methyl benzoate | 222714-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl benzoate
• 英文别名: (S)-N-(2-chloroethanoyl)-2-(p-carboxymethylphenyl)ethylamine；methyl [N-2-(chloroethanoyl)-4-(S)-(1-aminoethyl)]benzoate；methyl 4{(1S)-1-[(2-chloroacetyl)amino]ethyl}benzoate；4-[(S)-1-(2-chloro-acetylamino)-ethyl]-benzoic acid methyl ester；methyl 4-[(1S)-1-[(2-chloroacetyl)amino]ethyl]benzoate
• CAS: 222714-40-1
• 化学式: C₁₂H₁₄ClNO₃
• 分子量: 255.701
• InChiKey: AOEZYMWTHUKLER-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S)-1-(7-tert-butyl-2-(pyrazoylmethyl)-1-azaxanthone)-4,10-(1-(1-phenyl)ethyl-carbamoylmethyl)-1,4,7,10-tetrazacyclododecane 、 methyl benzoate 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以79%的产率得到methyl 4-[(S)-1-(2-{7-[1-(6-tert-butyl-10-oxo-10H-9-oxa-1-aza-anthracen-2-yl)-1H-pyrazol-3-ylmethyl]-4,10-bis[((S)-1-phenyl-ethylcarbamoyl)methyl]-1,4,7,10-tetraaza-cyclododec-1-yl}-acetylamino)-ethyl]-benzoate
  参考文献：
  名称：

  Effective and efficient sensitisation of terbium luminescence at 355 nm with cell permeable pyrazoyl-1-azaxanthone macrocyclic complexes

  摘要：

  发射性铽配合物，适用于蛋白质共价结合，其包含吡唑啉基-1-氮杂咕吨染料发色团，已成功制备；它们展现细胞摄取能力，并具有较低的激发态淬灭敏感性。

  DOI：

  10.1039/b709805g
• 作为产物：
  描述：

  (S)-4-(1-氨基乙基)苯甲酸盐酸盐 在 盐酸 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 methyl benzoate
  参考文献：
  名称：

  Synthesis, Time-Resolved Luminescence, NMR Spectroscopy, Circular Dichroism and Circularly Polarised Luminescence Studies of Enantiopure Macrocyclic Lanthanide Tetraamide Complexes

  摘要：

  The syntheses and properties of a series of lanthanide complexes (Ln = Eu, Tb, Dy, Yb) of C-4 symmetric chiral tetraamide ligands based on 1,4,7,10-tetraazacyclododecane are reported. The configuration of the chiral centre at carbon in the amide substituent (CH2NHCO-CH(Me)Ar) determines the helicity of the derived complex and the configuration of the macrocyclic ring. The enantiopure lanthanide complexes do not undergo Delta/Lambda interconversion in the temperature range 220 to 320 K and three complexes have been characterised by X-ray crystallography, revealing nine-coordination about the lanthanide ion (Ln=Eu, Dy) with a monocapped square-antiprismatic coordination geometry. The terbium complexes are highly emissive in aqueous solution following excitation into the aryl chromophore (e.g. for [Tb .(R)-7a](3+) phi H2O = 0.49; phi D2O = 0.81) and all of the lanthanide complexes exhibit strong circularly polarised luminescence. The ytterbium complexes (e.g. [Yb .(S)-5b](3+)) shows a strong near-IR CD and circularly polarised luminescence (CPL) associated with the F-2(5/2)-F-2(7/2) transition. Overall, these emissive complexes allow control in modulating both the frequency and the polarisation of emitted light in aqueous solution.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<1095::aid-chem1095>3.0.co;2-c

文献信息

• Emissive and Cell-Permeable 3-Pyridyl- and 3-Pyrazolyl-4-azaxanthone Lanthanide Complexes and Their Behaviour<i>in cellulo</i>
  作者：Craig P. Montgomery、Elizabeth J. New、Lars O. Palsson、David Parker、Andrei S. Batsanov、Laurent Lamarque

  DOI：10.1002/hlca.200900122

  日期：2009.11

  seven emissive europium(III) and terbium(III) complexes was prepared, incorporating a 3‐pyridyl‐4‐azaxanthone or 3‐pyrazolyl‐4‐azaxanthone sensitising moiety within a polydentate macrocyclic ligand. High overall emission quantum yields in aqueous media are attenuated in the presence of protein or certain oxy anions due to displacement of the N,N′‐chelated sensitiser. Nevertheless, these complexes are

  制备了一系列七个发射性euro（III）和b（III）配合物，在多齿大环配体中结合了3-吡啶基-4-氮杂蒽酮或3-吡唑基-4-氮杂蒽酮敏化部分。由于N，N'螯合的敏化剂的置换，在蛋白质或某些氧阴离子存在下，水性介质中较高的总发射量子产率会降低。然而，这些复合物被带入细胞并倾向于在线粒体的最初几个小时内定位，然后被运至内体区室。在存在竞争性抑制剂或定义明确的摄取途径的启动子的情况下，细胞摄取研究揭示了涉及巨胞饮作用的常见摄取机制。
• [EN] PYRIDYL-AZA(THIO)XANTHONE SENSITIZER COMPRISING LANTHANIDE(III) ION COMPLEXING COMPOUNDS, THEIR LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS.<br/>[FR] SENSIBILISATEUR PYRIDYL-AZA(THIO)XANTHONE COMPRENANT DES COMPOSÉS COMPLEXANT LES IONS LANTHANIDE(III), LEURS COMPLEXES DES IONS LANTHANIDE(III) LUMINESCENTS ET LEUR UTILISATION COMME MARQUEURS FLUORESCENTS
  申请人：CIS BIO INT

  公开号：WO2010084090A1

  公开（公告）日：2010-07-29

  Lanthanide (III) Ion completing compound comprising: (1) a sensitizer moiety of Formula (I) in which: a is an integer from 1 to 4; b is an integer equal to 1 or 2; c is an integer equal to 1 or 2; (R1)a, (R2)b, (R3)C are the same or different and are chosen from the group consisting of H; alkyl; -COOR4 where R4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF3; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R3, two consecutive R2 or two consecutive R1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X1 and X2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from -CH2- or -(CH2)2-, said moiety being covalentiy attached to (2) a lanthanide (in) ion chelating moiety through A. The above compounds are used in the preparation of luminescent lanthanide (III) ion complexes which are used as fluorescent labels.

  镧系（III）离子配合物包括：（1）式（I）中的感光团，其中：a是1到4之间的整数；b是等于1或2的整数；c是等于1或2的整数；（R1）^a，（R2）^b，（R3）^c相同或不同，并选自H；烷基；-COOR4，其中R4为H或烷基；芳基；杂芳基；饱和或不饱和环烃；CF3；CN；卤原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1组成芳基或杂芳基或饱和或不饱和环烃基；其中L是连接物，Rg是反应性基团，Sc是共轭物质；X1和X2相同或不同，为O或S；A是直接键或从-CH2-或-( )2-中选择的二价基团，所述团通过A与（2）中的镧系（III）离子螯合团结合。上述化合物用于制备发光的镧系（III）离子配合物，用作荧光标记剂。
• [EN] LANTHANIDE (III) ION COMPLEXING COMPOUNDS, LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS<br/>[FR] COMPOSÉS COMPLEXANT LES IONS LANTHANIDE (III), COMPLEXES LUMINESCENTS D'IONS LANTHANIDE (III) ET LEUR UTILISATION COMME MARQUEURS FLUORESCENTS
  申请人：CIS BIO INT

  公开号：WO2009010580A1

  公开（公告）日：2009-01-22

  Lanthanide (III) ion complexing compound comprising: (1) a sensitizer moiety of formula (I) in which: a is an integer from 1 to 4; b is an integer equal 1 or 2; c is an integer equal to 1 or 2; (R1)a, (R2)b, (R3)C are the same or different and are chosen from the group consisting of: H; alkyl; -COOR4 where R4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF3; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R3, two consecutive R2 or two consecutive R1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X1 and X2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from -CH2- or -(CH2)2-, said moiety being covalently attached to (2) a lanthanide (III) ion chelating moiety through A. Application: Preparation of luminescent lanthanide (III) ion complexes and use thereof as fluorescent labels.

  镧系（III）离子络合物，包括：（1）具有以下式（I）的感光基团，其中：a是1到4之间的整数；b是等于1或2的整数；c是等于1或2的整数；（R1）^a，（R2）^b，（R3）^c相同或不同，并选自以下群体：H；烷基；-COOR4，其中R4为H或烷基；芳基；杂环芳基；饱和或不饱和环烃；CF3；CN；卤原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1基团共同形成芳基或杂环芳基或饱和或不饱和环烃基团；其中L是连接物，Rg是反应性基团，Sc是共轭物质；X1和X2相同或不同，为O或S；A是直接键或从-CH2-或-( )2-中选择的二价基团，所述基团通过A与（2）具有配位基团的镧系（III）离子共价连接。应用：制备发光的镧系（III）离子络合物并将其用作荧光标记剂。
• The Selectivity of Reversible Oxy-Anion Binding in Aqueous Solution at a Chiral Europium and Terbium Center:  Signaling of Carbonate Chelation by Changes in the Form and Circular Polarization of Luminescence Emission
  作者：James I. Bruce、Rachel S. Dickins、Linda J. Govenlock、Thorfinnur Gunnlaugsson、Stefan Lopinski、Mark P. Lowe、David Parker、Robert D. Peacock、Justin J. B. Perry、Silvio Aime、Mauro Botta

  DOI：10.1021/ja001797x

  日期：2000.10.1

  Reversible anion binding in aqueous media at chiral Eu-III and Tbm centers has been characterized by H-1 NMR and by changes in the emission intensity and circular polarization following direct or sensitized (365 nm) excitation via an alkylphenanthridinium chromophore. Using a series of heptadentate tri-amide or polycarboxylate ligands, the affinity for CO32-/HCO3-, phosphate, lactate, citrate, acetate, and malonate at pH 7.4 was found Co decrease as a function of the overall negative charge on the complex: citrate and malonate bound most strongly, and lactate and hydrogen carbonate also formed chelated ternary complexes in, which displacement of both of the metal-bound water molecules occurred, which was confirmed by VT 17-O NMR measurements of-the corresponding Gd complexes. The binding of carbonate was studied in particular, and H-1 NMR and CPL data were obtained that were consistent with the formation of a complex with a reduced helical twist about the metal center. Monohydrogen phosphate was bound in a monodentate manner, giving a mono; aqua adduct. The binding of carbonate to cationic Eu complexes in the presence of a simulated extra-cellular anionic background at pH 7.4 was monitored by variation in the emission intensity, ratio of intensities (615/594 nm), and dissymmetry factors as a function of added total carbonate.