1-benzyl-2-((3-methoxyphenyl)ethynyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-benzyl-2-((3-methoxyphenyl)ethynyl)-1H-pyrrole
• 英文别名: 1-Benzyl-2-[2-(3-methoxyphenyl)ethynyl]pyrrole；1-benzyl-2-[2-(3-methoxyphenyl)ethynyl]pyrrole
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: ABPNWZQSUCLVOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-乙炔基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 sodium acetate 、 palladium diacetate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 13.0h， 生成 1-benzyl-2-((3-methoxyphenyl)ethynyl)-1H-pyrrole
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Alkynylation of Pyrroles and Azoles under Mild Conditions: Application to the Synthesis of a Dopamine D-4 Receptor Agonist

  摘要：

  A mild and general method for the direct alkynylation of azoles such as pyrrole, indole, and 7-azaindole is described here. Using a simple catalytic system such as Pd(OAc)(2) (2.5 mol %), P(tBu)(2)Me center dot HBF4 (5 mol %), and NaOAc (2 equiv) allowed the regioselective introduction of various alkynyl residues at the C-2 position of pyrroles. Interestingly, C-2 alkynylation was also observed on C-3-substituted indoles, whereas classical C-3 alkynylation was obtained on selected unsubstituted indoles and 7-azaindole. Our methodology has been illustrated by the efficient synthesis of a potential schizophrenia drug (dopamine D-4 inhibitor).

  DOI：

  10.1021/acs.joc.5b01093

文献信息

• Palladium-Catalyzed Regioselective Alkynylation of Pyrroles and Azoles under Mild Conditions: Application to the Synthesis of a Dopamine D-4 Receptor Agonist
  作者：Etienne Brachet、Philippe Belmont

  DOI：10.1021/acs.joc.5b01093

  日期：2015.8.7

  A mild and general method for the direct alkynylation of azoles such as pyrrole, indole, and 7-azaindole is described here. Using a simple catalytic system such as Pd(OAc)(2) (2.5 mol %), P(tBu)(2)Me center dot HBF4 (5 mol %), and NaOAc (2 equiv) allowed the regioselective introduction of various alkynyl residues at the C-2 position of pyrroles. Interestingly, C-2 alkynylation was also observed on C-3-substituted indoles, whereas classical C-3 alkynylation was obtained on selected unsubstituted indoles and 7-azaindole. Our methodology has been illustrated by the efficient synthesis of a potential schizophrenia drug (dopamine D-4 inhibitor).