4,9-dihydro-4,9-ethano-2H-benz[f]isoindole | 287378-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,9-dihydro-4,9-ethano-2H-benz[f]isoindole
• 英文别名: 11-Azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9,12-pentaene
• CAS: 287378-38-5
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: UOHWTFGDLWOJNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4,9-dihydro-4,9-ethano-2H-benz[f]isoindole 、 2,5-bis(3-n-butyl-5-formyl-4-methyl-2-pyrrolylmethyl)-3,4-diethyl-1-H-pyrrole 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以38%的产率得到8,17-Dibutyl-12,13-diethyl-7,18-dimethyl-2¹,2⁶-dihydro-2¹,2⁶-ethanonaphtho[2,3-b]porphyrinato zinc
  参考文献：
  名称：

  SYNTHESIS OF BIS-nAPHTHOPORPHYRINS

  摘要：

  Ethanonaphthoporphyrins with a halogen atom at the zeta position were prepared by the [3+1] porphyrin synthesis of halogen-substituted ethanobenz[f]isoindole with a tripyrrane derivative. The halogeno porphyrins were converted to the corresponding ethynyl and pinacolatoboronyl compounds by Sonogashira and borylation reactions, respectively. Suzuki, Sonogashira, and Glaser coupling reactions of these ethanonaphthoporphyrins gave bis-porphyrins connected with no atom, acetylene, and butadiyne, respectively. Retro Diels-Alder reaction of these bis-porphyrins brought about the conversion of bicyclo[2.2.2]octadiene (BCOD) to benzene moieties to give bis-naphthoporphyrins, quantitatively.

  DOI：

  10.3987/com-12-s(n)50
• 作为产物：
  描述：

  2-chloro-3-phenyltho-1,4-dihydro-1,4-ethanonaphthalene 在 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二醇 为溶剂， 反应 13.0h， 生成 4,9-dihydro-4,9-ethano-2H-benz[f]isoindole
  参考文献：
  名称：

  SYNTHESIS OF BIS-nAPHTHOPORPHYRINS

  摘要：

  Ethanonaphthoporphyrins with a halogen atom at the zeta position were prepared by the [3+1] porphyrin synthesis of halogen-substituted ethanobenz[f]isoindole with a tripyrrane derivative. The halogeno porphyrins were converted to the corresponding ethynyl and pinacolatoboronyl compounds by Sonogashira and borylation reactions, respectively. Suzuki, Sonogashira, and Glaser coupling reactions of these ethanonaphthoporphyrins gave bis-porphyrins connected with no atom, acetylene, and butadiyne, respectively. Retro Diels-Alder reaction of these bis-porphyrins brought about the conversion of bicyclo[2.2.2]octadiene (BCOD) to benzene moieties to give bis-naphthoporphyrins, quantitatively.

  DOI：

  10.3987/com-12-s(n)50

文献信息

• The Synthesis and Properties of Free‐Base [14]Triphyrin(2.1.1) Compounds and the Formation of Subporphyrinoid Metal Complexes
  作者：Zhao Li Xue、John Mack、Hua Lu、Lei Zhang、Xiao Zeng You、Daiki Kuzuhara、Martin Stillman、Hiroko Yamada、Seigo Yamauchi、Nagao Kobayashi、Zhen Shen

  DOI：10.1002/chem.201003100

  日期：2011.4.11

  diethylpyrrole (1 a) and fused pyrroles of bicyclo[2.2.2]octadiene (BCOD) (2 a–e) and dihydroethanonaphthalene (4 a) with various aryl aldehydes. The concentration of BF3⋅OEt2 catalyst plays the key role in determining the yield of the [14]triphyrin(2.1.1) macrocycle relative to the conventional tetrapyrrole porphyrin product. Retro‐Diels–Alder reactions of 2 a–e and 4 a result in the formation of

  描述了[14] triphyrin（2.1.1）化合物的合成。与通常包含中心硼原子的常规亚卟啉相反，可以形成游离碱杂芳族化合物。基于二乙基吡咯（1a）与双环[2.2.2]辛二烯的稠合吡咯的反应，使用改良的Lindsey方法制备了一系列不同的[14]三卟啉（2.1.1），收率最高为35％。BCOD）（2 a – e）和二氢乙烷萘（4 a）与各种芳基醛。BF的浓度3 ⋅OEt 2相对于常规四吡咯卟啉产物，催化剂在确定[14] triphyrin（2.1.1）大环化合物的产率中起关键作用。2 a – e和4 a的Retro-Diels–Alder反应导致形成[14]三苯并三卟啉（2.1.1）（3 a – e）和[14]三萘并卟啉（2.1.1）（5 a）。基于光谱学，理论计算和电化学测量，详细研究了环外环空对电子结构的影响。游离碱化合物的存在使[Re I（CO）3（triphyrin）]（6 a）和[Ru
• Molecular Engineering of Corrole Radicals by Polycyclic Aromatic Fusion: Towards Open‐Shell Near‐Infrared Materials for Efficient Photothermal Therapy
  作者：Hu Gao、Xu Zhi、Fan Wu、Yue Zhao、Fangjian Cai、Pengfei Li、Zhen Shen

  DOI：10.1002/anie.202309208

  日期：2023.10.2

  radicals and their cations exhibiting superior absorbing capacities across the visible-to-near-infrared (NIR) spectral region are synthesized via the radial fusion of aromatic rings. The nanoparticles encapsulating corrole radicals are high-performance photothermal agents and enable efficient NIR-triggered photoacoustic imaging and photothermal therapy in vivo.

  通过芳环的径向融合合成了高度稳定的 π 延伸镍咯咯自由基及其阳离子，在可见光到近红外 (NIR) 光谱区域表现出优异的吸收能力。封装咔咯自由基的纳米颗粒是高性能光热剂，可实现有效的近红外触发光声成像和体内光热治疗。
• Copper naphthoporphyrin showing enhanced water-solubility by nano-encapsulation and efficient photoacoustic response
  作者：Yufen Sun、Fan Wu、Hu Gao、Xu Zhi、Yue Zhao、Zhen Shen

  DOI：10.1080/10610278.2023.2175678

  日期：2021.12.2