2,5-bis(4-propyl-2-pyrrolyl)thiophene | 142038-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-bis(4-propyl-2-pyrrolyl)thiophene
• 英文别名: 4-propyl-2-[5-(4-propyl-1H-pyrrol-2-yl)thiophen-2-yl]-1H-pyrrole
• CAS: 142038-36-6
• 化学式: C₁₈H₂₂N₂S
• 分子量: 298.452
• InChiKey: CPWKPRCGLVHCMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-propyl-2-pyrrolyl)thiophene 在 吡啶 、 air 、 四氯化钛 、 苯甲酰氯 、 锌 作用下， 反应 28.0h， 生成 bronzaphyrin SS
  参考文献：
  名称：

  Synthesis and characterization of a new 26.pi.-aromatic thiophene-containing macrocyclic ligand

  摘要：

  A new porphyrin-like or ''pentaplanar'' macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and H-1 NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

  DOI：

  10.1021/jo00042a019
• 作为产物：
  描述：

  240.0 ℃ 、13.33 Pa 条件下， 生成 2,5-bis(4-propyl-2-pyrrolyl)thiophene
  参考文献：
  名称：

  Synthesis and characterization of a new 26.pi.-aromatic thiophene-containing macrocyclic ligand

  摘要：

  A new porphyrin-like or ''pentaplanar'' macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and H-1 NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

  DOI：

  10.1021/jo00042a019

文献信息

• Synthesis and Antiaromatic Properties of Highly Planar Dithiaamethyrin
  作者：Yoshihiro Ishimaru、Naoyuki Shimoyama、Takashi Fujihara、Keigo Watanabe、Jun-ichiro Setsune

  DOI：10.1002/asia.201403126

  日期：2015.2

  to afford large porphyrinoids; [24]dithiaamethyrin(1.0.0.1.0.0) and [36]trithianonaphyrin(1.0.0.1.0.0.1.0.0). X‐ray crystallography of the dithiaamethyrin revealed a highly planar ring structure with mean plane deviation (MPD) value of 0.053 Å. A large positive NICS(0) value (+13.9 ppm) calculated for this planar 24π system unambiguously indicates an antiaromatic character that is consistent with a

  2,5-双（4-丙基-2-吡咯基）噻吩与芳基醛反应生成大卟啉类化合物; [24]二硫氨甲腺苷（1.0.0.1.0.0）和[36]三噻吩甲酸酯（1.0.0.1.0.0.1.0.0）。二硫氨甲菊酯的X射线晶体学分析显示高度平坦的环结构，平均平面偏差（MPD）值为0.053Å。针对该平面24π系统计算出的大NICS（0）正值（+13.9 ppm）明确表示抗芳烃特性与极低的场1一致内部NH质子的H化学位移为24.0 ppm。基于MPD值和NICS值，讨论了游离碱形式和双质子化形式的24π甲基丙烯酸盐溶液中的顺性环电流效应的大小。本发明的二硫杂菊酯以其游离碱形式比十二烷基甲硫氨酸具有更强的抗芳香性，但其双质子化形式的顺序相反。
• <i>Syn</i> and <i>Anti</i> Metal Complexes of 24π Antiaromatic Bis(Dicarbonylrhodium(I))Dithiaamethyrin
  作者：Yoshihiro Ishimaru、Fumiya Takahashi、Samu Mochizuki、Natsuki Hosoda、Takashi Fujihara

  DOI：10.1002/asia.202200198

  日期：2022.7.15

  anti bis(dicarbonylrhodium(I)) complexes 6 were simultaneously isolated as quite stable isomers from the reaction of tetrapropyl[24]dithiaamethyrin(1.0.0.1.0.0) (an antiaromatic 24π system) with [Rh(CO)2Cl]2. X-ray structural analyses revealed that 6-anti is more planar than 6-syn, while 1H NMR spectroscopy suggests that 6-anti possesses stronger paratropic ring current.

  从四丙基[24]二硫甲氰菊酯(1.0.0.1.0.0)（一种反芳族24π体系）与[Rh(CO) 2 Cl]的反应中同时分离出顺式和 反 式双(二羰基铑(I ))配合物6作为相当稳定的异构体2 . X射线结构分析表明6 - anti比6 - syn更平面，而1 H NMR光谱表明6 - anti具有更强的顺向环电流。