methyl (1'-amino)ferrocenecarboxylic acid | 206275-03-8

• 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: methyl (1'-amino)ferrocenecarboxylic acid
• 英文别名: methyl 1'-aminoferrocene-1-carboxylate；1-amino-n'-ferrocenemethylcarboxylate；1-amino-1'-ferrocene carboxylic acid methyl ester；cyclopenta-2,4-dien-1-amine;iron(2+);methyl cyclopenta-1,3-diene-1-carboxylate
• CAS: 206275-03-8
• 化学式: C₁₂H₁₃FeNO₂
• 分子量: 259.088
• InChiKey: MDWFQRKUYFQHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1'-amino)ferrocenecarboxylic acid 、 9-fluorenylmethyloxocarbonyl-1-amino-1'-ferrocene carboxylic acid 在 1-chloro-N,N-2-trimethyl-1-propenylamine 、 Zn 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到
  参考文献：
  名称：

  二茂铁氨基酸对氧化还原反应的有机金属折叠剂：固相合成，二级结构和混合价性质†

  摘要：

  寡二茂铁 Fmoc - Fca n - OMe（n = 3–5）以逐步精确的方式从Fmoc受保护 二茂铁氨基酸Fmoc - Fca - OH（^ h - FCA - OH = 1-氨基-1'-二茂铁羧酸; Fmoc = 9-芴基甲氧基羰基）依次通过固体支持物上的酰胺键Fmoc脱保护，酸活化和偶联步骤。生成的定义明确的低聚物在其中形成有序的锯齿形结构四氢呋喃 具有特征的解决方案 氢粘接模式。电化学实验揭示了个体的顺序氧化二茂铁这些肽中的单位会产生混合价阳离子。光学间隔电子转移是通过近红外中的间隔跃迁来检测的。

  DOI：

  10.1039/c0dt01528h
• 作为产物：
  描述：

  tert-butyl 1′-methoxycarbonylferrocene-1-carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (1'-amino)ferrocenecarboxylic acid
  参考文献：
  名称：

  多响应二茂铁-苯酚共轭物的构象转换

  摘要：

  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。

  DOI：

  10.1002/ejoc.201600774

文献信息

• The synthesis and characterisation of heterosubstituted aminoferrocenes
  作者：Ian R Butler、Scott C Quayle

  DOI：10.1016/s0022-328x(97)00528-7

  日期：1998.2

  The synthesis of 1-bromo-1′-aminoferrocene is reported using a simple synthetic methodology. This compound serves as a useful precursor to other heterosubstituted aminoferrocenes. For example, (1′-amino)ferrocenecarboxylic acid has been obtained and is conveniently isolated in its C-protected form by lithiation of 1-bromo-1′-aminoferrocene, quenching with solid carbon dioxide and esterification of

  使用简单的合成方法报道了1-溴-1'-氨基二茂铁的合成。该化合物用作其他杂取代的氨基二茂铁的有用前体。例如，已经获得了（1'-氨基）二茂铁羧酸，并且通过1-溴-1'-氨基二茂铁的锂化，用固体二氧化碳淬灭并用甲醇的HCl将所得的羧酸酯化而方便地以其C-保护的形式分离出（1'-氨基）二茂铁羧酸。 。还使用类似的方法获得了新的配体1-二苯基膦基-1'-氨基二茂铁。
• Ferrocene tripeptide Gly-Pro-Arg conjugates: Synthesis and inhibitory effects on Alzheimer’s Aβ1–42 fibrillogenesis and Aβ-induced cytotoxicity in vitro
  作者：Binbin Zhou、Chun-Lan Li、Yuan-Qiang Hao、Muya Chabu Johnny、You-Nian Liu、Juan Li

  DOI：10.1016/j.bmc.2012.11.030

  日期：2013.1

  Alzheimer's disease (AD) is the most common cause of dementia, and currently there is no clinical treatment to cure it or to halt its progression. Aggregation and fibril formation of beta-amyloid peptides (A beta) are central events in the pathogenesis of AD. Many efforts have been spent on the development of effective inhibitors to prevent A beta fibrillogenesis and cause disaggregation of preformed A beta fibrils. In this study, the conjugates of ferrocene and Gly-Pro-Arg (GPR) tripeptide, Boc-Gly-Pro-Arg(NO2)-Fca-OMe (4, GPR-Fca) and Fc-Gly-Pro-Arg-OMe (7, Fc-GPR) (Fc: ferrocene; Fca: ferrocene amino acid) were synthesized by HOBT/HBTU protocol in solution. These ferrocene GPR conjugates were employed to inhibit A beta(1-42) fibrillogenesis and to disaggregate preformed A beta fibrils. The inhibitory properties of ferrocene GPR conjugates on A beta(1-42) fibrillogenesis were evaluated by thioflavin T (ThT) fluorescence assay, and confirmed by atomic force microscopy (AFM) analysis. The interaction between the ferrocene GPR conjugates and A beta(1-42) was monitored by electrochemical means. Our results showed that both GPR and GPR-Fca can significantly inhibit the fibril formation of A beta(1-42), and cause disaggregation of the preformed fibrils. As expected, GPR-Fca shows stronger inhibitory effect on A beta(1-42) fibrillogenesis than that of its parent peptide GPR. In contrast, Fc-GPR shows no inhibitory effect on fibrillogenesis of A beta(1-42). Furthermore, GPR-Fca demonstrates significantly protection against A beta-induced cytotoxicity and exhibits high resistance to proteolysis and good lipophilicity. (C) 2012 Elsevier Ltd. 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 .