1-(4-bromophenyl)-2-(imidazolidin-2-ylidene)ethanone | 82100-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-bromophenyl)-2-(imidazolidin-2-ylidene)ethanone
• 英文别名: 1-(4-Bromophenyl)-2-imidazolidin-2-ylideneethanone
• CAS: 82100-22-9
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: FSXWMFXMSFPEII-UHFFFAOYSA-N

物化性质

• 熔点：
  275 °C(Solv: N,N-dimethylformamide (68-12-2); ethanol (64-17-5))
• 沸点：
  402.1±45.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-2-(imidazolidin-2-ylidene)ethanone 以77%的产率得到
  参考文献：
  名称：

  Wang Li-Ben, Yu Chu-Yi, Huang Zhi-Tang, Synth. Commun., 25 (1995) N 9, S 1353-1358

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯甲酰乙腈 在 盐酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 30.0h， 生成 1-(4-bromophenyl)-2-(imidazolidin-2-ylidene)ethanone
  参考文献：
  名称：

  Synthesis of 2-(Benzoylmethylene)imidazolidines and -hexahydropyrimidines by Condensation of Ethyl Benzoylacetimidates With 1,2-Ethanediamine or 1,3-Propandiamine, and Some Addition Reactions

  摘要：

  苯甲酰乙酰亚胺酸乙酯与 1,2-乙二胺或 1,3-丙二胺在绝对乙醇中发生反应，分别生成 2-（苯甲酰亚甲基）咪唑烷或六氢嘧啶。光谱数据证实了这些产物的烯酮胺结构。此外，还介绍了盐酸和重氮二甲酸二乙酯与烯酮氨基化合物的亲电加成。

  DOI：

  10.1055/s-1987-27942

文献信息

• A facile synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines through NHC-catalyzed cascade annulations
  作者：Changsheng Yao、Weihui Jiao、Zhaoxin Xiao、Yuanwei Xie、Tuanjie Li、Xiangshan Wang、Rui Liu、Chenxia Yu

  DOI：10.1039/c3ra41935e

  日期：——

  A new efficient approach for the synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines with biological significance was successfully developed through a NHC-catalyzed cascade C–C bond and C–N bond formation process. This new alternative approach for the assembly of these multi-functionalized nitrogen bridgehead-fused heterocycles features mild conditions

  通过NHC催化的级联反应成功开发了一种新的高效合成四氢咪唑并[1,2- a ]吡啶和四氢苯并[ b ]咪唑并[1,2,3- ij ] [1,8]萘啶的新方法C–C键和C–N键的形成过程。组装这些多功能氮桥头稠合杂环的这种新的替代方法具有温和的条件，中等至高收率和操作简便性。
• Synthesis of Partially Reduced Imidazo[1,2-a]pyridines through an Unprecedented Base-Mediated (4+2) Cyclization
  作者：Ramendra Pratap、Rahul Panwar、Surjeet Singh、Pratik Yadav、Ranjay Shaw、Abhinav Kumar

  DOI：10.1055/s-0036-1588943

  日期：——

  A water-mediated regioselective synthesis of 6,7-diaryl-5-oxo-2,3,5,6-tetrahydroimidazo[1,2-a]pyridine-6-carbonitriles was performed by the reaction of 2-[1-cyano-2,2-bis(methylsulfanyl)vinyl]benzonitrile with 1-aryl-2-(imidazolidin-2-ylidene)ethanones under basic conditions. This reaction involves an unprecedented (4+2) annulation.

  6,7-diaryl-5-oxo-2,3,5,6-tetrahydroimidazo[1,2-a]pyridine-6-carbonitriles 的水介导区域选择性合成是通过 2-[1-cyano -2,2-双(甲基硫烷基)乙烯基]苄腈与1-芳基-2-(咪唑烷-2-亚基)乙酮在碱性条件下。该反应涉及前所未有的 (4+2) 环化。
• A new rapid multicomponent domino heteroannulation of heterocyclic keteneaminals: solvent-free regioselective synthesis of functionalized benzo[g]imidazo[1,2-a]quinolinediones
  作者：Li-Rong Wen、Qi-Chang Sun、Hai-Liang Zhang、Ming Li

  DOI：10.1039/c2ob27137k

  日期：——

  A highly efficient and straightforward three-component cascade reaction was developed to synthesize benzo[g]imidazo[1,2-a]quinolinedione derivatives from heterocyclic ketene aminals (HKAs), aldehydes, and 2-hydroxy-1,4-naphthoquinone (HNQ) via Et3N-catalyzed tandem [3 + 2 + 1] annulation under solvent-free conditions. The reactions were very mild, convenient and highly regioselective to form new fused

  开发了一种高效，简单的三组分级联反应，以从杂环中合成苯并[ g ]咪唑并[1,2- a ]喹啉二酮衍生物烯酮 缩醛（HKA），醛和 2-羟基-1,4-萘醌（HNQ）通过Et 3 N催化的串联[3 + 2 +1]在无溶剂条件下进行环化。反应非常温和，方便并且具有高度区域选择性，以形成新的稠合四环靶分子。
• Synthesis of Imidazo[1,2-a]pyridines and Pyrido[1,2-a]pyrimidines in Water and their S_NAr Cyclizations
  作者：Langpoklakpam Gellina Chanu、Thokchom Prasanta Singh、Yong Ju Jang、Yong-Jin Yoon、Okram Mukherjee Singh、Sang-Gyeong Lee

  DOI：10.5012/bkcs.2014.35.4.994

  日期：2014.4.20

  2013Synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydropyrido[1,2-a] pyrimidines by a one-pot andthree component reaction of α-oxoketenedithioacetals, diamines and DMAD in water has been described.Different routes for accessing the desired compounds were examined and a few specially designed-substrateshave been utilized further to afford the new imidazo and pyrido fused [1,8] naphthyridine

  E-mail: [e-mail] 2013年9月4日接收，2013年10月11日接受已经描述了水中的α-氧代烯二硫代缩醛、二胺和 DMAD。研究了获得所需化合物的不同途径，并进一步利用了一些专门设计的底物，通过 S
• Selective Synthesis of Highly Functionalized Bicyclic Pyridinone and 1,3-Oxazinane Derivatives
  作者：Shi-Sheng Cui、Rong Huang、Da-Yun Luo、Sheng-Jiao Yan、Jun Lin

  DOI：10.1002/ejoc.201700283

  日期：2017.6.30

  3-oxazinane derivatives 4 have been synthesised via the regioselective condensation reaction of heterocyclic ketene aminals (HKAs) with ethyl 2-cyano-3,3-bis(methylthio)-acrylate or 2-(bis(methyl-thio)methylene)-malononitrile in xylene at refluxing temperature. The bicyclic pyridinone compounds 3 can be efficiently obtained using catalyst-free conditions whereas 1,3-oxazinane derivatives 4 are obtained

  通过杂环烯酮缩醛胺 (HKAs) 与 2-氰基-3,3-双(甲硫基)-丙烯酸乙酯的区域选择性缩合反应，合成了两种新型双环化合物，如吡啶酮 3 和 1,3-恶嗪烷衍生物 4 或2-(双(甲硫基)亚甲基)-丙二腈的二甲苯溶液，回流温度。双环吡啶酮化合物 3 可以在无催化剂条件下有效获得，而 1,3-恶嗪烷衍生物 4 在相同条件下通过加入 Cs2CO3 获得。该反应具有收率高、原料便宜、最终处理方便等优点。