2-溴-3-(羟甲基)-1-硝基苯 | 90407-20-8

• 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: 2-溴-3-(羟甲基)-1-硝基苯
• 英文名称: 2-bromo-3-nitrobenzyl alcohol
• 英文别名: (2-Bromo-3-nitrophenyl)methanol
• CAS: 90407-20-8
• 化学式: C₇H₆BrNO₃
• 分子量: 232.034
• InChiKey: XWMVYVPXQRUCMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-3-(羟甲基)-1-硝基苯 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 potassium tert-butylate 、 四丁基氟化铵 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.42h， 生成 N-(2-bromo-3-(2-methoxyvinyl)phenyl)acetamide
  参考文献：
  名称：

  A Pd(0)-Mediated Indole (Macro)cyclization Reaction

  摘要：

  Herein we report a systematic study of the Larock indole annulation designed to explore the scope and define the generality of its use in macrocyclization reactions, its use in directly accessing the chloropeptin I versus II DEF ring system as well as key unnatural isomers, its utility for both peptide-derived and more conventional carbon-chain based macrocycles, and its extension to intramolecular cyclizations with formation of common ring sizes. The studies define a powerful method complementary to the Stile or Suzuki cross-coupling reactions for the synthesis of cyclic or macrocyclic ring systems containing an embedded indole, tolerating numerous functional groups and incorporating various (up to 28-membered) ring sizes. As a result of the efforts to expand the usefulness and scope of the reaction, we also disclose a catalytic variant of the reaction, along with a powerful Pd-2(dba)(3)-derived catalyst system, and an examination of the factors impacting reactivity and catalysis.

  DOI：

  10.1021/ja3121394
• 作为产物：
  描述：

  2-溴-1-(溴甲基)-3-硝基苯 在 水 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 336.0h， 以93%的产率得到2-溴-3-(羟甲基)-1-硝基苯
  参考文献：
  名称：

  Synthesis of Indoles Isolated from Tricholoma Species

  摘要：

  DOI：

  10.1021/jo991208+

文献信息

• Tandem radical cyclisations : Synthesis of lysergic acid derivatives
  作者：Yusuf Özlü、David E. Cladingboel、Philip J. Parsons

  DOI：10.1016/s0040-4020(01)85078-x

  日期：1994.2

  A novel free radical cyclisation approach for the synthesis of lysergic acid analogues has been investigated. The homolytic cleavage of carbon-bromine bond, mediated by tri-n-butyltin hydride, led to the development of a method for the construction of 3,4-disubstituted dihydroindoles via single cyclisation; hexahydrobenz[cd]indoles via double tandem cyclisations and both octahydroindolo[6,5,4-cd]indoles

  已经研究了用于合成麦角酸类似物的新颖的自由基环化方法。由三正丁基锡氢化物介导的碳-溴键的均相裂解导致开发了一种通过单环化反应构建3,4-二取代的二氢吲哚的方法。经由双串联环化的六氢苯并[cd]吲哚和经由三自由基环化的八氢吲哚[6,5,4-cd]吲哚和十氢吲哚[4,3-fg]喹啉。由N-3- [3-（N-乙酰基-N-烯丙基氨基）-2-溴苯基] -5-（羰基甲氧基）-1生成的芳基的成功串联双5-exo-trig，6-endo-trig环化反应，4，5，6-四氢-N-甲基吡啶提供了甲基1-乙酰基-2，3，9，10-四氢丝氨酰。
• Metal–Organic Framework‐Encapsulated CoCu Nanoparticles for the Selective Transfer Hydrogenation of Nitrobenzaldehydes: Engineering Active Armor by the Half‐Way Injection Method
  作者：Yang Li、Yu‐Nong Li、Jian‐wei Zheng、Xiao‐yun Dong、Rong‐xiu Guo、Yi‐ming Wang、Ze‐nan Hu、Yongjian Ai、Qionglin Liang、Hong‐bin Sun

  DOI：10.1002/chem.202003857

  日期：2021.1.13

  selective transfer hydrogenation of nitrobenzaldehydes into corresponding nitrobenzyl alcohols in high selectivity (99 %) and conversion (99 %) rather than nitro group reduction products. Notably, this method achieves the precise assembly of a MOF‐encapsulated composite, and the ingenious combination of MOF and nanoparticles exhibits excellent catalytic performance in the selective hydrogen transfer reaction

  由金属-有机骨架（MOF）封装的具有Fe 3 O 4核（Fe 3 O 4 @SiO 2 -NH 2 -CoCu @ UiO-66）的新型盔甲型复合材料CoCu纳米粒子已通过设计和合成。半注入法，成功地用作选择性转移氢化的有效且可回收的催化剂。在这种中途注入方法中，合成前的Fe 3 O 4 @SiO 2 -NH 2在MOF萌芽期的中途，将CoCo注入UiO-66前体溶液中。形成的MOF装甲可以起到以下作用：除CoCu纳米颗粒外，还提供大量其他催化位点，保护CoCu纳米颗粒并提高催化剂稳定性，从而促进硝基苯甲醛以高选择性（99％）和转化率选择性转移氢化为相应的硝基苄醇（ 99％）而不是硝基还原产物。值得注意的是，该方法可实现MOF封装复合材料的精确组装，并且MOF和纳米颗粒的巧妙结合在选择性氢转移反应中显示出出色的催化性能，在催化中实现了“ 1 + 1> 2”策略。
• Fast microwave promoted palladium-catalyzed synthesis of phthalides from bromobenzyl alcohols utilizing DMF and Mo(CO) 6 as carbon monoxide sources
  作者：Xiongyu Wu、A.K. Mahalingam、Yiqian Wan、Mathias Alterman

  DOI：10.1016/j.tetlet.2004.04.110

  日期：2004.6

  utilizing in situ generated CO for the synthesis of phthalides has been developed. DMF and Mo(CO)6 were applied as two alternative CO-sources in these microwave promoted carbonylation–lactone formation reactions. Mo(CO)6 was found to be the more generally applicable CO-source and provided phthalides as well as dihydroisocoumarin, dihydroisoindone, and phthalimide from the corresponding aryl bromide via

  已经开发了一种利用原位生成的CO合成邻苯二甲酸盐的快速方法。在这些微波促进的羰基化-内酯形成反应中，DMF和Mo（CO）6被用作两种替代的CO源。发现Mo（CO）6是更普遍适用的CO源，并通过在1小时反应时间内通过有效的CO插入而从相应的芳基溴化物中提供了邻苯二甲酸酯以及二氢异香豆素，二氢异茚酮和邻苯二甲酰亚胺。
• [EN] 1-BENZYL-5-PIPERAZIN-1-YL-3,4 DIHYDRO-1H-QUINAZOLIN-2-ONE DERIVATIVES AND THE RESPECTIVE 1H-BENZO(1,2,6)THIADIAZINE-2,2-DIOXIDE AND 1,4-DIHYDRO-BENZO(D) (1,3)OXAZIN-2-ONE DERIVATIVES AS MODULATORS OF THE 5-HYDROXYTRYPTAMINE RECEPTOR (5-HT) FOR THE TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM<br/>[FR] DERIVES DE 1-BENZYL-5-PIPERAZIN-1-YL-3,4 DIHYDRO-1H-QUINAZOLIN-2-ONE ET DERIVES DE 1H-BENZO(1,2,6)THIADIAZINE-2,2-DIOXYDE ET DE 1,4-DIHYDRO-BENZO(D) (1,3)OXAZIN-2-ONE RESPECTIFS, UTILISES COMME MODULATEURS DU RECEPTEUR DE LA 5-HYDROXYTRYPTAMINE (5-HT) POUR LE TRAITEMENT D'AFFECTIONS DU SYSTEME NERVEUX CENTRAL
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005067933A1

  公开（公告）日：2005-07-28

  The invention relates to substituted quinazolinone compunds of formula (I) or a pharmaceutically acceptable salt thereof, wherein Y is C or S; m is 1 when Y is C and m is 2 when Y is S; n is 1 or 2; p is from 0 to 3; q is from 1 to 3; Z is -(CRaRb)r- or -SO2-, wherein r is from 0 to 2 and each of Ra and Rb is independently hydrogen or alkyl; X is CH or N; R2 is optionally substituted aryl or optionally substituted heteroaryl; preferably R2 is aryl, and more preferably phenyl optionally substituted by one or more trifluoromethyl, halo, cyano, C1-C6 alkyl or C1-C6 alkoxy; A is -NR3- or -O- wherein R3 is: hydrogen; alkyl, acyl, amidoalkyl, hydroxyalkyl or alkoxyalkyl; the other substituents are defined in the claims. The compounds are modulators of the 5-hydroxytryptamine receptor and are useful for the treatment of diseases of the central nervous system such as psychoses, schizophrenia, manic depressions, neurological disorders, memory disorders, attention deficit disorder, Parkinson’s disease, amyotrophic lateral sclerosis, Alzheimer’s disease, food uptake disorders, and Huntington’s disease.

  该发明涉及式(I)的取代喹唑啉酮化合物或其药学上可接受的盐，其中Y为C或S；当Y为C时，m为1，当Y为S时，m为2；n为1或2；p为0到3；q为1到3；Z为-(CRaRb)r-或-SO2-，其中r为0到2，Ra和Rb各自独立地为氢或烷基；X为CH或N；R2为可选择地取代的芳基或可选择地取代的杂环烷基；优选R2为芳基，更优选为苯基，可选地取代为一个或多个三氟甲基，卤素，氰基，C1-C6烷基或C1-C6烷氧基；A为-NR3-或-O-，其中R3为：氢；烷基，酰基，酰胺烷基，羟基烷基或烷氧基烷基；其他取代基在权利要求中定义。这些化合物是5-羟色胺受体的调节剂，可用于治疗中枢神经系统疾病，如精神病、精神分裂症、躁郁症、神经系统疾病、记忆障碍、注意力缺陷障碍、帕金森病、肌萎缩侧索硬化症、阿尔茨海默病、摄食障碍和亨廷顿病。
• Silver-Mediated Synthesis of Substituted Benzofuran- and Indole-Pyrroles via Sequential Reaction of <i>ortho</i>-Alkynylaromatics with Methylene Isocyanides
  作者：Jian-Quan Liu、Xinyi Chen、Andrey Shatskiy、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.joc.9b00528

  日期：2019.7.19

  -yl)phenols or 2-ethynyl-3-(1-hydroxyprop-2-yn-1-yl)anilines and methylene isocyanides has been developed. A sequential 5-endo-dig cyclization and [3 + 2] cycloaddition process is proposed. This synthetic strategy is atom- and step-efficient and applicable to a broad scope of substrates, allowing the synthesis of valuable substituted benzofuran- and indole-pyrroles in moderate to high yields.

  2-乙炔基-3-（1-羟基丙-2-yn-1-基）苯酚或2-乙炔基-3-（1-羟基丙-2-yn-1-基）苯胺与亚甲基异氰化物之间的银介导反应已经被开发出来。提出了一个顺序的5- endo - dig环化和[3 + 2]环加成过程。这种合成策略具有原子效率和分步效率，适用于广泛范围的底物，可以中等至高收率合成有价值的取代苯并呋喃和吲哚吡咯。