(1R,2S)-2-[((1R,2S)-2-Benzyloxycarbonylamino-cyclobutanecarbonyl)-amino]-cyclobutanecarboxylic acid methyl ester | 517913-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (1R,2S)-2-[((1R,2S)-2-Benzyloxycarbonylamino-cyclobutanecarbonyl)-amino]-cyclobutanecarboxylic acid methyl ester
• 英文别名: (1R,2S)-methyl 2-((1R,2S)-2-(benzyloxycarbonylamino)cyclobutanecarboxamido)cyclobutanecarboxylate；methyl (1R,2S)-2-[[(1R,2S)-2-(phenylmethoxycarbonylamino)cyclobutanecarbonyl]amino]cyclobutane-1-carboxylate
• CAS: 517913-91-6
• 化学式: C₁₉H₂₄N₂O₅
• 分子量: 360.41
• InChiKey: KOBVCLORGCSZKP-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-[((1R,2S)-2-Benzyloxycarbonylamino-cyclobutanecarbonyl)-amino]-cyclobutanecarboxylic acid methyl ester 在 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  Self-Assembly of a Cyclobutane β-Tetrapeptide To Form Nanosized Structures

  摘要：

  A beta-tetrapeptide made up of homochiral cyclobutane residues displays conformational bias in solution prompted by the formation of intramolecular hydrogen bonds. Moreover, this compound self-assembles to produce nanosized fibrils and, in some media, it also forms a gel. The combination of NMR, TEM, AFM, and theoretical calculations has proven to be very useful in obtaining insight into the details of these new structures.

  DOI：

  10.1021/ol701521k
• 作为产物：
  描述：

  methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 20.0h， 生成 (1R,2S)-2-[((1R,2S)-2-Benzyloxycarbonylamino-cyclobutanecarbonyl)-amino]-cyclobutanecarboxylic acid methyl ester
  参考文献：
  名称：

  Stereodivergent syntheses of the first bis(cyclobutane) β-dipeptides

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00652-3

文献信息

• (+)- and (−)-2-Aminocyclobutane-1-carboxylic Acids and Their Incorporation into Highly Rigid β-Peptides:  Stereoselective Synthesis and a Structural Study
  作者：Sandra Izquierdo、Federico Rúa、Abdelouahid Sbai、Teodor Parella、Ángel Álvarez-Larena、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1021/jo0510843

  日期：2005.9.1

  Several derivatives of (+)- and (−)-2-aminocyclobutane-1-carboxylic acid, 1, have been prepared through enantiodivergent synthetic sequences. The stereoselective synthesis of free amino acid (+)-1 has been achieved, and this product has been fully characterized for the first time. Stereocontrolled alternative synthetic methodologies have been developed for the preparation of bis(cyclobutane) β-dipeptides

  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。
• 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.
• Self-Assembly of a Cyclobutane β-Tetrapeptide To Form Nanosized Structures
  作者：Federico Rúa、Stéphanie Boussert、Teodor Parella、Ismael Díez-Pérez、Vicenç Branchadell、Ernest Giralt、Rosa M. Ortuño

  DOI：10.1021/ol701521k

  日期：2007.8.1

  A beta-tetrapeptide made up of homochiral cyclobutane residues displays conformational bias in solution prompted by the formation of intramolecular hydrogen bonds. Moreover, this compound self-assembles to produce nanosized fibrils and, in some media, it also forms a gel. The combination of NMR, TEM, AFM, and theoretical calculations has proven to be very useful in obtaining insight into the details of these new structures.