methyl 1-(4-bromophenyl)-2-methyl-3-phenylcycloprop-2-enecarboxylate | 1313370-80-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 1-(4-bromophenyl)-2-methyl-3-phenylcycloprop-2-enecarboxylate
• 英文别名: Methyl 1-(4-bromophenyl)-2-methyl-3-phenylcycloprop-2-ene-1-carboxylate
• CAS: 1313370-80-7
• 化学式: C₁₈H₁₅BrO₂
• 分子量: 343.22
• InChiKey: RTLZBTBBSMUGMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 methyl 1-(4-bromophenyl)-2-methyl-3-phenylcycloprop-2-enecarboxylate
  参考文献：
  名称：

  Silver Triflate-Catalyzed Cyclopropenation of Internal Alkynes with Donor-/Acceptor-Substituted Diazo Compounds

  摘要：

  Silver triflate was found to be an efficient catalyst for the cyclopropenation of internal alkynes using donor-/acceptor-substituted diazo compounds as carbenoid precursors. Highly substituted cyclopropenes, which cannot be synthesized directly via rhodium(II)-catalyzed carbenoid chemistry, can now be readily accessed.

  DOI：

  10.1021/ol201503j

文献信息

• Recyclable heterogeneous metal foil-catalyzed cyclopropenation of alkynes and diazoacetates under solvent-free mechanochemical reaction conditions
  作者：Longrui Chen、Devonna Leslie、Michael G. Coleman、James Mack

  DOI：10.1039/c8sc00443a

  日期：——

  cyclopropenation of terminal and internal alkynes under mechanochemical reaction conditions. This methodology enables the functionalization of a wide range of terminal or internal alkynes under ambient, aerobic, and solvent-free conditions. Finally, we have demonstrated a unique and versatile one-pot domino Sonogashira-cyclopropenation mechanochemical reaction for the formation of complex cyclopropenes.

  发现银和铜箔是在机械化学反应条件下用于末端炔烃和内部炔烃环丙烷化的有效，通用和选择性的非均相催化剂。这种方法可以在环境，好氧和无溶剂条件下使各种末端或内部炔烃官能化。最后，我们展示了一种独特而通用的一锅多米诺多米诺Sonogashira-环丙烷化机械化学反应，用于形成复杂的环丙烯。
• Silver‐Catalyzed Asymmetric Insertion into Phenolic O−H Bonds using Aryl Diazoacetates and Theoretical Mechanistic Studies
  作者：Shingo Harada、Koki Tanikawa、Haruka Homma、Chigaya Sakai、Tsubasa Ito、Tetsuhiro Nemoto

  DOI：10.1002/chem.201902126

  日期：2019.9.18

  into the O-H bond of phenols was developed. A homobinuclear silver complex with a chiral phosphorous ligand was created in situ from AgNTf2 and (S)-XylylBINAP (in a 2:1 mole ratio). Detailed mechanistic studies using combined experimental and computational techniques revealed that one silver atom center of the catalyst forms a silver carbene and another one works as a Lewis acid for the nucleophilic

  已开发了由供体-受体取代的重氮化合物生成的羧甲基银对苯酚的OH键的对映选择性插入反应。由AgNTf2和（S）-XylylBINAP（以2：1的摩尔比）原位产生具有手性磷配体的同双核银络合物。使用组合的实验和计算技术进行的详细机理研究表明，催化剂的一个银原子中心形成银卡宾，而另一个作为路易斯酸用于苯酚的亲核加成。两个抗衡阴离子，两个水分子和两个银原子协同介导随后的质子化事件，从而降低活化能并控制对映选择性，从而提供了一系列有价值的α-芳基-α-芳氧基酯。
• Silver Triflate-Catalyzed Cyclopropenation of Internal Alkynes with Donor-/Acceptor-Substituted Diazo Compounds
  作者：John F. Briones、Huw M. L. Davies

  DOI：10.1021/ol201503j

  日期：2011.8.5

  Silver triflate was found to be an efficient catalyst for the cyclopropenation of internal alkynes using donor-/acceptor-substituted diazo compounds as carbenoid precursors. Highly substituted cyclopropenes, which cannot be synthesized directly via rhodium(II)-catalyzed carbenoid chemistry, can now be readily accessed.