline derivatives as alpha-1-antitrypsin modulators for treating alpha-1- antitrypsin deficiency (AATD).

  1H-吡唑并[4,3-g]异喹啉和1H-吡唑并[4,3-g]喹啉衍生物作为α-1-抗胰蛋白酶调节剂，用于治疗α-1-抗胰蛋白酶缺乏症（AATD）。
• [EN] 7- OR 8-HYDROXY-ISOQUINOLINE AND 7- OR 8-HYDROXY-QUINOLINE DERIVATIVES AS ALPHA-1 -ANTITRYPSIN MODULATORS FOR TREATING ALPHA-1 -ANTITRYPSIN DEFICIENCY (AATD)<br/>[FR] DÉRIVÉS DE 7-OU 8-HYDROXY-ISOQUINOLÉINE ET DE 7-OU 8-HYDROXY-QUINOLÉINE EN TANT QUE MODULATEURS D'ALPHA-1-ANTITRYPSINE POUR TRAITER UNE DÉFICIENCE EN ALPHA-1-ANTITRYPSINE (AATD)
  申请人：VERTEX PHARMA

  公开号：WO2021203028A1

  公开（公告）日：2021-10-07

  7- or 8-hydroxy-isoquinoline and 7- or 8-hydroxy-quinoline derivatives as alpha-l-antitrypsin modulators for treating alpha-l-antitrypsin deficiency (AATD).

  7-或8-羟基异喹啉和7-或8-羟基喹啉衍生物作为治疗α-1-抗胰蛋白酶缺乏症（AATD）的α-1-抗胰蛋白酶调节剂。
• Prevalence of Eight-Membered Hydrogen-Bonded Rings in Some Bis(cyclobutane) β-Dipeptides Including Residues with Trans Stereochemistry
  作者：Elisabeth Torres、Esther Gorrea、Eric Da Silva、Pau Nolis、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1021/ol900636w

  日期：2009.6.4

  Three new bis(cyclobutane) beta-dipeptides have been synthesized from appropriate derivatives of cis- and trans-2-aminocyclobutane-1-carboxylic acid, respectively. The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)- and (trans,cis)-beta-dipeptides while the formation of six-membered rings is preferred for the (cis,trans)- beta-dipeptide similarly to the previously described (cis,cis)-diastereomer.
• Stereoselective synthesis of (−)-(1R,2S)-2-aminocyclobutane-1-carboxylic acid, a conformationally constrained β-amino acid
  作者：Marta Martı́n-Vilà、Cristina Minguillón、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(98)00462-5

  日期：1998.12

  The title compound as well as some derivatives have been synthesized for the first time in optically active form by means of a chemoenzymatic transformation used to induce asymmetry in achiral precursors. The enantio- and diastereomeric purity has been determined by HPLC and NMR techniques. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereodivergent syntheses of the first bis(cyclobutane) β-dipeptides
  作者：Sandra Izquierdo、Marta Martı́n-Vilà、Albertina G. Moglioni、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(02)00652-3

  日期：2002.11

  The efficient synthesis of methyl 2-benzyloxycarbonylamino-(1S,2R)-cyclobutane-1-carboxylate starting from 2-methoxycarbonyl-(1R,2S)-cyclobutane-1-carboxylic acid is described. This beta-amino acid derivative is antipodal with respect to the (1R,2S)-compound that was previously synthesized in our laboratory from the same chiral hemi ester. In turn, these enantiomeric beta-amino acids have been self-condensed and coupled with one another to provide, respectively, enantiomeric and diastereomeric bis(cyclobutane) beta-dipeptides. These products are the first reported beta-amino acid oligomers containing two directly linked cyclobutane residues. (C) 2002 Elsevier Science Ltd. All rights reserved.