ortho-ferrocenyl benzoyl ethyl ester | 1294-29-7

• 英文名称: ortho-ferrocenyl benzoyl ethyl ester
• 英文别名: 2-ethoxycarbonylphenylferrocene；ortho-ferrocenyl ethyl benzoate；ethyl ortho-ferrocenylbenzoate；ethyl-2-(ferrocenyl)benzoate
• CAS: 1294-29-7
• 化学式: C₁₉H₁₈FeO₂
• 分子量: 334.198
• InChiKey: JLSDEHQRAPYLNA-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：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  sodium hydroxide 、 ortho-ferrocenyl benzoyl ethyl ester 以 甲醇 为溶剂， 生成 ortho-(ferrocenyl)-benzoic acid
  参考文献：
  名称：

  ñ -邻-Ferrocenyl苯甲酰二肽酯的合成，结构表征和体外的抗癌活性ñ - {邻- （二茂铁基）苯甲酰基}甘氨酸-L-丙氨酸乙酯和ñ - {邻- （二茂铁基）苯甲酰基} -l-丙氨酸-甘氨酸乙酯

  摘要：

  ñ -邻-ferrocenyl苯甲酰二肽酯2 - 6通过制备耦合邻-ferrocenyl苯甲酸1二肽乙酯GlyGly（OET）（2），GlyAla（OET）（3），GlyPhe（OET）（4）， AlaGly（OEt）（5）和AlaPhe（OEt）（6）。通过一系列NMR光谱技术，质谱和循环伏安法对化合物进行了全面表征。已经确定了3和5对肺癌细胞的细胞毒性。

  DOI：

  10.1016/j.jorganchem.2006.10.018
• 作为产物：
  描述：

  二茂铁 、 2-氨基苯甲酸乙酯 在 盐酸 、 sodium nitrite 作用下， 以 not given 为溶剂， 生成 ortho-ferrocenyl benzoyl ethyl ester
  参考文献：
  名称：

  ñ -邻-Ferrocenyl苯甲酰二肽酯的合成，结构表征和体外的抗癌活性ñ - {邻- （二茂铁基）苯甲酰基}甘氨酸-L-丙氨酸乙酯和ñ - {邻- （二茂铁基）苯甲酰基} -l-丙氨酸-甘氨酸乙酯

  摘要：

  ñ -邻-ferrocenyl苯甲酰二肽酯2 - 6通过制备耦合邻-ferrocenyl苯甲酸1二肽乙酯GlyGly（OET）（2），GlyAla（OET）（3），GlyPhe（OET）（4）， AlaGly（OEt）（5）和AlaPhe（OEt）（6）。通过一系列NMR光谱技术，质谱和循环伏安法对化合物进行了全面表征。已经确定了3和5对肺癌细胞的细胞毒性。

  DOI：

  10.1016/j.jorganchem.2006.10.018

文献信息

• The synthesis and structural characterization of N-ortho-ferrocenyl benzoyl amino acid esters. The X-ray crystal structure of N-{ortho-(ferrocenyl)benzoyl}-l-phenylalanine ethyl ester
  作者：David Savage、Gwen Malone、Steven R. Alley、John F. Gallagher、Alok Goel、Paula N. Kelly、Helge Mueller-Bunz、Peter T.M. Kenny

  DOI：10.1016/j.jorganchem.2005.09.019

  日期：2006.1

  A series of N-ortho-ferrocenyl benzoyl amino acid ethyl esters 3–9 have been prepared by coupling ortho-ferrocenyl benzoic acid 2 to the amino acid ethyl esters of glycine, l-alanine, l-leucine, l-phenylalanine, β-alanine, 4-aminobutyric acid and (±)-2-aminobutyric acid using the conventional 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole protocol. The compounds were fully characterized by a

  一系列ñ -邻-ferrocenyl苯甲酰氨基酸乙酯3 - 9已准备由耦合邻-ferrocenyl苯甲酸2至甘氨酸，L-丙氨酸，L-亮氨酸，L-苯丙氨酸的氨基酸乙酯，β-丙氨酸，4-氨基丁酸和（±）-2-氨基丁酸使用常规的1,3-二环己基碳二亚胺，1-羟基苯并三唑方案。通过一系列NMR光谱技术和质谱（MALDI-MS，ESI-MS）对化合物进行了全面表征。已经确定了1-苯丙氨酸衍生物6的X射线晶体结构。
• Palladium-catalyzed cross-coupling reaction of bis(ferrocenyl)mercury with aryl iodides
  作者：Alexey V Tsvetkov、Gennadij V Latyshev、Nikolai V Lukashev、Irina P Beletskaya

  DOI：10.1016/s0040-4039(00)00535-9

  日期：2000.5

  Cross-coupling reactions of bis(ferrocenyl)mercury with aryl- and heteroaryl iodides were shown to be easy and convenient for the synthesis of monoarylsubstituted ferrocenes in high yields. The highly selective substitution of iodine atom in iodobromoarenes by the ferrocenyl unit was demonstrated.

  已显示双（二茂铁基）汞与芳基和杂芳基碘化物的交叉偶联反应对于高产率地合成单芳基取代的二茂铁是容易和方便的。证明了二茂铁基单元对碘溴芳烃中碘原子的高度选择性取代。
• A structural systematic study of semi-rigid ferrocene derivatives as a 3 × 3 metallocene isomer grid: p -/ m -/ o -(FcC 6 H 4 )CONH( p -/ m -/ o -C 6 H 4 )CO 2 Et, [Fc = (η 5 -C 5 H 5 )Fe(η 5 -C 5 H 4 )]
  作者：John F. Gallagher、Steven Alley、Alan J. Lough

  DOI：10.1016/j.ica.2016.01.028

  日期：2016.4

  The nine ethyl 4-/3-/2-[(4-/3-/2-ferrocenylphenyl)carbonyl]amino}benzoates, 4-/3-/2-FcC(6)H(4)-CONH-(4-/3-/2-C6H4)CO2Et, where Fc = (eta(5)-C5H5)Fe(eta(5)-C5H4)} have been synthesised by coupling either the para- ,meta- or ortho(ferrocenyl) benzoic acids (FcC(6)H(4)COOH), or their acid chlorides (FcC(6)H(4)COCl) with ethyl p-/m-/o-aminobenzoates, H2NC6H4CO2Et using (i) 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxy-benzotriazole (HOBt) or (ii) acid chloride coupling reactions. The isomers were characterised by spectroscopic techniques; single crystal X-ray diffraction structures of all nine isomers are reported and reveal the inherent linearity of the para- para substituted isomer (pp) compared to the twisted geometry of the ortho-ortho system (oo). Intra-/intermolecular interactions and distinct patterns of molecular aggregation are evaluated and correlated with physicochemical measurements showing distinct trends. A rich and somewhat congested amide center dot center dot center dot amide hydrogen bonding is noted in (mp) and (mm), contrasting with a lack of amide center dot center dot center dot amide interactions in (pp) and (pm) and unexpected amide center dot center dot center dot ester hydrogen bonding in dimers of (om). The series highlights the unpredictable nature of molecular assembly. (C) 2016 Elsevier B.V. All rights reserved.
• Synthesis, characterization and in vitro anti-cancer activity of N-(ferrocenyl)benzoyl tri- and tetrapeptide esters
  作者：Alan J. Corry、Áine Mooney、Dermot O’Sullivan、Peter T.M. Kenny

  DOI：10.1016/j.ica.2009.01.021

  日期：2009.7

  N-ortho, N-meta and N-para-(ferrocenyl)benzoyl tri- and tetrapeptide esters (2-7) were prepared by coupling ortho, meta and para-ferrocenyl benzoic acids to the tri- and tetrapeptide ethyl esters of GlyGlyGly(OEt) and GlyGlyGlyGly(OEt) in the presence of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole. The compounds were characterized by a range of NMR spectroscopic techniques, mass spectrometry and cyclic voltammetry. The anti-proliferative effects of the ortho derivatives 2 and 5 were measured in vitro against H1299 lung cancer cells and both gave IC50 values greater than 50 mu M. Therefore, extending the length of the peptide chain had a negative effect on activity, relative to N-(ferrocenyl)benzoyl amino acid and dipeptide derivatives. (C) 2009 Elsevier B.V. All rights reserved.
• Bis(ferrocenyl)mercury as a source of ferrocenyl moiety in Pd-catalyzed reactions of carbon–carbon bond formation
  作者：Irina P Beletskaya、Alexei V Tsvetkov、Gennadij V Latyshev、Victor A Tafeenko、Nikolai V Lukashev

  DOI：10.1016/s0022-328x(01)00979-2

  日期：2001.12

  The application of bis(ferrocenyl)mercury as a source of ferrocenyl group in Pd-catalyzed reactions with aryl halides, acid chlorides and electrophilic alkynes has been demonstrated. The formation of dimethyl-(Z)-2,3-di(ferrocenyl)-2-butenedioate in Pd-catalyzed addition of bis(ferrocenyl)mercury to dimethylacetylenedicarboxylate has been confirmed by X-ray analysis. (C) 2001 Elsevier Science BN. All rights reserved.