tert-butyl 1′-methoxycarbonylferrocene-1-carbamate | 443983-81-1

• 英文名称: tert-butyl 1′-methoxycarbonylferrocene-1-carbamate
• 英文别名: tert-butyl-1′-methoxycarbonyl-1-ferrocenecarbamate；tert-butyl-1'-methoxycarbonyl-1-ferrocenecarbamate；Boc-NH-Fc-COOMe；Boc-Fca-OMe
• CAS: 443983-81-1
• 化学式: C₁₇H₂₁FeNO₄
• 分子量: 359.205
• InChiKey: CYCSBJDCWAWBAV-UHFFFAOYSA-N

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：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  tert-butyl 1′-methoxycarbonylferrocene-1-carbamate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1'-((tert-butoxycarbonyl)amino)ferrocene-1-carboxylic acid
  参考文献：
  名称：

  1'-氨基二茂铁-1-羧酸和脯氨酸的结合物：合成、构象分析和生物学评价

  摘要：

  我们之前的研究表明，二肽 Y-Fca-Ala-OMe (III) 转变为 Y-Ala-Fca-OMe (IV)（Y = Ac，Boc；Fca = 1'-aminoferrocene-1-羧酸）显着影响它们的构象空间。新的生物偶联物 Y-Fca-Pro-OMe (1, Y = Ac; 2, Y = Boc) 和 Y-Pro-Fca-OMe (3, Y = Boc; 4, Y = Ac)研究脯氨酸（一种众所周知的转角诱导剂）对具有交换组成氨基酸序列的小有机金属肽的构象特性的影响。为此，肽 1-4 在溶液中进行了详细的光谱分析（IR、NMR、CD 光谱）。测定了固态中肽 3 的构象。此外，

  DOI：

  10.3390/molecules190812852
• 作为产物：
  描述：

  methyl 1'-azidocarbonylferrocene-1-carboxylate 、 叔丁醇 以 叔丁醇 为溶剂， 以9%的产率得到dimethyl 1',1'-ureylenedi(1-ferrocenecarboxylate)
  参考文献：
  名称：

  Electronic communication through the ureylene bridge: spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi(1-ferrocenecarboxylate)

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2004.04.016

文献信息

• The first oxalamide-bridged ferrocene: Facile synthesis, preliminary conformational analysis and biological evaluation
  作者：Veronika Kovač、Kristina Radošević、Anica Bebek、Janja Makarević、Zoran Štefanić、Lidija Barišić、Mladen Žinić、Vladimir Rapić

  DOI：10.1002/aoc.3653

  日期：2017.7

  so‐obtained oxalamide‐bridged ferrocene 2 was elucidated using infrared and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopies, crystal structure analysis, and electrospray ionization and high‐resolution mass spectrometry. The preliminary conformational analysis in solution suggested the intramolecular engagement of oxalamide protons, while single‐crystal analysis revealed an intermolecular hydrogen‐bonding

  对叔丁基1'-甲氧基羰基-1-二茂铁氨基甲酸酯（1）进行Boc脱保护，得到游离胺，该胺经过草酰氯介导的二聚作用。使用红外光谱和NMR（1 H，13 C，COSY，NOESY，HSQC，HMBC）光谱学，晶体结构分析以及电喷雾电离和高分辨率质谱对得到的草酰胺桥二茂铁2的结构进行了阐明。溶液中的初步构象分析表明草酰胺的质子在分子内参与，而单晶分析揭示了分子间的氢键模式。另外，草酰胺桥二茂铁2的作用对三种人类细胞系（HEK293T，HeLa和HepG2）的细胞活力进行了测试。体外筛选显示，在所应用的浓度范围（1-350μM）中，测试化合物对HEK293T和HepG2细胞具有增殖和细胞毒性作用。正常HEK293T细胞对细胞生长的刺激作用最为明显，而对HeLa肿瘤细胞的细胞毒性作用最高，且呈剂量依赖性。观察到的双重生物活性2暗示其在药物开发中的潜在应用。
• Adamantyl ferrocene derivatives: Antioxidant abilities and effects on model lipid membranes
  作者：Adela Štimac、Jasmina Lapić、Valentino Blasina、Marija Lukinac、Senka Djaković、Ivo Crnolatac、Leo Frkanec、Ruža Frkanec

  DOI：10.1002/aoc.4042

  日期：2018.2

  A series of homoannularly and heteroannularly substituted adamantyl ferrocene derivatives has been synthesized and their effects on membrane fluidity were investigated using liposomes as the membrane models. The liposome formulations of adamantyl ferrocene derivatives were characterized by using dynamic light scattering, differential scanning calorimetry and fluorescence anisotropy measurements. It

  合成了一系列同环和异环取代的金刚烷基二茂铁衍生物，并以脂质体为膜模型研究了它们对膜流动性的影响。金刚烷基二茂铁衍生物的脂质体制剂通过使用动态光散射，差示扫描量热法和荧光各向异性测量来表征。已证明掺入脂质体中的金刚烷基二茂铁衍生物显着影响脂质双层的结构。研究结果表明，金刚烷基二茂铁衍生物化合物9 – 12进入膜的疏水/亲水界面，导致膜流动性显着降低。用DPPH法对合成化合物的抗氧化能力进行了评估，结果表明所检测的化合物具有一定的抗氧化活性。
• Conformational Switching of Multi-Responsive Ferrocenyl-Phenol Conjugates
  作者：Andreas Neidlinger、Christoph Förster、Katja Heinze

  DOI：10.1002/ejoc.201600774

  日期：2016.10

  Multifunctional conformational switches based on the ferrocenyl-salicylic acid amide motif with increasing additional complexity at the Fc moiety (R = COOMe, CONHEt, CONHFc; H-2–H-4; Fc = ferrocenyl) have been prepared and their preferred secondary structures in solution have been elucidated by NMR and IR spectroscopy in combination with conformational searches based on DFT calculations. Their distinct

  基于二茂铁基-水杨酸酰胺基序的多功能构象开关在 Fc 部分（R = COOMe、CONHEt、CONHFc；H-2-H-4；Fc = 二茂铁基）增加了额外的复杂性，并且它们优选的二级结构在已通过核磁共振和红外光谱结合基于 DFT 计算的构象搜索阐明了解决方案。它们对去质子化 ([2]––[4]–) 和氧化 ([H-2]+·–[H-4]+·) 的独特构象响应已通过红外、EPR 和紫外/可见光谱揭示为以及通过 DFT 计算。去质子化反转所有酰胺单元（双酰胺扭曲），而氧化选择性地翻转末端酰胺单元（单酰胺扭曲）。还探索了去质子化和氧化的联合作用。
• Reactions of 1-amino-n′-ferrocenemethylcarboxylate with electrophiles: A combined synthetic, electrochemical, and theoretical study
  作者：Mohammad A.K. Khan、Donald S. Thomas、Heinz-Bernhard Kraatz

  DOI：10.1016/j.ica.2006.04.038

  日期：2006.7

  The reactivity of 1-amino-n'-ferrocenemethylcarboxylate, 1,n'-H2N-Fc-COOCH3 (2) toward alkylating agents is reported and MeNH-Fc-COOMe (3), EtNH-Fc-COOMe (4), EtSCH2CH2NH-Fc-COOMe (5), (EtO)(2)P(O)NH-Fc-COOMe (6) are synthesized by reacting 2 with MeI, EtI, EtSCH2CH2Cl and (CN)(EtO)(2)P(O), respectively. Cyclic voltammetry of these compounds shows different half-wave potential characteristics compared to aminoferrocene and is dependent on the nature of the substituents, which is rationalized by molecular orbital calculations. (c) 2006 Elsevier B.V. All rights reserved.
• Ferrocene compounds: methyl 1′-aminoferrocene-1-carboxylate
  作者：Christoph Förster、Daniel Siebler、Katja Heinze

  DOI：10.1107/s0108270110025746

  日期：2010.9.15

  The title compund, [Fe(C(5)H(6)N)(C(7)H(7)O(2))], features one strong intermolecular hydrogen bond of the type N-H...O=C [N...O = 3.028 (2) A] between the amine group and the carbonyl group of a neighbouring molecule, and vice versa, to form a centrosymmetric dimer. Furthermore, the carbonyl group acts as a double H-atom acceptor in the formation of a second, weaker, hydrogen bond of the type C-H...O=C [C...O = 3.283 (2) A] with the methyl group of the ester group of a second neighbouring molecule at (x, -y - 1/2, z - 1/2). The methyl group also acts as a weak hydrogen-bond donor, symmetry-related to the latter described C-H...O=C interaction, to a third molecule at (x, -y - 1/2, z + 1/2) to form a two-dimensional network. The cyclopentadienyl rings of the ferrocene unit are parallel to each other within 0.33 (3) degrees and show an almost eclipsed 1,1'-conformation, with a relative twist angle of 9.32 (12) degrees . The ester group is twisted slightly [11.33 (8) degrees ] relative to the cylopentadienyl plane due to the above-mentioned intermolecular hydrogen bonds of the carbonyl group. The N atom shows pyramidal coordination geometry, with the sum of the X-N-Y angles being 340 (3) degrees .