2-benzoyl-3-(3-bromophenyl)but-2-enenitrile | 1146188-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 2-benzoyl-3-(3-bromophenyl)but-2-enenitrile
• CAS: 1146188-86-4
• 化学式: C₁₇H₁₂BrNO
• 分子量: 326.192
• InChiKey: GERJYSOYBSVOFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.8±45.0 °C(predicted)
• 密度：
  1.384±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(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-(3-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-(3-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：

  苯甲酰乙腈 、 3'-溴苯乙酮 在 四氯化钛 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-benzoyl-3-(3-bromophenyl)but-2-enenitrile
  参考文献：
  名称：

  Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β′-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine

  摘要：

  Two classes of phosphine-catalyzed addition/cycloaddition domino reactions of beta'-acetoxy allenoate 1 have been developed. The reaction of 1 with 2-acyl-3-methyl-acrylonitrile 2 readily occurs to give 2-oxabicyclo[3.3.1]nonane 3, furnishing the beta'-addition/[4 + 4] cycloaddition domino sequence. In this sequence, beta'C of allenoate 1 is an electrophilic center, and its beta'C and gamma C serve as a 1,4-dipole. When the other reaction partner is switched to 2-acyl-3-(2-pyrrole)-acrylonitrile 8, a gamma-addition/[3 + 2] cycloaddition domino reaction is instead observed, in which allenoate 1 exhibits dual electrophilic reactivity of gamma C and 1,3-dipole chemical behavior of beta C and beta'C. Furthermore, both of these two asymmetric variants have also been achieved with up to 93% ee. The domino reactions presented in this report are valuable for highly stereoselective construction of complex structures under mild reaction conditions.

  DOI：

  10.1021/jacs.5b03273

文献信息

• Phosphine-Catalyzed Enantioselective [4 + 2] Cycloaddition–Semipinacol-Type-Rearrangement Reaction of Morita–Baylis–Hillman Carbonates
  作者：Yuan Zhong、Xiaoyun Zhao、Lu Gan、Sihua Hong、Xianxing Jiang

  DOI：10.1021/acs.orglett.8b01661

  日期：2018.7.20

  The chiral phosphine-triggered electrophilic ylide intermediate for a Morita–Baylis–Hillman carbonates activation strategy provides a promising method for the design of organocatalytic intermolecular higher-order annulation processes.

  Morita–Baylis–Hillman碳酸盐活化策略的手性膦触发的亲电性叶立德中间体为有机催化分子间高阶环化工艺的设计提供了一种有前途的方法。