1-(2-nitro-1-phenyl-ethyl)-1H-benzotriazole | 134005-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(2-nitro-1-phenyl-ethyl)-1H-benzotriazole
• 英文别名: 1-(2-nitro-1-phenylethyl)-1H-benzo[d][1,2,3]triazole；1-(2-nitro-1-phenylethyl)-1H-benzo[1,2,3]triazole；1-(2-nitro-1-phenylethyl)benzotriazole
• CAS: 134005-06-4
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: OEKMDHAGFVNMCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-nitro-1-phenyl-ethyl)-1H-benzotriazole 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.34h， 生成 N-((1R*,2R*,3S*)-3-(1H-benzo[d][1,2,3]triazol-1-yl)-2-nitro-1,3-diphenylpropyl)-2,2,2-trifluoro-N-(4-methoxyphenyl)acetamide
  参考文献：
  名称：

  Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes

  摘要：

  The conjugate addition nitro-Mannich reactions of ethyl-beta-nitroacrylate (1) and beta-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conjugate addition nitro-Mannich reaction was unsuccessful except for the addition of alkoxides to 2 in alcohol as solvent. Isolation of the conjugate addition products followed by deprotonation with (BuLi)-Bu-n and treatment with a simple imine in the presence of TFA led to beta-nitroamine derived products. Products derived from 1 spontaneously cyclised in only a few examples and on the whole led to inherently unstable products. Products derived from 2 were isolated as their trifluoroacetamides, gave good yields of single diastereoisomers for aromatic and alkoxide nucleophiles and the structures were verified by single crystal X-ray crystallography. Products derived from amine nucleophiles were isolated in low yields while sulfur nucleophiles gave poor diastereoselectivities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.042
• 作为产物：
  描述：

  T406石油添加剂 、 β-硝基苯乙烯 以 二氯甲烷 为溶剂， 反应 30.0h， 以86%的产率得到1-(2-nitro-1-phenyl-ethyl)-1H-benzotriazole
  参考文献：
  名称：

  Uncatalysed intermolecular aza-Michael reactions

  摘要：

  简历 摘要 研究了活性烯烃与一级和二级胺的无催化剂反应，生成多种单氢胺化和双氢胺化产物，后者较为罕见且具有原创性。这些反应首先取决于亲核试剂的强度。温度和试剂的立体阻碍是控制这些氮杂迈克尔反应选择性的其他关键因素。尽管某些含氮杂环胺的亲核性较差，但它们仍能与不同的活性烯烃反应，生成有价值的中间体。这些结果倾向于表明，活性烯烃与多氮芳香环之间的氢键相互作用可能控制这些协同或完全共轭的氮杂迈克尔加成反应。 补充材料： 本文的补充材料以单独文件提供： mmc1.doc

  DOI：

  10.1016/j.crci.2012.11.001

文献信息

• Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones
  作者：Feng Han、Lei Yang、Zhen Li、Chungu Xia

  DOI：10.1039/c1ob06346d

  日期：——

  A series of acidic-functionalized ionic liquids were synthesized and applied to the hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones under solvent-free conditions. Notably, 1-methylimidazoliump-toluenesulfonic ([Hmim]OTs) was found to be the most efficient catalyst and could realize “homogeneous catalysis, two-phase separation”. Additionally, the catalytic system has wide substrate scope and good to excellent yields (up to 99%) could be obtained at room temperature.

  一系列酸性功能化的离子液体被合成并应用于无溶剂条件下氮、硫和氧亲核试剂对α,β-不饱和酮的加成反应。值得注意的是，1-甲基咪唑对甲苯磺酸（[Hmim]OTs）被发现是最有效的催化剂，并能实现“均相催化，两相分离”。此外，该催化体系具有广泛的底物适用范围，并且在室温下能够获得良好至极佳的产率（高达99%）。
• A Practical Synthesis of 1,2-Nitroamines by Michael Addition of N-Nucleophiles to Nitroalkenes
  作者：Raphaël Robiette、Jacqueline Marchand-Brynaert、Trieu-Van Tran、Alex Cordi、Bernard Tinant

  DOI：10.1055/s-0030-1258176

  日期：2010.9

  A practical method for the synthesis of α-nitroamines by Michael addition of azide to nitroalkene has been developed. This reaction proceeds in high yields under very mild conditions (phase-transfer catalysis) and is found to be general; good yields are obtained with both aryl and alkyl derivatives as well as with 1,1-di­substituted ones. azides - amines - Michael addition - nitroalkenes - nitro­amines

  已经开发了一种通过将叠氮化物迈克尔加成到硝基烯烃上来合成α-硝基胺的实用方法。该反应在非常温和的条件下（相转移催化）以高收率进行，被发现是普遍的。芳基和烷基衍生物以及1，1-二取代的衍生物均获得良好的产率。 叠氮化物-胺-迈克尔加成-硝基烯烃-硝基胺
• N-(1-benzotriazol-1-ylalkyl)amides, versatile .alpha.-amidoalkylation reagents. 1. .alpha.-Amidoalkylation of CH acids
  作者：Alan R. Katritzky、Juliusz Pernak、Wei Qiang Fan、Franciszek Saczewski

  DOI：10.1021/jo00014a020

  日期：1991.7

  N-(1-Benzotriazol-1-ylalkyl)amides 2, easily prepared from an amide and an aldehyde with benzotriazole, react smoothly with CH acids under mild conditions to give the alpha-amidoalkylation products in good yields. Benzotriazole aminals also react with CH acids in the presence of methyl iodide.
• Enantioselective Organocatalytic Michael Addition Reactions between <i>N</i>-Heterocycles and Nitroolefins
  作者：Jian Wang、Hao Li、Liansuo Zu、Wei Wang

  DOI：10.1021/ol0601794

  日期：2006.3.1

  A method for Michael addition of N-heterocycles to nitroolefins has been developed. The process is promoted by a cinchona alkaloid derivative to give Michael adducts in moderate to high enantioselectivities.
• KATRITZKY, ALAN R.;PERNAK, JULIUSZ;FAN, WEI-QIANG;SACZEWSKI, FRANCISZEK, J. ORG. CHEM., 56,(1991) N4, C. 4439-4443
  作者：KATRITZKY, ALAN R.、PERNAK, JULIUSZ、FAN, WEI-QIANG、SACZEWSKI, FRANCISZEK

  DOI：——

  日期：——