(3,4-二氨基苯)(4-氟苯)甲酮 | 66938-86-1

• 物质功能分类: 有机原料 - 酮类化合物
• 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: (3,4-二氨基苯)(4-氟苯)甲酮
• 中文别名: (3,4-二氨基苯基)(4-氟苯基)甲酮
• 英文名称: (3,4-diaminophenyl)(4-fluorophenyl)ketone
• 英文别名: (3,4-diaminophenyl)(4-fluorophenyl)methanone；3,4-Diamino-4'-fluorobenzophenone；(3,4-diaminophenyl)-(4-fluorophenyl)methanone
• CAS: 66938-86-1
• 化学式: C₁₃H₁₁FN₂O
• mdl: MFCD08063378
• 分子量: 230.242
• InChiKey: KHMJNCNXARCUGR-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114℃ (methanol )
• 沸点：
  447.4±45.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  | 2-8℃ |

反应信息

• 作为反应物：
  描述：

  (3,4-二氨基苯)(4-氟苯)甲酮 在 吡啶 、 sodium hydroxide 、 dicobalt octacarbonyl 、 mercuric acid 、 magnesium 、 ferric nitrate 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 甲苯 、 乙腈 为溶剂， 反应 6.5h， 生成 6-[(E)-1-(4-methylsulfanylphenyl)but-1-en-3-ynyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine
  参考文献：
  名称：

  Synthesis, Antiviral Activity, and Biological Properties of Vinylacetylene Analogs of Enviroxime

  摘要：

  A series of vinylacetylene analogs of Enviroxime (1) was synthesized. The new compounds are potent inhibitors of poliovirus in tissue culture. Cross-sensitivity with Enviroxime-derived mutants shows that the new compounds have the same mechanism of action as Enviroxime, which involves the viral 3A protein. In studies with Rhesus monkeys, the p-fluoro derivative 12 was found to be unique in providing oral bioavailability. Metabolism studies using hepatic microsomes suggest that this procedure would be a useful in vitro method for selecting the appropriate animal model for testing oral absorption. Compound 12 was found to be efficacious by oral administration in treating a Coxsackie A21 infection in CD-1 mice.

  DOI：

  10.1021/jm960718i
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 铂 盐酸 、 氨 、 氢气 作用下， 生成 (3,4-二氨基苯)(4-氟苯)甲酮
  参考文献：
  名称：

  Raeymackers; Van Gelder; Roevens, Arzneimittel-Forschung/Drug Research, 1978, vol. 28, # 4, p. 586 - 594

  摘要：

  DOI：

文献信息

• 氟苯咪唑的合成方法
  申请人：江苏宝众宝达药业股份有限公司

  公开号：CN112094237B

  公开（公告）日：2023-01-20

  本发明涉及一种氟苯咪唑的合成方法，所述合成方法包括如下步骤：1）将还原物和甲酯反应物加入反应瓶中，再加入甲酸，升温至80℃，保温2.5‑3小时；所述还原物、甲酯、甲酸的摩尔比为1:1.2：16‑20；其反应方程式如下：；2）将反应瓶中的溶液注入至甲醇中，并冷却至室温，过滤，即得到所述氟苯咪唑。省去醋酸缩合这一步骤，直接加入过量的甲酸，一步合成氟苯咪唑，反应步骤简单，操作率高，且收率高，约为86.9‑87.6%。
• 一种催化加氢制备高纯度(3,4-二氨基苯基) (4-氟苯基)酮的方法
  申请人：常州齐晖药业有限公司

  公开号：CN104086452B

  公开（公告）日：2016-04-06

  本发明涉及一种催化加氢制备高纯度(3,4-二氨基苯基)(4-氟苯基)酮的方法，属于医药与化工技术领域。该方法是将(4-氨基-3-硝基苯基)(4-氟苯基)酮(I)和催化剂加入有机溶剂中，通入氢气，加氢还原反应，得氟苯咪唑中间体(3,4-二氨基苯基)(4-氟苯基)酮(II)。本发明优点：与用硫氢化钠还原法相比，具有工艺简单、溶剂用量少，反应时间短，且避免了大量含硫化物废水难处理的问题，有利于工业化生产；同时，新型催化剂制备方法简单，具有反应活性高、选择性好和催化剂多次重复使用等特点；新型催化剂与纯Pt/C催化剂相比，可以有效抑制催化加氢过程中羰基被还原成亚甲基和脱氟现象的产生，产品收率和纯度均较高。
• Anti-viral benzimidazole derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0747363A1

  公开（公告）日：1996-12-11

  Certain vinyl acetylene benzimidazole compounds of the formula I which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus.

  某些式 I 的乙烯基乙炔苯并咪唑化合物 可抑制鼻病毒、肠病毒、心病毒、脊髓灰质炎病毒、A 和 B 组柯萨奇病毒、回声病毒和门戈病毒等皮卡病毒的生长。
• Antirhino/Enteroviral Vinylacetylene Benzimidazoles:  A Study of Their Activity and Oral Plasma Levels in Mice
  作者：Mark J. Tebbe、Wayne A. Spitzer、Frantz Victor、Shawn C. Miller、Chris C. Lee、Thomas R. Sattelberg、Emma McKinney、Joseph C. Tang

  DOI：10.1021/jm970423k

  日期：1997.11.1

  In an effort to find an orally bioavailable antiviral for the treatment of rhino/enteroviral infections, a series of vinylacetylene benzimidazoles (11a-o, 12, and 18a was made. Initial studies of this class of antivirals showed that fluorine substitution on the left-hand phenyl ring in combination with the vinylacetylene moiety gave the requisite mix of physical properties to achieve good in vitro antiviral activity as well as respectable oral bioavailability in rhesus monkeys. To ascertain the generality of this finding and to broaden the scope of the structure-activity relationship (SAR), the present study concentrated on fluoro substitution of this class of molecules. The initial antiviral activity for each analogue was measured using human rhinovirus 14 (HRV-14). This served as an indicator of general antiviral activity for SAR purposes. Subsequently, the spectrum of antirhino/enteroviral activity of the more interesting analogues was evaluated through testing against a panel of seven additional rhino/enteroviruses. Broad-spectrum activity was present and consistent for all analogues tested, and it tracked closely with the antiviral activity observed against HRV-14. A simple screening protocol for oral bioavailability was established whereby compounds were administered orally to mice and plasma levels were measured. This procedure facilitated the evaluation of numerous analogues in a rapid manner. The C-max was used as a measure of oral bioavailability to allow relative ranking of compounds. In general, fluorine substitution directly on the left-hand aromatic ring does give good oral blood levels. However, fluorine incorporation at other positions in the molecule was not as effective at maintaining either the activity or the oral plasma levels. The constructive combination of activity and oral plasma levels was maximized in three derivatives: 11a,e,g.
• Ultrasound enhanced synthesis of 1,5-benzodiazepinic heterocyclic rings
  作者：Karla P. Guzen、Rodrigo Cella、Hélio A. Stefani

  DOI：10.1016/j.tetlet.2006.09.043

  日期：2006.11

  1,5-Benzodiazepines are synthesized by a reaction of o-phenylenediamines with a diketone or ketones series by ultrasound irradiation in presence of APTS. The condensation occurred in a mild condition with good to excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.