2-benzoyl-3-(4-bromophenyl)but-2-enenitrile | 1146188-85-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-benzoyl-3-(4-bromophenyl)but-2-enenitrile
• CAS: 1146188-85-3
• 化学式: C₁₇H₁₂BrNO
• 分子量: 326.192
• InChiKey: GSJTYZQUYZTVDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.3±45.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-(4-bromophenyl)but-2-enenitrile 在 sulfur 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2-amino-4-(4-bromophenyl)thiophen-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Allosteric Modulators of the Adenosine A₁ Receptor: Synthesis and Pharmacological Evaluation of 4-Substituted 2-Amino-3-benzoylthiophenes

  摘要：

  A series of 4-substituted 2-amino-3-benzoylthiophenes was screened using a functional assay of A A(1)AR-mediated phosphorylation of ERK 1/2 in intact CHO cells to identify both potential agonistic effects as well the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA. More detailed concentration-response experiments were subsequently performed on two compounds (9a and 9o) utilizing both the ERK 1/2 assay as well as a second assay of [S-35]GTP gamma S binding to activated G proteins.

  DOI：

  10.1021/jm9002582
• 作为产物：
  描述：

  4-溴苯乙酮 、 苯甲酰乙腈 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 2-benzoyl-3-(4-bromophenyl)but-2-enenitrile
  参考文献：
  名称：

  Allosteric Modulators of the Adenosine A₁ Receptor: Synthesis and Pharmacological Evaluation of 4-Substituted 2-Amino-3-benzoylthiophenes

  摘要：

  A series of 4-substituted 2-amino-3-benzoylthiophenes was screened using a functional assay of A A(1)AR-mediated phosphorylation of ERK 1/2 in intact CHO cells to identify both potential agonistic effects as well the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA. More detailed concentration-response experiments were subsequently performed on two compounds (9a and 9o) utilizing both the ERK 1/2 assay as well as a second assay of [S-35]GTP gamma S binding to activated G proteins.

  DOI：

  10.1021/jm9002582

文献信息

• N-Heterocyclic Carbene-Catalyzed Construction of 1,3,5-Trisubstituted Benzenes from Bromoenals and α-Cyano-β-methylenones
  作者：Chun-Lin Zhang、Song Ye

  DOI：10.1021/acs.orglett.6b03306

  日期：2016.12.16

  A direct and efficient approach to 1,3,5-trisubstituted benzenes has been developed via N-heterocyclic carbene-catalyzed [2 + 4] annulation of α-bromoenals and α-cyano-β-methylenones. The reaction worked well for both aryl- and alkylenones.

  通过N-杂环卡宾催化的[2 + 4]环抱α-溴烯醛和α-氰基-β-甲基烯酮，已经开发出直接有效的1,3,5-三取代苯的方法。该反应对于芳基和烷基烯酮都很好。
• N-Heterocyclic Carbene-Catalyzed Synthesis of Multi-Substituted Benzenes from Enals and α-Cyano-β-methylenones
  作者：Chun-Lin Zhang、Zhong-Hua Gao、Zhi-Qin Liang、Song Ye

  DOI：10.1002/adsc.201600531

  日期：2016.9.15

  An oxidative NHC‐catalyzed [2+4] annulation of enals and α‐cyano‐β‐methylenones was established for the rapid assembly of multi‐substituted benzenes.

  建立了氧化型NHC催化的[2 + 4]环烯和α-氰基-β-甲基烯酮环化反应，以快速组装多取代的苯。
• Direct Assembly of Polysubstituted Naphthalenes via a Tandem Reaction of Benzynes and α-Cyano-β-methylenones
  作者：Qiang Wang、Yi An、Guangfen Du、Zhi-Hua Cai、Bin Dai、Lin He

  DOI：10.1021/acs.joc.0c01975

  日期：2020.11.6

  A mild and transition-metal-free benzannulation reaction for the construction of the naphthalene skeleton has been described. Benzynes react with α-cyano-β-alkylenones through a tandem nucleophilic addition/cyclization/aromatization process to afford polysubstituted naphthalenes in 50–94% yields.

  已经描述了用于构建萘骨架的温和且无过渡金属的苯环反应。苯甲酮通过串联亲核加成/环化/芳构化过程与α-氰基-β-烷基烯酮反应，以50-94％的产率提供多取代的萘​​。
• N-Heterocyclic Carbene-Catalyzed Convenient Benzonitrile Assembly
  作者：Qianfa Jia、Jian Wang

  DOI：10.1021/acs.orglett.6b00844

  日期：2016.5.6

  The benzonitrile unit is widely found in natural products, pharmaceuticals, and agrochemicals. Synthesis of benzonitriles has received considerable interests from the chemical community over the last few decades. Present synthetic protocols mainly rely on the pre-existing benzene core to install a cyano moiety. A new NHC-catalyzed [4 + 2]-benzannulation protocol is reported to assemble the benzonitrile

  苯甲腈单元广泛用于天然产品，药品和农用化学品中。在过去的几十年中，苯甲腈的合成已引起化学界的广泛关注。当前的合成方案主要依赖于预先存在的苯核来安装氰基部分。据报道，一种新的NHC催化的[4 + 2]苯甲酰化方案可组装苄腈框架。
• DBU-Mediated Construction of 1,3,5-Trisubstituted Benzenes via Annulation of α,β-Unsaturated Carboxylic Acids and α-Cyano-β-methylenones
  作者：Chun-Lin Zhang、Zhao-Fei Zhang、Zi-Hao Xia、You-Feng Han、Song Ye

  DOI：10.1021/acs.joc.8b01740

  日期：2018.10.19

  A DBU-mediated synthesis of 1,3,5-trisubstituted benzenes was developed via the [2 + 4] annulation of in situ activated α,β-unsaturated carboxylic acids and α-cyano-β-methylenones. The dual role of DBU as Brønsted base and nucleophilic Lewis base is the key for the success of the reaction.

  通过原位活化的α，β-不饱和羧酸和α-氰基-β-甲基烯酮的[2 + 4]环空反应，开发了DBU介导的1,3,5-三取代苯的合成方法。DBU作为Brønsted碱和亲核Lewis碱的双重作用是反应成功的关键。