ethyl 2-azidocarbonyl-1-methyl-(1R,2R)-cyclopropane-1-carboxylate | 316363-46-9

• 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: ethyl 2-azidocarbonyl-1-methyl-(1R,2R)-cyclopropane-1-carboxylate
• CAS: 316363-46-9
• 化学式: C₈H₁₁N₃O₃
• 分子量: 197.194
• InChiKey: BWVRFZYNIFGGRI-YLWLKBPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  92.13
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-azidocarbonyl-1-methyl-(1R,2R)-cyclopropane-1-carboxylate 、 苯甲醇 以 甲苯 为溶剂， 反应 1.5h， 生成 ethyl 2-benzyloxycarbonylamino-1-methyl-(1R,2R)-cyclopropane-1-carboxylate
  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
• 作为产物：
  描述：

  ethyl 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylprop-2-enoate 在 盐酸 、 ruthenium(IV) oxide 、 sodium perchlorate 、 氯甲酸乙酯 作用下， 以 乙醇 、 水 为溶剂， 生成 ethyl 2-azidocarbonyl-1-methyl-(1R,2R)-cyclopropane-1-carboxylate
  参考文献：
  名称：

  二苯基脯氨醇甲硅烷基醚催化α-取代的α,β-烯醛的不对称硝基环丙烷化用于构建全碳四元立体中心

  摘要：

  发现二苯基脯氨醇甲硅烷基醚介导的 α-取代的 α,β-不饱和醛与溴硝基甲烷的不对称硝基环丙烷化，然后是碱促进的异构化，可提供具有全碳四元立体中心的反式硝基环丙烷甲醛，具有优异的非对映选择性和对映选择性。DFT 计算表明亚胺离子中间体的 s-反式构象异构体比 s-顺式构象异构体更稳定。此外，计算出溴硝基甲烷阴离子对亚胺离子中间体的亲核攻击优先发生在吡咯烷亚胺中间体的大取代基的相反侧。

  DOI：

  10.1002/ejoc.201500838