2-氧代-2-[4-(三氟甲氧基)苯基]乙醛 | 1060812-64-7

• 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: 2-氧代-2-[4-(三氟甲氧基)苯基]乙醛
• 英文名称: p-trifluoromethoxyphenyl glyoxal
• 英文别名: 4-trifluoromethoxyphenylglyoxal；2-Oxo-2-[4-(trifluoromethoxy)phenyl]acetaldehyde；2-oxo-2-[4-(trifluoromethoxy)phenyl]acetaldehyde
• CAS: 1060812-64-7
• 化学式: C₉H₅F₃O₃
• 分子量: 218.132
• InChiKey: BSHOHADAQXVHOC-UHFFFAOYSA-N

物化性质

• 沸点：
  223.8±40.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2-氧代-2-[4-(三氟甲氧基)苯基]乙醛 在 caesium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.42h， 生成 3,5-dichloro-N-(1-methyl-2-oxo-4-(4-(trifluoromethoxy)phenyl)-2,5-dihydro-1H-benzo[b][1,4]diazepin-3-yl)-N-phenethylbenzamide
  参考文献：
  名称：

  (Z)-Stereoselective Synthesis ofMono- andBis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction

  摘要：

  Several novel cascade reactions are herein reported that enable access to a variety of unique mono- and bis-heterocyclic scaffolds. The sequence of cascade events are mediated through acid treatment of an Ugi adduct that affords 1,5-benzodiazepines which subsequently undergo an elegant rearrangement to deliver (E)-benzimidazolones, which through acid-promoted tautomerization convert to their corresponding (Z)-isomers. Moreover, a variety of heterocycles tethered to (Z)-benzimidazole-2-ones are also accessible through similar domino-like processes, demonstrating a general strategy to access significantly new scaffold diversity, each containing four points of potential diversification. Final structures of five scaffolds have been definitively proven by X-ray crystallography.

  DOI：

  10.1021/acs.joc.5b00955
• 作为产物：
  描述：

  4-(三氟甲氧基)苯乙酮 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 2-氧代-2-[4-(三氟甲氧基)苯基]乙醛
  参考文献：
  名称：

  Rh(III)催化5-芳基吡嗪酮与炔烃的氧化环化合成π-扩展杂环

  摘要：

  报道了 5-芳基吡嗪酮和内部炔烃之间的 Rh(III) 催化的 C-H 官能化和随后的氧化环化。该协议通过 C(sp 2 )-H 烯基化和随后的环化提供了对各种吡嗪酮连接的萘的便捷访问。这种转化具有条件温和、简单、官能团相容性好的特点。值得注意的是，这是第一次使用吡嗪酮作为指导基团进行 C-H 官能化的报道。

  DOI：

  10.1021/acs.joc.1c01752

文献信息

• Ugi/Robinson–Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles
  作者：Arthur Y. Shaw、Zhigang Xu、Christopher Hulme

  DOI：10.1016/j.tetlet.2012.02.030

  日期：2012.4

  novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson–Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson–Gabriel cyclodehydration

  这封信公开了通过串联 Ugi/Robinson-Gabriel 序列一系列 2,4,5-三取代恶唑的新颖简明合成。在此，2,4-二甲氧基苄胺1用作氨当量，与芳基乙二醛3和支持Ugi试剂、异腈和羧酸组合。因此，酸处理的 Ugi 中间体的产物理想地配置为进行 Robinson-Gabriel 环脱水反应，以产生所需的恶唑支架5。
• Triethylamine-Promoted Henry Reaction/Elimination of HNO₂/Cyclization Sequence of Functionalized Nitroalkanes and 2-Oxoaldehydes: Diversity-Oriented Synthesis of Oxacycles
  作者：Yu-Xia Lu、Xue-Jiao Lv、Chang Liu、Yan-Kai Liu

  DOI：10.1021/acs.orglett.3c01158

  日期：2023.6.9

  The triethylamine-promoted cascade Henry reaction/elimination of HNO2/cyclization reaction of 2-oxoaldehydes with nitroalkanes bearing various remote functionalities is described. Both chiral and achiral nitroalkanes were applicable to this protocol, leading to a variety of oxacycles, such as chromenes, chromanes, cyclic hemiacetals, and polycyclic acetals. An unexpected regioselective photooxygenation

  描述了三乙胺促进的级联亨利反应/HNO 2的消除/2-氧代醛与带有各种远程官能团的硝基烷烃的环化反应。手性和非手性硝基烷烃均适用于该方案，从而产生各种氧杂环化合物，例如色烯、色烷、环状半缩醛和多环缩醛。在衍生化过程中，在没有敏化剂的情况下发生了意想不到的区域选择性光氧化，通过与单线态氧反应将衍生的二烯产物转化为二氧杂环丁烷，其在裂解后提供了 chromen-2-one 和苯甲醛。
• Successive Promotion of Formal [3+2] Cycloaddition of Aryl Methyl Ketones by I₂ and Zn: Access to 2-Hydroxy-4-morpholin-2,5-diarylfuran-3(2<i>H</i>)-ones with a Quaternary Carbon Center
  作者：Zhi-Cheng Yu、Xi Shen、You Zhou、Jin-Tian Ma、Xiang-Long Chen、Li-Sheng Wang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.3c00885

  日期：2023.7.7

  2-Hydroxy-4-morpholin-2,5-diarylfuran-3(2H)-one derivatives were constructed sequentially using iodine and zinc dust from simple and readily available methyl ketone and morpholine as the starting materials. Under mild conditions, C–C, C–N, and C–O bonds formed in a one-pot synthesis. A quaternary carbon center was successfully constructed, and the active drug fragment morpholine was introduced into the molecule

  以简单易得的甲基酮和吗啉为原料，使用碘和锌粉依次构建了2-羟基-4-吗啉-2,5-二芳基呋喃-3(2H ) -酮衍生物。在温和条件下，C-C、C-N 和 C-O 键在一锅合成中形成。成功构建了季碳中心，并将活性药物片段吗啉引入到分子中。
• A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles
  作者：Guillermo Martinez-Ariza、Muhammad Ayaz、Christopher Hulme

  DOI：10.1016/j.tetlet.2013.09.113

  日期：2013.12

  A straightforward procedure for the preparation of N-quinoxaline-indoles is presented. A base-catalyzed one-pot addition of indoles to a preformed alpha-iminoketone proceeds on the N-1 indole and the subsequent adduct undergoes an acid-mediated deprotection of an internal amino nucleophile, intramolecular cyclization, and final oxidation generating N-1-quinoxaline-indoles in good yield. (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] N-SUBSTITUTED-3-TRICYCLYL PIPERIDINE DERIVATIVES AS ANTICANCER AND NEUROPROTECTIVE AGENTS<br/>[FR] DÉRIVÉS DE 3-TRICYCLYL-PIPÉRIDINES N-SUBSTITUÉES UTILISÉS EN TANT QU'AGENTS ANTICANCÉREUX ET NEUROPROTECTEURS
  申请人：ICAHN SCHOOL MED MOUNT SINAI

  公开号：WO2021150700A1

  公开（公告）日：2021-07-29

  A genus of N-substituted-3-tricyclyl piperidine derivatives is disclosed. The compounds are of the following genus: The compounds induce FOXO1 transcription factor translocation to the nucleus by modulating PP2A and, as a consequence, exhibit anti-proliferative effects. They are useful in the treatment of a variety of disorders, including as a monotherapy in cancer treatment, or used in combination with other drugs to restore sensitivity to chemotherapy where resistance has developed.