N-(2-溴乙基)-苯甲酰胺 | 27110-61-8

• 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: N-(2-溴乙基)-苯甲酰胺
• 英文名称: N-(2-Bromo-ethyl)-benzamide
• 英文别名: N-(2-bromoethyl)benzamide
• CAS: 27110-61-8
• 化学式: C₉H₁₀BrNO
• mdl: MFCD00157849
• 分子量: 228.088
• InChiKey: WCTQETQDPVEMGT-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  380.7±25.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2-溴乙基)-苯甲酰胺 在 二氧化碳 、 氧气 、 高氯酸四乙基铵 作用下， 生成 1-苯甲酰基氮丙啶
  参考文献：
  名称：

  Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

  摘要：

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.

  DOI：

  10.1021/jo970308h
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 作用下， 生成 N-(2-溴乙基)-苯甲酰胺
  参考文献：
  名称：

  Gabriel; Stelzner, Chemische Berichte, 1895, vol. 28, p. 2933

  摘要：

  DOI：

文献信息

• One-pot triflic anhydride-mediated synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides and amines
  作者：Alyssa A. Ellsworth、Christina L. Magyar、Grace E. Hubbell、Chelsea C. Theisen、Daniel Holmes、R. Adam Mosey

  DOI：10.1016/j.tet.2016.08.040

  日期：2016.10

  A one-pot synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides has been developed. The reaction affords high yields of diverse 1,2-disubstituted 2-imidazolines from triflic anhydride-mediated dehydration of amides followed by installation of a primary amine.

  已经开发了由N-（2-卤代乙基）酰胺一锅合成1，2-二取代的2-咪唑啉。该反应从三氟甲磺酸酐介导的酰胺脱水，然后安装伯胺的方法中，可得到高产率的各种1,2-二取代的2-咪唑啉。
• Well-Defined Amidate-Functionalized N-Heterocyclic Carbene -Supported Rare-Earth Metal Complexes as Catalysts for Efficient Hydroboration of Unactivated Imines and Nitriles
  作者：Zeming Huang、Shaowu Wang、Xiancui Zhu、Qingbing Yuan、Yun Wei、Shuangliu Zhou、Xiaolong Mu

  DOI：10.1021/acs.inorgchem.8b02067

  日期：2018.12.17

  unactivated imines and nitriles were investigated, and it was found that these complexes displayed excellent activities as well as remarkable functional group compatibility for imine and nitrile substrates such as halo-, alkyl-, hydroxyl-, N,N-dimethylamino-, and nitro- substituents. Among those, the chemoselectivity for this reaction among the common unsaturated functional groups was achieved in the order

  四酰胺化物官能化的N-杂环卡宾（NHC）稀土类金属酰氨基配合物[（κ 2 -N，O-κ 1 -大号）2 REN（森达3）2 ]（大号= 1-（C 6 H ^ 5 Ç ═ONCH 2 CH 2）-3-（CH 3）3 c ^ 6 ħ 2（N（CH）2 NC））[RE =尔（1），Y（2），镝（3），钆（4）]由2当量（1-（C中的一个一锅反应合成6 ħ 5 C═ONHCH2 CH 2）-3-（CH 3）3 C 6 H 2-（N（CH）2 NCH））Br（H 2 L Br）与5当量的KN（SiMe 3）3，然后用1当量的KN（SiMe 3）3处理在-40°C下于四氢呋喃中的RECl 3。对这些配合物进行了充分表征，并研究了它们对未活化的亚胺和腈进行硼氢化的催化活性，发现这些配合物对亚胺和腈底物（如卤代，烷基，羟基，氮，氮-二甲基氨基和硝基取代基。其中，在当前的催化体系中，常见的不饱和官能团之间对
• Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive <i>Gem</i>-Cyanation–Phosphonylation of Secondary Amides
  作者：Ting-Ting Chen、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1021/acs.orglett.9b01257

  日期：2019.5.17

  A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a Tf2O-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol

  已经开发出一种新的方法来制备α-氨基-α-氰基膦酸酯。该方法的特征在于Tf 2 O介导的仲酰胺还原性双氰胺氰基化/膦酰基化。温和的反应条件，高的键形成效率，廉价的易得原料以及具有宽泛的官能团相容性的良好至优异的收率构成了该方法的主要优点。该协议可以以克为单位运行。
• Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides
  作者：Victor Adebomi、Mahesh Sriram、Xavier Streety、Monika Raj

  DOI：10.1021/acs.orglett.1c01622

  日期：2021.8.20

  secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C–N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation

  在这里，我们解决了仲酰胺位点选择性修饰的长期挑战，并提出了一种简单的两步、无金属方法来选择性地修饰含有多个伯酰胺和仲酰胺的分子中的特定仲酰胺。密度泛函理论 (DFT) 提供了对 C-N 键激活的深入了解。这项研究涵盖了肽后期修饰的独特化学进展，从而利用酰胺将各种官能团结合到天然和合成分子中。
• Alkenes from halides and epoxides by reductive eliminations with CrII complexes
  作者：J.K. Kochi、D.M. Singleton、L.J. Andrews

  DOI：10.1016/s0040-4020(01)92648-1

  日期：1968.1

  A variety of β-substituted alkyl halides and epoxides are reductively eliminated in high yields to alkenes by CrIIen at room temperature. The reducing agent is easily prepared in situ from chromous salts and ethylenediamine. Reductive elimination and protolytic reduction of β-substituted alkyl halides by chromous reagent proceed by similar mechanisms, and involve free radicals and alkylchromium species

  在室温下，Cr II en可以高产率将各种β-取代的烷基卤化物和环氧化物还原为烯烃。还原剂易于原位制备由亚铬盐和乙二胺组成。铬试剂对β-取代的烷基卤化物的还原消除和质子还原的过程类似，并且涉及自由基和烷基铬物种作为中间体。在前一种方法中，容易从β-取代的烷基铬中间体中除去β-取代基，例如羟基，苯氧基，乙酰氧基，甲苯磺酰基，溴，氯，氨基和三甲基铵基团，从而生成烯烃。仅与诸如氰基，苯甲酰胺基和邻苯二甲酰亚胺基团的β-取代基相比，烷基铬物种的质子还原是一个显着的竞争反应。讨论了确定基团对烷基铬物种的还原消除和蛋白水解还原的相对速率的影响的因素。β-溴和三甲基铵基团可增强卤素从卤代烷到铬离子的初始配体转移，从而形成自由基。假定这些基团的邻近基团参与均相分解过程以形成溴或三甲基铵桥连的烷基自由基作为中间体。铬II en是比Cr II更有效的还原剂，与前者相比，前者压缩了各种卤化物的相对反应活性。邻二碘苯被Cr