tert-butyl acenaphtho<1,2-c>pyrrole-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl acenaphtho<1,2-c>pyrrole-1-carboxylate
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: WFYGGMVCMGJYBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-acetoxymethyl-4-ethyl-3-methylpyrrole-2-carboxylate 、 tert-butyl acenaphtho<1,2-c>pyrrole-1-carboxylate 在 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  ena卟啉的多功能“ 3 +1”合成，一种新的高共轭四吡咯家族

  摘要：

  ena卟啉是一种新的具有强烈红移电子吸收光谱的卟啉，它是通过吡咯-2,5-二甲苯甲醛与并三吡喃酸的酸催化缩合而制得的。同样，通过c-退火的吡咯二醛可得到相关的opp-二萘并卟啉和带有稠合菲和环的混合卟啉体系。

  DOI：

  10.1016/0040-4039(96)00998-7
• 作为产物：
  描述：

  1-nitroacenaphthylene 、 异氰基乙酸叔丁酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以45%的产率得到tert-butyl acenaphtho<1,2-c>pyrrole-1-carboxylate
  参考文献：
  名称：

  ena卟啉的多功能“ 3 +1”合成，一种新的高共轭四吡咯家族

  摘要：

  ena卟啉是一种新的具有强烈红移电子吸收光谱的卟啉，它是通过吡咯-2,5-二甲苯甲醛与并三吡喃酸的酸催化缩合而制得的。同样，通过c-退火的吡咯二醛可得到相关的opp-二萘并卟啉和带有稠合菲和环的混合卟啉体系。

  DOI：

  10.1016/0040-4039(96)00998-7

文献信息

• Porphyrins with Exocyclic Rings. 13.¹ Synthesis and Spectroscopic Characterization of Highly Modified Porphyrin Chromophores with Fused Acenaphthylene and Benzothiadiazole Rings
  作者：Timothy D. Lash、Pushpa Chandrasekar、Augustine T. Osuma、Sun T. Chaney、John D. Spence

  DOI：10.1021/jo9815655

  日期：1998.11.1

  As part of a survey on the influence of fused aromatic rings on the porphyrin chromophore, a series of novel structures with fused acenaphthylene or benzothiadiazole rings have been synthesized. Base-catalyzed condensation of 1-nitroacenaphthylene or 4-nitrobenzothiadiazole with esters of isocyanoacetic acid afforded good yields of the annelated pyrroles 5 and 28. Cleavage of the ester moieties with KOH in refluxing ethylene glycol gave the unsubstituted heterocycles, and subsequent condensation with 2 equiv of acetoxymethylpyrroles 9 in acetic acid/ethanol produced the modified tripyrranes 12 and 31. Tripyrranes with terminal tert-butyl ester units were treated with TFA and condensed with 3,4-diethyl-2,5-pyrroledicarboxaldehyde 13 in dichloromethane to give, following oxidation with DDQ, the corresponding pi-extended porphyrins 14 and 32. Acenaphthoporphyrins 14 showed unique UV-vis spectra with a triply split Soret band region and a relatively strong band near 660 nm. Strongly red-shifted absorptions were also noted for the dications and the nickel(II), copper(II), and zinc chelates for this system. Thiadiazoloporphyrins 32 gave two broadened Soret bands, but the Q-band region was unexceptional. However, the nickel(II), copper(II), and zinc complexes all showed abnormally strong absorptions between 600 and 612 nm. Porphyrins with two antipodal fused aromatic rings were easily prepared by condensing c-annelated pyrroledialdehydes 17 with tripyrranes 12 and 31, and the spectroscopic properties of the resulting porphyrins showed that the observed ring-fusion effects were essentially additive. Porphyrins with two adjacent acenaphthylene rings were also prepared by the MacDonald "2 + 2" condensation, although this chemistrry gave poor results in the synthesis of a porphyrin with two fused benzothiadiazole rings. The spectroscopic properties of these new highly conjugated porphyrin structures show that ring fusion can profoundly modify the porphyrin chromophore.
• Synthesis of Tetraphenyltetraacenaphthoporphyrin:  A New Highly Conjugated Porphyrin System with Remarkably Red-Shifted Electronic Absorption Spectra
  作者：Timothy D. Lash、Pushpa Chandrasekar

  DOI：10.1021/ja961227q

  日期：1996.1.1