methyl 1'-azidocarbonylferrocene-1-carboxylate | 443983-73-1

• 英文名称: methyl 1'-azidocarbonylferrocene-1-carboxylate
• 英文别名: 1'-azidocarbonylferrocene-1-methylcarboxylate
• CAS: 443983-73-1
• 化学式: C₁₃H₁₁FeN₃O₃
• 分子量: 313.096
• InChiKey: CKEHORLZTKIFAA-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  methyl 1'-azidocarbonylferrocene-1-carboxylate 以 苯 为溶剂， 生成 methyl 1'-isocyanatoferrocene-1-carboxylate
  参考文献：
  名称：

  Structural, Spectroscopic, and Theoretical Study of Ferrocene Ureidopeptides

  摘要：

  Ferrocene ureidopeptides 3 and 4 and their derivatives 7 and 8 with a methyl ester substituent in 1' position of the ferrocene have been prepared starting from ferrocenecarboxazide (1) or methyl 1'-azidocarbonylferrocene-1-carboxylate (5) via the corresponding isocyanatoferrocenes (2/6) and their coupling with alanine and alanylalanine methyl esters. Thorough spectroscopic and theoretical analyses revealed that in systems 4, 7, and 8 intramolecular hydrogen bonds play only a minor role, while self-assembly processes prevail in solution and in the solid state with urea NH groups acting a hydrogen donors and alanine amide and alanine ester CO groups acting as hydrogen acceptors. The ester substituent in the 1' position of the ferrocene in compounds 7 and 8 does not engage in hydrogen bonding.

  DOI：

  10.1021/om700950r
• 作为产物：
  描述：

  1'-methoxycarbonylferrocene-1-carboxylicacid 、 sodium azide 在 NEt₃ 、 ethyl chloroformate 作用下， 以 水 、 丙酮 为溶剂， 以73%的产率得到methyl 1'-azidocarbonylferrocene-1-carboxylate
  参考文献：
  名称：

  Structural, Spectroscopic, and Theoretical Study of Ferrocene Ureidopeptides

  摘要：

  Ferrocene ureidopeptides 3 and 4 and their derivatives 7 and 8 with a methyl ester substituent in 1' position of the ferrocene have been prepared starting from ferrocenecarboxazide (1) or methyl 1'-azidocarbonylferrocene-1-carboxylate (5) via the corresponding isocyanatoferrocenes (2/6) and their coupling with alanine and alanylalanine methyl esters. Thorough spectroscopic and theoretical analyses revealed that in systems 4, 7, and 8 intramolecular hydrogen bonds play only a minor role, while self-assembly processes prevail in solution and in the solid state with urea NH groups acting a hydrogen donors and alanine amide and alanine ester CO groups acting as hydrogen acceptors. The ester substituent in the 1' position of the ferrocene in compounds 7 and 8 does not engage in hydrogen bonding.

  DOI：

  10.1021/om700950r

文献信息

• Structure of heteroannularly disubstituted ferrocene derivatives containing acetamido group
  作者：Mario Cetina、Senka Djaković、Mojca Čakić Semenčić、Vladimir Rapić

  DOI：10.1016/j.molstruc.2008.10.039

  日期：2009.2

  fully characterized. X-ray single crystal analysis showed that acetamido group in 2 and 4, methoxycarbonyl group in 2 and 6 and azidocarbonyl group in 4 are coplanar with adjacent cyclopentadienyl rings. In compound 6 acetamido group is perpendicular with respect to the plane of the cyclopentadienyl ring. In 2 and 6 ferrocene cyclopentadienyl rings adopt eclipsed conformation, while in 4 they deviate

  1-(乙酰氨基)二茂铁-1-羧酸甲酯(2)、1'-乙酰氨基二茂铁-1-甲酰肼(4)和1'-(1-乙酰氨基乙基)二茂铁-1-羧酸甲酯(6)已制备并充分表征。X射线单晶分析表明，2和4中的乙酰胺基、2和6中的甲氧基羰基和4中的叠氮羰基与相邻的环戊二烯基环共面。在化合物6中，乙酰氨基垂直于环戊二烯基环的平面。在 2 和 6 二茂铁环戊二烯基环中采用重叠构象，而在 4 中它们仅略微偏离这种构象。2和6的分子通过一个N-H····O分子间氢键自组装成无限长链，而衍生物4中的N-H·和··O氢键形成中心对称二聚体。在稀释溶液中测得的 1H NMR 和 IR 光谱表明，乙酰胺酯 2 以游离形式存在，6 含有分子内氢键构象异构体，并伴有少量开放形式。此外，乙酰氨基-叠氮化物 4 的分子在相同条件下是非氢键合的，并且在浓溶液中它们是自组装的。
• Electronic communication through the ureylene bridge: spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi(1-ferrocenecarboxylate)
  作者：Khaled Mahmoud、Yi-Tao Long、Gabriele Schatte、Heinz-Bernhard Kraatz

  DOI：10.1016/j.jorganchem.2004.04.016

  日期：2004.7

  Dimethyl 1',1'-ureylenedi(1-ferrocenecarboxylate) (1) formed during the synthesis of 1-amino, 1'-ferrocenecarboxylic acid shows virtual molecular centrosymmetry. Electronic coupling between the two Fc groups through the ureylene bridge results in both Fc groups being individually oxidizable (DeltaE(1/2) much greater than 0.14 V). The possible existence of intermolecular electronic communication has discussed. The oxidation was followed by spectroelectrochernistry. The separation between the two halfwave potentials DeltaE(1/2) = 137 +/- 5 mV and the comproportionation constant K-c = 207. (C) 2004 Elsevier B.V. All rights reserved.