2-溴-N-丁基苯胺 | 1019576-24-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-溴-N-丁基苯胺
• 英文名称: 2-bromo-N-butylaniline
• CAS: 1019576-24-9
• 化学式: C₁₀H₁₄BrN
• mdl: MFCD11144862
• 分子量: 228.132
• InChiKey: STECRESJQITXES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-N-丁基苯胺 、 4-异恶唑硼酸频哪醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以94%的产率得到1-butyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  在新型串联催化下高效构建各种3-氰基吲哚。

  摘要：

  已经开发了通过钯催化的串联反应的3-氰基吲哚的新颖和快速的构建。获得“ NH”无保护基的N-烷基和N-芳基3-氰基吲哚，收率为好至极好。这种合成方法的实用性通过成功合成实用化合物（例如治疗性雌激素受体配体A前体）得到进一步证明。机理研究表明，串联催化利用了Suzuki交叉偶联以及随后的碱诱导的异恶唑片段化，然后是醛亚胺缩合。

  DOI：

  10.1039/d0cc05439a
• 作为产物：
  描述：

  N-(2-bromophenyl)-4-methylbenzenesulfonamide 在 三氟甲磺酸 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 2-溴-N-丁基苯胺
  参考文献：
  名称：

  在酸性条件下磺酰胺的化学选择性脱保护：范围，磺酰基基团迁移和合成应用。

  摘要：

  磺酰胺与三氟甲磺酸的化学选择性酸性水解已被评估为一种脱保护方法，并进一步扩展到更复杂的合成应用中。与常规的麻烦的磺酰胺水解相反，发现接近化学计量的酸足以引起各种中性或电子缺陷的N-芳基磺酰胺的有效脱保护，而富电子的底物提供了磺酰基迁移产物。所开发的脱保护方法对N-芳基磺酰胺具有完全选择性，并且证明了区分各种不同磺酰胺的可能性。

  DOI：

  10.1021/acs.joc.7b02507

文献信息

• Palladium(II)/N-Heterocyclic Carbene-Catalyzed Regioselective Heteroannulation of Tertiary Propargyl Alcohols and<i>o</i>-Haloanilines to form 2-Alkenylindoles
  作者：Pradeep Kumar Reddy Panyam、Thirumanavelan Gandhi

  DOI：10.1002/adsc.201601349

  日期：2017.4.3

  Monometallic and bimetallic palladium(II)/N‐heterocyclic carbene complexes appended with naphthalimide or bisnaphthalimide moieties were designed, synthesized, and characterized. Employment of these catalysts brings about the step‐economic and regioselective heteroannulation of tertiary propargyl alcohols with o‐haloanilines resulting in biologically and pharmaceutically relevant 2‐alkenylindoles. Basis

  设计，合成和表征了单金属和双金属钯（II）/ N-杂环卡宾配合物，并附加了萘二甲酰亚胺或双萘二甲酰亚胺部分。这些催化剂的使用带来了叔炔丙醇与邻卤代苯胺的逐步经济和区域选择性杂成环化反应，从而产生了生物学上和药学上相关的2-烯基吲哚。通过在插入过程中炔丙基羟基部分与钯的配位，无法阐明区域选择性杂环化的基础。采用这种方法，可以通过后期修饰获得不对称的2,3-二取代吲哚的单一区域异构体。已经研究了将萘二甲酰亚胺或双萘二甲酰亚胺附加到NHC上对催化效率的作用。
• Selective N-Alkylation of Arylamines with Alkyl Chloride in Ionic Liquids: Scope and Applications
  作者：Antonio Monopoli、Pietro Cotugno、Marina Cortese、Cosima Damiana Calvano、Francesco Ciminale、Angelo Nacci

  DOI：10.1002/ejoc.201200202

  日期：2012.6

  An efficient N-selective alkylation of primary aromatic amines in molten quaternary ammonium salts, as the solvent, under relatively mild and base-free conditions is presented. On the basis of the Kamlet–Taft parameters and the nucleophilicity of the IL (ionic liquid) anions, the influence of the ionic liquid was evaluated. This protocol was validated on a larger multigram scale and with the syntheses

  介绍了在相对温和和无碱的条件下，以熔融季铵盐作为溶剂，伯芳胺的有效 N 选择性烷基化。在 Kamlet-Taft 参数和 IL（离子液体）阴离子的亲核性的基础上，评估了离子液体的影响。该协议在更大的多克规模上进行了验证，并与生物活性杂环（例如，1,4-苯并噻嗪和喹喔啉）和新的高效 MALDI 基质的合成有关。
• Chemoselective synthesis of tertiary and secondary amines by reductive amination of aldehydes
  作者：Wan-Jin Xiong、Lei Li、Jiang-Tao Li、Shi-Qiang Zhang、Jun-Lei Tang、Taigang Zhou

  DOI：10.1016/j.tetlet.2023.154684

  日期：2023.9

  A simple and efficient catalyst-free chemoselective reductive amination of primary amines and aldehydes to synthesis of tertiary and secondary amines with borane complex was developed. Primary amines are converted into tertiary and secondary amines in one pot reaction under mild condition with good functional group compatibility and It does not require any catalyst to participate in this reaction.

  开发了一种简单高效的无催化剂化学选择性还原胺化伯胺和醛，以与硼烷配合物合成叔胺和仲胺。伯胺转化为叔胺和仲胺的一锅反应条件温和，官能团相容性好，并且不需要任何催化剂参与该反应。通过改变硼烷络合物的空间位阻来实现化学选择性控制。该策略成功应用于合成丁卡因（麻醉剂），并通过同位素标记实验验证了其潜在机制。
• Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones
  作者：Nekane Barbero、Mónica Carril、Raul SanMartin、Esther Domínguez

  DOI：10.1016/j.tet.2008.05.072

  日期：2008.7

  The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of Cut and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• Regioselective and Stereoselective Pd-Catalyzed Intramolecular Arylation of Furans: Access to Spirooxindoles and 5<i>H</i>-Furo[2,3-<i>c</i>]quinolin-4-ones
  作者：Jianchao Liu、Hui Peng、Yongjie Yang、Huanfeng Jiang、Biaolin Yin

  DOI：10.1021/acs.joc.6b01774

  日期：2016.10.21

  Herein, we report regio- and stereoselective intramolecular direct arylations of N-(2-bromophenyl)-2-furancarboxamides 1 to produce spirooxindoles 2 and 5H-furo[2,3-c]quinolin-4-ones 3 under different reaction conditions. Specifically, in the presence of Pd(PPh3)(4) as a catalyst, PPh3 as a ligand, and K2CO3 as a base, substrates 1 underwent intramolecular alpha-arylation, possibly via a Heck insertion pathway, to provide 2, with the Zeta-isomer being favored. When the base was t-BuOLi and R-1 was an aryl group, the reaction favored Epsilon-2, possibly via an electrophilic palladation pathway. In contrast, in the presence of PdCl2 as a catalyst, (o-OMePh)(3)P as a ligand, and PivOH as an additive, substrates 1 underwent intramolecular beta-arylation to provide 3, possibly via a concerted metalation-deprotonation process.