methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclopropane-1-carboxylate | 53229-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclopropane-1-carboxylate
• 英文别名: rac-methyl (1R,2S)-2-{[(benzyloxy)carbonyl]amino}cyclopropane-1-carboxylate；methyl (1R,2S)-2-(phenylmethoxycarbonylamino)cyclopropane-1-carboxylate
• CAS: 53229-57-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: LDUAAHZTNAGKCO-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醇 、 (+/-)-cis-2-Carbomethoxycyclopropanecarbonyl-chloride 生成 methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclopropane-1-carboxylate
  参考文献：
  名称：

  Ring-opening reactions of certain 2-carbonyl-substituted cyclopropylamines

  摘要：

  DOI：

  10.1021/jo00890a006

文献信息

• Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: synthesis and structural study of a conformationally constrained β-dipeptide
  作者：Marta Martı́n-Vilà、Elena Muray、Gemma P Aguado、Angel Alvarez-Larena、Vicenç Branchadell、Cristina Minguillón、Ernest Giralt、Rosa M Ortuño

  DOI：10.1016/s0957-4166(00)00297-4

  日期：2000.9

  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.
• Ring-opening reactions of certain 2-carbonyl-substituted cyclopropylamines
  作者：Joseph G. Cannon、John E. Garst

  DOI：10.1021/jo00890a006

  日期：1975.1