methyl 4-fluoro-3-nitrocinnamate | 209607-59-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 4-fluoro-3-nitrocinnamate
• 英文别名: (E)-methyl 3-(4-fluoro-3-nitrophenyl)acrylate；methyl (E)-3-(4-fluoro-3-nitrophenyl)acrylate；3-(4-Fluoro-3-nitro-phenyl)-acrylic acid methyl ester；methyl (E)-3-(4-fluoro-3-nitrophenyl)prop-2-enoate
• CAS: 209607-59-0
• 化学式: C₁₀H₈FNO₄
• 分子量: 225.176
• InChiKey: YQWIWXOIMLZUJQ-HWKANZROSA-N

物化性质

• 沸点：
  341.6±32.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-fluoro-3-nitrocinnamate 在 Wilkinson's catalyst 、 氢气 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、303.97 kPa 条件下， 反应 8.0h， 以95%的产率得到methyl 3-(4-fluoro-3-nitrophenyl)propanoate
  参考文献：
  名称：

  Simplified Cyclic Analogues of Bastadin-5. Structure−Activity Relationships for Modulation of the RyR1/FKBP12 Ca²⁺ Channel Complex

  摘要：

  Bastadin-5, a brominated macro-dilactam from the marine sponge Ianthella basta, enhances release of Ca2+ from stores within the sarcoplasmic reticulum (SR) of muscle and nonmuscle cells by modulating RyR1/FKBP12 complex. Analogues of bastadin-5 present desirable targets for SAR studies to shed light on the gating mechanism and locus of bastadin-5 binding on these heteromeric channels that mediate essential steps in early coupling of membrane excitation to Ca2+ signaling cascades. Simple, ring-constrained analogues of bastadin-5 were synthesized from substituted benzaldehydes in a convergent manner, featuring an efficient SNAr macroetherification, and evaluated in an assay that measures [H-3]-ryanodine that is known to correlate with the functional open state of the Ca2+ channel. The simplified 14-membered ring, atropisomeric analogue (+/-)-7, like bastadin-5, enhanced ryanodine binding to the RyR1/FKBP12 complex (EC50 11 mu M), however, unexpectedly, the corresponding achiral 18-membered ring analogue 14 potently inhibited binding (IC50 6 mu M) under the same conditions. Structure-activity relationships of both families of cyclic analogues showed activity in a ryanodine binding assay that varied with substitutions of the Br atom on the trisubstituted aryl ring by various functional groups. The most active analogues were those that conserved the dibromocatechol ether moiety that corresponds to the 'western edge' of the bastadin-5 structure. These data suggest that cyclic analogues of bastadin-5 interact with the channel complex in a complex manner that can either enhance or inhibit channel activity.

  DOI：

  10.1021/jm050708u
• 作为产物：
  描述：

  4-氟-3-硝基苯胺 、 丙烯酸甲酯（MA） 在 tetrafluoroboric acid 、 sodium nitrite 、 palladium diacetate 、 calcium carbonate 作用下， 以 水 、 甲醇 为溶剂， 反应 0.5h， 以34%的产率得到methyl 4-fluoro-3-nitrocinnamate
  参考文献：
  名称：

  Simple NIR complexes and their applicability in dye-sensitized solar cells

  摘要：

  Novel nickel(II)benzo-dfirnino-semiquinonate and palladium(II)benzo-imino-semiquinonate complexes were synthesized, tested regarding their applicability in dye sensitized solar cells, and characterized optically and electrochemically. All the dyes showed a strong absorption in the near infrared region. Various electron-withdrawing substituents were introduced into the complex ligands and evaluated with respect to the effect on the energy level of the frontier molecular orbitals. Energetically suitable complexes were then tested in TiO2 based dye-sensitized solar cells with different iodide-based electrolytes. Two of them exhibited energy conversion abilities suggesting their candidacy as co-sensitizers to known visible light-absorbing dyes in order to extend the spectral window used for light harvesting into the infrared region to increase the total conversion efficiency of the cell. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.07.015

文献信息

• EP2 RECEPTOR AGONISTS
  申请人：Oxford Alexander William

  公开号：US20100130556A1

  公开（公告）日：2010-05-27

  A compound of formula (III): or a salt, solvate and chemically protected form thereof, wherein: R 5 is an optionally substituted C 5-20 aryl or C 4-20 alkyl group; L′ is a single bond, —O— or —C(═O)—; A is selected from the group consisting of: formulae (i) (ii) (iii) wherein X and Y are selected from the group consisting of: O and CR 3 ; S and CR 3 ; NH and CR 3 ; NH and N; O and N; S and N; N and S; and N and O, and where the dotted lines indicate a double bond in the appropriate location, and where Q is either N or CH; D is selected from: formulae (i) (ii) (iii) (iv) (v) (vii) (viii) (ix) B is selected from the group consisting of: formulae (A) (B) where R P6 is selected from fluoro and chloro; and R 2 is either: (i) —CO 2 H; (ii) —CONH 2 ; (iii) —CH 2 —OH; or (iv) tetrazol-5-yl.

  公式（III）的化合物：或其盐、溶剂合物和化学保护形式，其中：R5是可选择取代的C5-20芳基或C4-20烷基基团；L′是单键，—O—或—C(═O)—；A选自以下组：式（i）（ii）（iii），其中X和Y选自以下组：O和CR3；S和CR3；NH和CR3；NH和N；O和N；S和N；N和S；和N和O，其中虚线表示适当位置的双键，Q是N或CH；D从以下中选择：式（i）（ii）（iii）（iv）（v）（vii）（viii）（ix）B从以下组中选择：式（A）（B），其中RP6选自氟和氯；R2是：（i）—CO2H；（ii）—CONH2；（iii）—CH2—OH；或（iv）四唑-5-基。
• BENZIMIDAZOLE DERIVATIVES AND USE THEREOF AS IDH1 INHIBITORS
  申请人：KPC Pharmaceuticals, Inc.

  公开号：EP3816158A1

  公开（公告）日：2021-05-05

  The present invention relates to benzimidazole compounds and an application thereof as IDH1 mutant inhibitors, in particular, to a compound as represented by formula (I), tautomers thereof, or pharmaceutically acceptable salts thereof.

  本发明涉及苯并咪唑化合物及其作为IDH1突变体抑制剂的应用，特别是涉及由式（I）代表的化合物、其同系物或其药学上可接受的盐。
• Benzimidazole derivatives and use thereof as IDH1 inhibitors
  申请人：KPC PHARMACEUTICALS, INC.

  公开号：US11407717B2

  公开（公告）日：2022-08-09

  The present invention relates to benzimidazole compounds and an application thereof as IDH1 mutant inhibitors, in particular, to a compound as represented by formula (I), tautomers thereof, or pharmaceutically acceptable salts thereof.

  本发明涉及苯并咪唑化合物及其作为IDH1突变体抑制剂的应用，特别是涉及由式（I）代表的化合物、其同系物或其药学上可接受的盐。
• [EN] CATALYTIC ASYMMETRIC AMIDOHYDROXYLATION OF OLEFINS WITH N-HALO CARBOXAMIDES<br/>[FR] AMIDOHYDROXYLATION ASYMETRIQUE CATALYTIQUE D'OLEFINES AU MOYEN DE N-HALO CARBOXAMIDES
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1998027051A2

  公开（公告）日：1998-06-25

  (EN) $g(b)-Hydroxyamides are synthesized from olefin substrates by means of a catalyzed asymmetric addition reaction. N-halo carboxamides are employed as the oxidant nitrogen source for the production of the $g(b)-hydroxysulfonamides. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantio-selectively. Divalent ligands are preferred over monovalent ligands because of their enhanced regio- and enantio-selectivity. Excellent yields and enantiomeric efficiencies are achieved with both organic solvents (homogeneous conditions) and co-solvent conditions (heterogenous conditions), generally containing a 50/50 (v/v) mixtures of water and organic solvent.(FR) L'invention concerne des $g(b)-hydroxyamides synthétisés à partir de substrats d'oléfine au moyen d'une réaction d'addition asymétrique catalytique. Des N-halo carboxamides sont employés en tant que source d'azote oxydante pour la production de $g(b)-hydroxysulfonamides. La réaction d'addition est catalysée par de l'osmium et est co-catalysée par des ligands chiraux. Les ligands chiraux, outre qu'ils constituent des co-catalyseurs avec l'osmium, servent également à diriger la réaction d'addition de façon régionalement et énantiomèrement sélective. Des ligands divalents sont préférés à des ligands monovalents en raison de leur sélectivité accrue pour une région et pour un énantiomère. On obtient d'excellents rendements et des énantiomères très efficaces à la fois avec des solvants organiques (conditions homogènes) et des co-solvants (conditions hétérogènes) contenant généralement des mélanges 50/50 (en volume) d'eau et de solvant organique.

  $g(b)$-羟基胺类化合物通过催化的不对称加成反应由烯ylene基底物合成。N-卤代二碳酸胺类化合物被用作生产$g(b)$-羟基硫化酰胺类化合物所需的氧化态氮源。加成反应由锇催化，并由协同催化的环状配位体介导。配位体除了协同催化的锇之外，还起到控制加成反应的位置选择和构型选择的作用。二价配位体相较于一价配位体更受青睐，因为它们能显著提高位置选择和构型选择的效率。无论是溶剂条件（均匀条件）还是共溶剂条件（非均匀条件），当水和有机溶剂按50/50体积比混合时，都可以得到优异的产率和反析度。其中，已有12例的逆式加成环境下，所得产物均为单一的结构，其反析度超过99%。这些产物都是由具有不同数目化学键的二价配位体所合成的，且这些配位体都是非键合的。但由于有时候需要将加成条件与随后的反应条件结合起来，所以这些产物并无法直接用来用于接下来的反应。 (FR) $b(g)$-hydroxamides are synthesized from olefin substrates by means of a catalyzed asymmetric addition reaction. N-halo carboxamides are employed as the oxidant nitrogen source for the production of the $b(g)$-hydroxysulfonamides. The addition reaction is catalyzed by an osmium and is co-catalyzed by chiral ligands. The chiral ligands, besides being co-catalysts to osmium, also serve to direct the addition reaction regioselectively and enantioselectively. Divalent ligands are preferred over monovalent ligands because of their enhanced regio- and enantio-selectivity. Excellent yields and enantiomeric efficiencies are achieved with both organic solvents (homogeneous conditions) and co-solvent conditions (heterogeneous conditions), generally containing a 50/50 (v/v) mixture of water and organic solvent.
• Application of a new combination of palladium and CaCO3 for an aerobic Heck reaction using arenediazonium-salts
  作者：Heiko Brunner、Nathalie Le Cousturier de Courcy、Jean-Pierre Genêt

  DOI：10.1016/s0040-4039(99)00921-1

  日期：1999.6

  Efficient Heck reactions under aerobic conditions were carried out using Pd-catalyst in the presence of CaCO3. Under these conditions a neat Heck Reaction using arenediazonium salts bearing functional groups including nitro functionalities can generally take place in good yields up to 95%. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.