2-methyl-4-[(E)-(4-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one | 711015-30-4

• 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: 2-methyl-4-[(E)-(4-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one
• 英文别名: 4-(p-nitrobenzylidene)-2-methyl-5-oxazolone；5-oxo-2-methyl-4-(4'-nitrobenzylidene)-4,5-dihydrooxazole；(E)-2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one；2-methyl-4-(4-nitro-benzyliden)-4H-oxazol-5-one；2-Methyl-4-(4-nitro-benzyliden)-4H-oxazol-5-on；2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one；(4E)-2-methyl-4-[(4-nitrophenyl)methylidene]-1,3-oxazol-5-one
• CAS: 711015-30-4
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: ODNSPFZFMYOBLW-UXBLZVDNSA-N

物化性质

• 熔点：
  273 °C(Solv: ethanol (64-17-5); hexane (110-54-3); water (7732-18-5))
• 沸点：
  350.2±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-4-[(E)-(4-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one 在 盐酸 作用下， 生成 2-hydroxy-3-(4-nitrophenyl)acrylic acid
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8
• 作为产物：
  描述：

  (Z)-2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one 以 乙腈 为溶剂， 以17%的产率得到2-methyl-4-[(E)-(4-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one
  参考文献：
  名称：

  Benzylidene-Oxazolones as Molecular Photoswitches

  摘要：

  The synthesis and photochemical study of a family of molecular switches inspired by the green fluorescent protein (UP) chromophore is presented. These compounds can be easily synthesized, and their photophysical properties may be tuned. Due to their efficient photoisomerization and high stability, these compounds can be switched on/off by using light and heat or light with different wavelengths.

  DOI：

  10.1021/ol301741g

文献信息

• Compounds and Their Salts Specific to the PPAR Receptors and the EGF Receptors and Their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20090048343A1

  公开（公告）日：2009-02-19

  The present invention relates to compounds comprising the general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR 3 , —CH(OR 3 )COOH, in which R 3 is selected from H, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及具有一般式（I）的化合物，其中R1和R2，可以相同也可以不同，选自包括-H或具有1至6个碳原子的直链或支链烷基基团，或者共同形成具有5或6个原子的芳香或脂肪环的群；Y和Z，可以相同也可以不同，选自包括-H，-OH，-COOH，-OR3，-CH(OR3)COOH的群，其中R3选自H，苯基，苄基，-CF3或-CF2CF3，乙烯基，烯丙基和具有1至6个碳原子的直链或支链烷基基团。
• Reaction of 4-benzylidene-2-methyl-5-oxazolone with amines, Part 2: Influence of substituents in para-position in the phenyl ring and a substituent on amine nitrogen atom on the reaction kinetics
  作者：B. Bet?akowska、B. Banecki、C. Czaplewski、L. ?ankiewicz、W. Wiczk

  DOI：10.1002/kin.10039

  日期：2002.3

  ring-opening reaction was studied. The substituents (OH, OCH3, N(CH3)2, Cl, NO2) in para-position of the phenyl ring of Ox substantially modified the rate of the reaction with benzylamine in acetonitrile. The rate of the Ox ring-opening reaction decreased with increase of the electron-donating properties of the substituent. A good correlation between the rate constants of the reaction of 4-(4′-sub

  胺（苄胺、N-甲基-苄胺、N-异丙基-苄胺、N-甲基-丁胺、N-乙基-丁胺、仲丁胺和叔丁胺）的结构对速率常数的影响研究了4-亚苄基-2-甲基-5-恶唑酮(Ox)的开环反应。速率常数的对数与查顿的空间取代基常数 ν 之间的良好相关性以及与简单支化方程形式的良好相关性表明，由于亲核试剂的 C1 碳原子上的取代降低了反应速率，因此存在空间效应。另外，研究了Ox的亚苄基部分的结构对恶唑酮开环反应速率的影响。取代基（OH、OCH3、N(CH3)2、Cl、NO2) 在 Ox 的苯环的对位上显着改变了与苄胺在乙腈中的反应速率。Ox开环反应的速率随着取代基给电子性质的增加而降低。4-(4'-取代的亚苄基)-2-甲基-5-恶唑酮与苄胺反应的速率常数与反应中心的电子密度（恶唑酮环的 C5 碳）之间具有良好的相关性，计算公式为建立了从头算法，建立了Hammett取代基常数和CR方程。© 2002 Wiley Periodicals
• Synthesis of novel bifunctional chelators and their use in preparing monoclonal antibody conjugates for tumor targeting
  作者：David A. Westerberg、Patrick L. Carney、Patrick E. Rogers、Steven J. Kline、David K. Johnson

  DOI：10.1021/jm00121a042

  日期：1989.1

  carboxymethylation, reduction of the nitro group, and reaction with thiophosgene. The resulting isothiocyanate derivatives reacted with monoclonal antibody B72.3 to give antibody-chelator conjugates containing 3 mol of chelator per mole of immunoglobulin, without significant loss of immunological activity. Such conjugates, labeled with the radioisotopic metal indium-111, selectively bound a human colorectal

  螯合剂乙二胺四乙酸和二亚乙基三胺五乙酸的双官能衍生物，其中对-异硫氰酸根合苄基部分连接在一个羧甲基臂的亚甲基碳原子上，是通过用（对硝基苯基）丙酮酸将相关的多胺还原烷基化，然后进行羧甲基化，还原硝基，并与硫光气反应。所得异硫氰酸酯衍生物与单克隆抗体B72.3反应，得到抗体-螯合剂结合物，每摩尔免疫球蛋白含3摩尔螯合剂，而免疫活性没有明显损失。当用静脉注射时，这种标记有放射性同位素金属铟111的结合物可以选择性结合植入裸鼠体内的人类结直肠癌。正常组织中的摄取与已知双功能螯合剂的类似共轭物相比可比或更低。结论是，在聚氨基多羧酸螯合剂中该位置上的蛋白质反应性基团的取代不会充分改变这些分子的螯合性质，从而不会不利地影响生物分布，因此提供了合成这种螯合剂的一般方法。
• Compounds and their Salts Specific to the PPAR Receptors and the EGF Receptors and their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20130005813A1

  公开（公告）日：2013-01-03

  The present invention relates to compounds comprising the general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR 3 , —CH(OR 3 )COOH, in which R 3 is selected from H, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及通式（I）的化合物，其中R1和R2可以相同或不同，选自包括-H或具有1到6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环的群体；Y和Z可以相同或不同，选自包括-H、-OH、-COOH、-OR3、-CH（OR3）COOH的群体，其中R3选自H、苯基、苄基、-CF3或-CF2CF3、乙烯基、丙烯基和具有1到6个碳原子的线性或支链烷基。
• Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field
  申请人：Nogra Pharma Limited

  公开号：US10016381B2

  公开（公告）日：2018-07-10

  The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR3, —CH(OR3)COOH, in which R3 is selected from H, phenyl, benzyl, —CF3 or —CF2CF3, vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及包含通式(I)的化合物，其中 R1 和 R2（可以相同或不同）选自-H 或具有 1 至 6 个碳原子的直链或支链烷基，或共同形成具有 5 或 6 个原子的芳香族或脂肪族环；Y 和 Z（可以相同或不同）选自-H、-OH、-COOH、-OR3、-CH(OR3)COOH 组，其中 R3 选自 H、苯基、苄基、-CF3 或-CF2CF3、乙烯基、烯丙基和具有 1 至 6 个碳原子的直链或支链烷基。