1-(2-羟基苯基)-2-(2-硝基苯基)乙酮 | 735269-41-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2-羟基苯基)-2-(2-硝基苯基)乙酮
• 英文名称: 1-(2-hydroxyphenyl)-2-(2-nitrophenyl)ethanone
• CAS: 735269-41-7
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: FUHYYDZMCIQBOL-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C(Solv: ethyl acetate (141-78-6); toluene (108-88-3))
• 沸点：
  417.9±25.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-羟基苯基)-2-(2-硝基苯基)乙酮 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以72%的产率得到2-(1H-indol-2-yl)phenol
  参考文献：
  名称：

  α-Arylation of Aryl Ketones: Expanding the Scope of the Truce-Smiles Rearrangement

  摘要：

  Truce-Smiles 重排被应用于合成取代的δ-芳基芳基酮，并通过将其中一种产品转化为取代的吲哚 2-(1H-吲哚-2-基)苯酚证明了该产品的合成用途。

  DOI：

  10.1055/s-0028-1083523
• 作为产物：
  描述：

  (2-nitrophenyl)acetic acid phenyl ester 在 aluminum (III) chloride 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 以45%的产率得到1-(2-羟基苯基)-2-(2-硝基苯基)乙酮
  参考文献：
  名称：

  Ac 2 O介导的2-芳基乙酰基-1-萘的脱芳基乙酰化二聚反应：萘并[1,2-b]呋喃-3-酮的合成。

  摘要：

  通过回流的THF中NaH / Ac2O介导的2-芳基乙酰基-1-萘的脱芳基乙酰化二聚作用，描述了一种合成2-芳基-2-萘基萘并[1,2-b]呋喃-3-酮的新颖有效途径。在开瓶条件下。还提出并讨论了一种可行的机制。一锅转化研究了各种反应条件。

  DOI：

  10.1021/acs.joc.9b03298

文献信息

• [EN] INDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLE
  申请人：UNIV CENTRAL LANCASHIRE

  公开号：WO2014049364A1

  公开（公告）日：2014-04-03

  The present invention relates to compounds for use as therapeutic agents, particularly in the treatment and/or prevention of proliferative disorders, such as cancer, especially brain cancers/tumours, wherein the compounds are generally defined by the formula I: wherein A is an aryl or heteroaryl ring system; and R1 to R 4 are various possible substituent groups, provided that at least one of an R2 group, the R3 group, or an R4 group is or comprises a hydroxy, amino, NH(R x ), or mercapto group.

  本发明涉及化合物作为治疗剂的用途，特别是在治疗和/或预防增生性疾病，如癌症，特别是脑癌/肿瘤方面的应用，其中该化合物通常由公式I定义：其中A是芳基或杂环芳基环系统；R1至R4是各种可能的取代基，但至少一个R2基团、R3基团或R4基团是或包含一个羟基、氨基、NH(Rx)或巯基。
• INDOLE DERIVATIVES
  申请人：UNIVERSITY OF CENTRAL LANCASHIRE

  公开号：US20150272928A1

  公开（公告）日：2015-10-01

  The present invention relates to compounds for use as therapeutic agents, particularly in the treatment and/or prevention of proliferative disorders, such as cancer, especially brain cancers/tumours, wherein the compounds are generally defined by the formula I: wherein A is an aryl or heteroaryl ring system; and R 1 to R 4 are various possible substituent groups, provided that at least one of an R 2 group, the R 3 group, or an R 4 group is or comprises a hydroxy, amino, NH(R x ), or mercapto group.

  本发明涉及用作治疗剂的化合物，特别是用于治疗和/或预防增殖性疾病，如癌症，尤其是脑癌/肿瘤，其中这些化合物通常由式I定义：其中A是芳基或杂环芳基环系；R1至R4是各种可能的取代基，只要其中至少一个R2基团、R3基团或R4基团是或包含一个羟基、氨基、NH(Rx)或巯基。
• A homologous enolate Truce–Smiles rearrangement
  作者：Lorna H. Mitchell、Nicole C. Barvian

  DOI：10.1016/j.tetlet.2004.05.111

  日期：2004.7

  During preparation of a series of diphenyl ethers it was observed that displacement of an activated aryl fluoride with ortho-hydroxyacetophenone afforded a product that was C-arylated adjacent to the ketone. Evidence suggested this product was formed by Smiles rearrangement of an O-arylated intermediate. (C) 2004 Elsevier Ltd. All rights reserved.
• Preliminary biological evaluation and mechanism of action studies of selected 2-arylindoles against glioblastoma
  作者：Saurabh Prabhu、Zaheer Akbar、Frederick Harris、Katherine Karakoula、Robert Lea、Farzana Rowther、Tracy Warr、Timothy Snape

  DOI：10.1016/j.bmc.2013.01.032

  日期：2013.4

  A series of related 2-arylindoles have been evaluated for their anticancer activity against a range of glioblastoma cell lines using a number of different cell-based assays to determine cell viability after treatment with the compounds. The best indoles, which showed comparable activity to cisplatin against a U87MG cell line in the MTS assay, were taken forward and initial studies suggest that their mechanism of action is consistent with the generation of reactive oxygen species followed by autophagic cell death. Furthermore, activity was also observed in glioblastoma short-term cell cultures for the best lead compound and in some cases gave low micromolar IC(50)s. (C) 2013 Elsevier Ltd. All rights reserved.
• An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole
  作者：Anthony D. Alorati、Andrew D. Gibb、Peter R. Mullens、Gavin W. Stewart

  DOI：10.1021/op300303p

  日期：2012.12.21

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.