N1,n1-双(4-氟苯基)丙二酰胺 | 1677-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N1,n1-双(4-氟苯基)丙二酰胺
• 英文名称: N¹,N³-bis(4-fluorophenyl)malonamide
• 英文别名: N,N'-bis(4-fluorophenyl)malonamide；N,N'-di-(4-flourophenyl)malonamide；N,N'-di(4-fluorophenyl)malonamide；Malonsaeure-bis-<4-fluor-anilid>；Malonsaeure-bis-(4-fluor-anilid)；N,N'-bis(4-fluorophenyl)propanediamide
• CAS: 1677-29-8
• 化学式: C₁₅H₁₂F₂N₂O₂
• mdl: MFCD00118891
• 分子量: 290.269
• InChiKey: IHPIXCWMIRALHO-UHFFFAOYSA-N

物化性质

• 熔点：
  211 °C
• 沸点：
  549.3±45.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)
• 溶解度：
  3.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  N1,n1-双(4-氟苯基)丙二酰胺 在 盐酸 、 甲烷磺酸 、 四磷十氧化物 作用下， 以 水 为溶剂， 反应 4.0h， 生成 6-fluoro-4-hydroxy-3-((3-nitrophenyl)diazenyl)quinolin-2(1H)-one
  参考文献：
  名称：

  6-氟-4-羟基-2-喹诺酮重氮偶合产物中溶剂变色现象的研究

  摘要：

  由相应的二苯胺的环缩合反应合成了6-氟4-羟基-2-喹诺酮，随后用作与某些重氮化的芳族胺的有效偶联组分。制备的偶氮染料通过紫外可见，FT-IR，1 H NMR光谱技术和元素分析进行表征。关于在六种溶剂：乙酸，甲醇，氯仿，乙腈，二甲基亚砜和二甲基甲酰胺中的最大吸收波长（λmax），评估了染料的溶剂溶变色。关于苯环上取代基的性质讨论了染料的颜色。还报道了酸和碱对染料可见吸收光谱的影响。电离常数pK a，在80体积％的乙醇-水介质在室温下进行了测定，并与取代基常数，σ相关这些染料X。

  DOI：

  10.1016/j.molliq.2011.03.011
• 作为产物：
  描述：

  丙二酸二甲酯 、 4-氟苯胺 反应 4.0h， 以91%的产率得到N1,n1-双(4-氟苯基)丙二酰胺
  参考文献：
  名称：

  6-氟-4-羟基-2-喹诺酮重氮偶合产物中溶剂变色现象的研究

  摘要：

  由相应的二苯胺的环缩合反应合成了6-氟4-羟基-2-喹诺酮，随后用作与某些重氮化的芳族胺的有效偶联组分。制备的偶氮染料通过紫外可见，FT-IR，1 H NMR光谱技术和元素分析进行表征。关于在六种溶剂：乙酸，甲醇，氯仿，乙腈，二甲基亚砜和二甲基甲酰胺中的最大吸收波长（λmax），评估了染料的溶剂溶变色。关于苯环上取代基的性质讨论了染料的颜色。还报道了酸和碱对染料可见吸收光谱的影响。电离常数pK a，在80体积％的乙醇-水介质在室温下进行了测定，并与取代基常数，σ相关这些染料X。

  DOI：

  10.1016/j.molliq.2011.03.011

文献信息

• Manganese(III)-Mediated Oxidative Radical Cyclization 3. Synthesis of 3-Azabicyclo[3.3.0]-octan-2-ones and Related Compounds in the Reaction of 1,1,6,6-Tetraarylhexa-1,5-dienes with N,N’-Disubstituted Malonamides
  作者：Hiroshi Nishino、Kiyotaka Ishida、Hideaki Hashimoto、Kazu Kurosawa

  DOI：10.1055/s-1996-4310

  日期：1996.7

  The oxidation of 1,1,6,6-tetraarylhexa-1,5-dienes with manganese(III) acetate in the presence of N,N’-diarylmalonamides gave 1-(arylcarbamoyl)-8-(diarylmethylene)-3,4,4-triaryl-3-azabicyclo[3.3.0]octan-2-ones and 4,4,9,9-tetraaryl-2,11-bis(arlyimino)-3,10-dioxatricyclo[6.3.0.01,5]undecanes in good to moderate yields together with 11-(arylimino)-3,4,4,9,9-pentaaryl-10-oxa-3-azatricyclo[6.3.0.01,5]undecan-2-ones. A similar reaction in the presence of N,N’-dimethylmalonamide also yielded 3-azabicyclo[3.3.0]octan-2-one derivatives. An acid-catalyzed decomposition of the tricyclic diimines in acetic acid caused ring opening, while a similar decomposition in anhydrous THF resulted in recyclization at the nitrogen atom and/or hydrolysis of one of the imine bonds. A modification for the synthesis of 3-azabicyclo[3.3.0]octan-2-ones is discussed according to the results of the acid-catalyzed decomposition of the tricyclic imines.

  在 N,N'-二芳基丙二酰胺存在下，用乙酸锰 (III) 氧化 1,1,6,6-四芳基六-1,5-二烯，得到 1-(芳基氨基甲酰基)-8-(二芳基亚甲基)-3,4 ,4-三芳基-3-氮杂双环[3.3.0]辛烷-2-酮和4,4,9,9-四芳基-2,11-双(芳基亚氨基)-3,10-二氧三环[6.3.0.01,5]十一烷与 11-(芳基亚氨基)-3,4,4,9,9-五芳基-10-氧杂-3-氮杂三环[6.3.0.01,5]十一烷-2-酮一起产率良好至中等。在 N,N'-二甲基丙二酰胺存在下的类似反应也产生了 3-氮杂双环[3.3.0]辛烷-2-酮衍生物。三环二亚胺在乙酸中的酸催化分解导致开环，而无水THF中的类似分解导致氮原子再环化和/或亚胺键之一水解。根据三环亚胺的酸催化分解结果，讨论了3-氮杂双环[3.3.0]辛烷-2-酮合成的改进。
• Modified malonate derivatives
  申请人：Merck Sharp & Dohme Corp.

  公开号：US08158825B2

  公开（公告）日：2012-04-17

  The present invention relates to a novel class of modified malonate derivatives. The modified malonate compounds can be used to treat cancer. The modified malonate compounds can also inhibit histone deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplastic cells, thereby inhibiting proliferation of such cells. Thus, the compounds of the present invention are useful in treating a patient having a tumor characterized by proliferation of neoplastic cells. The compounds of the invention may also be useful in the prevention and treatment of TRX-mediated diseases, such as autoimmune, allergic and inflammatory diseases, and in the prevention and/or treatment of diseases of the central nervous system (CNS), such as neurodegenerative diseases. The present invention further provides pharmaceutical compositions comprising the modified malonate derivatives and safe dosing regimens of these pharmaceutical compositions, which are easy to follow, and which result in a therapeutically effective amount of the modified malonate derivatives in vivo.

  本发明涉及一类新型的改性丙二酸酯衍生物。这些改性丙二酸酯化合物可用于治疗癌症。这些改性丙二酸酯化合物也可以抑制组蛋白去乙酰化酶，并适用于选择性诱导细胞末端分化、阻止肿瘤细胞生长和/或细胞凋亡，从而抑制这些细胞的增殖。因此，本发明的化合物对于治疗具有肿瘤细胞增殖特征的患者非常有用。本发明的化合物还可用于预防和治疗TRX介导的疾病，例如自身免疫、过敏和炎症性疾病，以及中枢神经系统（CNS）疾病的预防和/或治疗，例如神经退行性疾病。本发明还提供了包含改性丙二酸酯衍生物的药物组合物和这些药物组合物的安全剂量方案，易于遵循，并在体内产生治疗有效量的改性丙二酸酯衍生物。
• Modified Malonate Derivatives
  申请人：Grimm Jonathan

  公开号：US20100160327A1

  公开（公告）日：2010-06-24

  The present invention relates to a novel class of modified malonate derivatives. The modified malonate compounds can be used to treat cancer. The modified malonate compounds can also inhibit histone deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplastic cells, thereby inhibiting proliferation of such cells. Thus, the compounds of the present invention are useful in treating a patient having a tumor characterized by proliferation of neoplastic cells. The compounds of the invention may also be useful in the prevention and treatment of TRX-mediated diseases, such as autoimmune, allergic and inflammatory diseases, and in the prevention and/or treatment of diseases of the central nervous system (CNS), such as neurodegenerative diseases. The present invention further provides pharmaceutical compositions comprising the modified malonate derivatives and safe dosing regimens of these pharmaceutical compositions, which are easy to follow, and which result in a therapeutically effective amount of the modified malonate derivatives in vivo.

  本发明涉及一种新的改性丙二酸酯衍生物类，这些改性丙二酸酯化合物可用于治疗癌症。这些改性丙二酸酯化合物还可以抑制组蛋白去乙酰化酶，并适用于选择性诱导终末分化，阻止肿瘤细胞生长和/或凋亡，从而抑制这些细胞的增殖。因此，本发明的化合物在治疗具有肿瘤细胞增殖特征的患者方面非常有用。本发明的化合物还可以用于预防和治疗TRX介导的疾病，例如自身免疫、过敏和炎症性疾病，并用于预防和/或治疗中枢神经系统（CNS）疾病，例如神经退行性疾病。本发明还提供了包括改性丙二酸酯衍生物的药物组合物和这些药物组合物的安全用药方案，这些方案易于遵循，并在体内产生治疗有效量的改性丙二酸酯衍生物。
• C–C Bond Cleavage Mediated Reaction for Constructing 3-Carbonyl Imidazo[1,5-<i>a</i>] Pyridines from 1,3-Dicarbonyl Compounds and Pyridin-2-ylmethanamines
  作者：Qiang Wang、Xia Yao、Peilan Zhao、Wanxiang Liu、Wangyan Zhao、Xin Fang、Yun Zhu、Gangqiang Dai

  DOI：10.1021/acs.joc.3c01425

  日期：2023.10.6

  cyclization and C–C bond cleavage process mediated reaction for constructing 3-carbonyl imidazo[1,5-a] pyridines from 1,3-dicarbonyl compounds and pyridin-2-ylmethanamines has been developed. Various 1,3-dicarbonyl compounds are applicable, and selectivity could be achieved. Importantly, this strategy could be extended to an atom economy method by employing a cyclic 1,3-dicarbonyl compound, and it provided

  开发了一种[4 + 1]环化和C-C键断裂过程介导的反应，用于从1,3-二羰基化合物和吡啶-2-基甲胺构建3-羰基咪唑并[1,5-a]吡啶。多种1,3-二羰基化合物均可适用，且可实现选择性。重要的是，该策略可以通过使用环状1,3-二羰基化合物扩展到原子经济方法，并为C-C键断裂反应提供了新的视角。
• Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity
  作者：Matías D. Ferretti、Alexandre T. Neto、Ademir F. Morel、Teodoro S. Kaufman、Enrique L. Larghi

  DOI：10.1016/j.ejmech.2014.05.024

  日期：2014.6

  A novel series of symmetrically substituted 3,3-dibenzy1-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4'-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. (C) 2014 Elsevier Masson SAS. All rights reserved.