2-溴-N-乙基苯胺 | 69083-47-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-溴-N-乙基苯胺
• 中文别名: N-乙基-2-溴苯胺
• 英文名称: 2-bromo-N-ethylaniline
• 英文别名: (2-bromophenyl)ethylamine；N-Ethyl-2-bromo-benzenamine
• CAS: 69083-47-2
• 化学式: C₈H₁₀BrN
• mdl: MFCD11144863
• 分子量: 200.078
• InChiKey: FLRJSHVTNSVDDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-乙基苯胺 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醚 、 环己烷 、 水 为溶剂， 反应 26.17h， 生成 1-ethyl-3-(2-methylbutyl)-1H-indole
  参考文献：
  名称：

  Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes

  摘要：

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

  DOI：

  10.1021/jo048723e
• 作为产物：
  描述：

  N-(2-bromophenyl)ethanimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以207.6 mg的产率得到2-溴-N-乙基苯胺
  参考文献：
  名称：

  Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.05.072

文献信息

• Alanine triazole iridium-catalyzed C–N bond formation through borrowing hydrogen strategy
  作者：Xiaoli Yu、Ranran Zhao、Huida Wan、Yongchun Yang、Dawei Wang

  DOI：10.1016/j.tetlet.2016.08.093

  日期：2016.10

  An efficient synthesis of secondary amines has been described through alanine triazole iridium-catalyzed C–N bond formation of an aromatic amine and an alkyl amine using the borrowing hydrogen strategy. In addition, it was observed that alanine triazole iridium is also an efficient catalyst to promote C–N bond formation of an aromatic amine and alcohols with good to excellent yields.

  已经描述了通过借用氢策略通过丙氨酸三唑铱催化的芳香胺和烷基胺的C-N键形成形成仲胺的有效方法。此外，已观察到丙氨酸三唑铱也是一种有效的催化剂，可促进芳香胺和醇的C–N键形成，收率良好至极佳。
• Ru‐Catalyzed Deoxygenative Transfer Hydrogenation of Amides to Amines with Formic Acid/Triethylamine
  作者：Yixiao Pan、Zhenli Luo、Xin Xu、Haoqiang Zhao、Jiahong Han、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1002/adsc.201900406

  日期：2019.8.21

  ruthenium(II)‐catalyzed deoxygenative transfer hydrogenation of amides to amines using HCO2H/NEt3 as the reducing agent is reported for the first time. The catalyst system consisting of [Ru(2‐methylallyl)2(COD)], 1,1,1‐tris(diphenylphosphinomethyl) ethane (triphos) and Bis(trifluoromethane sulfonimide) (HNTf2) performed well for deoxygenative reduction of various secondary and tertiary amides into the corresponding

  首次报道了使用HCO 2 H / NEt 3作为还原剂的钌（II）催化的酰胺脱氧转移胺成胺。催化剂体系由[Ru（2-甲基烯丙基）2（COD）]，1,1,1-三（二苯基膦甲基）乙烷（triphos）和双（三氟甲烷磺酰亚胺）（HNTf 2）在将各种仲酰胺和叔酰胺脱氧还原成相应的胺方面表现出色，选择性极好，并且对包括还原敏感基团在内的官能团表现出很高的耐受性。氢源和酸助催化剂的选择对于催化至关重要。机理研究表明，通过借入氢对原位生成的醇和胺进行还原胺化是主要途径。
• Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-<i>N</i> -Alkylation of Primary Amides and Arylamines
  作者：Ryu Sakamoto、Shunya Sakurai、Keiji Maruoka

  DOI：10.1002/chem.201702217

  日期：2017.7.6

  alkylsilyl peroxides as alkylating agents is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the alkylsilyl peroxides, as well as to the primary amides and arylamines. Mechanistic studies suggest that the present reaction should proceed through a free-radical process that includes alkyl radicals generated from the alkylsilyl peroxides.

  报道了使用烷基甲硅烷基过氧化物作为烷基化剂的伯酰胺或芳基胺的铜催化的选择性单-N-烷基化。该反应在温和的反应条件下进行，并且相对于烷基甲硅烷基过氧化物以及伯酰胺和芳基胺表现出广泛的底物范围。机理研究表明，本反应应通过自由基过程进行，该自由基过程包括由烷基甲硅烷基过氧化物产生的烷基。
• Palladium-catalyzed dearomatizing 2,5-alkoxyarylation of furan rings: diastereospecific access to spirooxindoles
  作者：Jianchao Liu、Xiaobing Xu、Jiuyi Li、Bo Liu、Huanfeng Jiang、Biaolin Yin

  DOI：10.1039/c6cc04298h

  日期：——

  .A protocol for Pd-catalyzed intra- and intermolecular 2,5-alkoxyarylation reactions of furans to diastereospecifically synthesize two series of spirooxindoles is reported. This protocol likely involves an intramolecular dearomatizing Heck-type [small alpha]-arylation of...

  报道了Pd催化呋喃的分子内和分子间2,5-烷氧基化反应以非对映特异性合成两个系列螺硫醇的方案。该方案可能涉及分子内脱芳香化的Heck型[小α]芳基化。
• 一种2,2′-联氮-双(3-烷基苯并噻唑啉-6-磺酸)盐的制备方法
  申请人：苏州亚科科技股份有限公司

  公开号：CN111892554B

  公开（公告）日：2022-08-16

  本发明公开了一种2,2'‑联氮‑双(3‑烷基苯并噻唑啉‑6‑磺酸)盐的制备方法，该制备方法所使用的原料容易获得，且价格低，能够在保证高反应收率的情况下，大幅度地降低生产的成本，从而有利于放大生产,同时，本发明所述的制备方法是不同于以往的新的制备工艺，该新的制备工艺将有助于本领域中ABTS的学术研究、产业化研究和实践，从而促进本领域相关技术和相关产业经济的发展。