叔丁基 (2,3-二氢苯并[b][1,4]二噁英-6-基)氨基甲酸酯 | 652153-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 叔丁基 (2,3-二氢苯并[b][1,4]二噁英-6-基)氨基甲酸酯
• 中文别名: 叔丁基(2,3-二氢苯并[b][1,4]二噁英-6-基)氨基甲酸酯
• 英文名称: (2,3-dihydrobenzo[1,4]dioxin-6-yl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl 2,3-dihydrobenzo[b][1,4]dioxin-6-ylcarbamate；tert-Butyl (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)carbamate；tert-butyl N-(2,3-dihydro-1,4-benzodioxin-6-yl)carbamate
• CAS: 652153-62-3
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: ZVSUCCPFCVDFDL-UHFFFAOYSA-N

物化性质

• 沸点：
  309.7±41.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  叔丁基 (2,3-二氢苯并[b][1,4]二噁英-6-基)氨基甲酸酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-((5-(4-((2,3-dihydro-1,4-benzodioxin-6-yl)amino)-1,3,5-triazin-2-yl)-3-pyridinyl)amino)-1-propanol
  参考文献：
  名称：

  Synthesis and Identification of [1,3,5]Triazine-pyridine Biheteroaryl as a Novel Series of Potent Cyclin-Dependent Kinase Inhibitors

  摘要：

  On the basis of previous studies, we identified pyrazine-pyridine A as a potent vascular endothelial growth factor inhibitor and pyrimidine-pyridine B as a moderately potent cyclin dependent kinase (CDK) inhibitor. A proposed combination of CGP-60474 and compound B led to the discovery of [1,3,5]triazine-pyridine as a new series of potent CDK inhibitors. Palladium-catalyzed C-C bond formation reactions, particularly the Negishi coupling reaction, were used to assemble various triazine-heteroaryl analogues effectively. Among them, compound 20 displayed high inhibitory potency at CDK1 IC50 = 0.021 mu M), CDK2, and CDK5 and submicromolar potency at CDK4, CDK6, and CDK7. Compound 20 also displayed high potency at GSK-3 beta. It demonstrated potent antiproliferative activity on various tumor cell lines, including HeLa, HCT-116, U937, and A375. When 20 was administered intraperitoneally at 150 and 125 mg/kg to nude mice bearing human A375 xenografts, the compound produced a significant survival increase. Molecular docking studies were conducted in an attempt to enhance the understanding of the observed structure-activity relationship.

  DOI：

  10.1021/jm040214h
• 作为产物：
  描述：

  tert-butyl 2,3-dihydrobenzo[b][1,4]dioxin-6-yl(3-perfluorooctylpropoxy)carbamate 在 甲醇 、 三羰基三(丙腈)钼(O) 作用下， 反应 0.25h， 以91%的产率得到叔丁基 (2,3-二氢苯并[b][1,4]二噁英-6-基)氨基甲酸酯
  参考文献：
  名称：

  使用含氟标记的氨等效物对芳基碘进行胺化

  摘要：

  描述了用于芳基碘化物的 Cu 催化胺化的氟标记氨等价物，其中 N-Boc 保护的苯胺以高总产率和纯度生产。所有纯化步骤均使用氟固相萃取 (F-SPE) 进行，大大简化并加快了所需产物的分离。

  DOI：

  10.1002/ejoc.201000367

文献信息

• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。
• [EN] A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS<br/>[FR] LIGAND POLYVALENT POUR DES FONCTIONNALISATIONS DE MÉTA-C-H CATALYSÉES PAR DU PALLADIUM
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2017184589A1

  公开（公告）日：2017-10-26

  A class of mono-protected 3-amino-2- hydroxypyridine (MPAHP) ligands that enable the meta- C-H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C-H functionalization processes is also illustrated by the development of a meta-C-H amination reaction and a meta-C-H alkynylation reaction.

  一种单保护的3-氨基-2-羟基吡啶（MPAHP）配体类别，能够利用去环戊烯作为瞬时介质，实现苯胺、酚、苯乙酸和生物相关杂环化合物的间位C-H芳基化。该间位芳基化方法在制药行业中的适用性通过对杂环底物和杂环碘化合物的示例进行说明，这一成就得益于使用MPAHP配体。MPAHP配体的启用性质还通过开发间位C-H氨化反应和间位C-H炔基化反应来展示其实现其他间位C-H官能化过程的能力。
• [EN] SUBSTITUTED TRIAZINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DES KINASES A BASE DE TRIAZINE SUBSTITUEE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004009562A1

  公开（公告）日：2004-01-29

  The present invention provides substituted 1,3,5-triazine compounds as kinase inhibitors and a method for treating or ameliorating a kinase mediated disorder.

  本发明提供了替代的1,3,5-三嗪化合物作为激酶抑制剂，并提供了一种治疗或改善激酶介导的疾病的方法。
• [EN] ANTIBACTERIAL OXAZOLONE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXAZOLONE ANTIBACTÉRIENS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2014108832A1

  公开（公告）日：2014-07-17

  The invention relates to antibacterial compounds of formula (I): wherein U represents CH or N; V represents CH or N, provided that at least one of U and V does not represent N; R represents H, halogen, methyl, methoxy, cyano or ethynyl; either W represents a phenyl group substituted in para position with (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)thioalkoxy and optionally in meta position with halogen, or W is a group having one of the formulae W1 and W2 below: W1 w2 wherein Q is O or S and X is CH or N; and salts of such compounds.

  该发明涉及式(I)的抗菌化合物：其中U代表CH或N；V代表CH或N，但至少其中一个不代表N；R代表H、卤素、甲基、甲氧基、氰基或乙炔基；W要么代表一个苯基，该苯基在对位上被(C1-C3)烷基、(C1-C3)氧基或(C1-C3)硫氧烷基取代，且在间位上可选地被卤素取代，要么W是具有下列W1和W2式之一的基团：W1 w2 其中Q为O或S，X为CH或N；以及这些化合物的盐。
• Synthesis of 6-methylphenanthridines and evaluation against human papillomavirus-related endocervical adenocarcinoma (KB 3.1) cells
  作者：Hichem Maslah、Charles Skarbek、Raphaël Labruère

  DOI：10.1016/j.phytol.2023.02.012

  日期：2023.4