2-phenyl-1H-phenalen-1-one | 73873-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-1H-phenalen-1-one
• 英文别名: 2-phenylphenalenone；fuliginone；2-phenyl-phenalen-1-one；1-Oxo-2-phenyl-perinaphthinden；2-Phenyl-perinaphthindenon-(1)；2-Phenyl-phenalen-1-on；2-phenylphenalen-1-one
• CAS: 73873-15-1
• 化学式: C₁₉H₁₂O
• 分子量: 256.304
• InChiKey: XLKSZOCYJIRNJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-1H-phenalen-1-one 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以90 %的产率得到2-phenyl-1H-phenalene
  参考文献：
  名称：

  π‐Radical Cascade to a Chiral Saddle‐Shaped Peropyrene

  摘要：

  Reactions of open‐shell molecular graphene fragments are typically thought of as undesired decomposition processes because they lead to the loss of desired features like π‐magnetism. Oxidative dimerization of phenalenyl to peropyrene shows, however, that these transformations hold promise as a synthetic tool for making complex structures via formation of multiple bonds and rings in a single step. Here, we explore the feasibility of using this “undesired” reaction of phenalenyl to build up strain and provide access to non‐planar polycyclic aromatic hydrocarbons. To this end, we designed and synthesized a biradical system with two phenalenyl units linked via a biphenylene backbone. The design facilitates an intramolecular cascade reaction to a helically twisted saddle‐shaped product, where the key transformations—ring‐closure and ring‐fusion—occur within one reaction. The negative curvature of the final peropyrene product, induced by the formed eight‐membered ring, was confirmed by single‐crystal X‐ray diffraction analysis and the helical twist was validated via resolution of the product's enantiomers that display circularly polarized luminescence and high configurational stability.

  DOI：

  10.1002/anie.202318254
• 作为产物：
  描述：

  (E)-8-Styryl-1-naphthoic acid 在 PPA 作用下， 反应 3.5h， 生成 2-phenyl-1H-phenalen-1-one
  参考文献：
  名称：

  Intramolecular Friedel-Crafts acylation of a lactone in polyphosphoric acid. Synthesis of 2-phenylphenalen-1-one

  摘要：

  DOI：

  10.1021/jo01304a050

文献信息

• Gold(I)-Catalyzed Formation of Naphthalene/Acenaphthene Heterocyclic Acetals
  作者：Malina Michalska、Krzysztof Grudzień、Paweł Małecki、Karol Grela

  DOI：10.1021/acs.orglett.7b03856

  日期：2018.2.16

  developed. All reactions, performed in mild conditions, exhibited high regioselectivity and good to excellent reaction yields. Additionally, optimized methodology was used in total synthesis of 2-phenylphenalenone, an alleged natural product found in Macropidia fuliginosa plant.

  开发了金催化的加成/环化反应以形成3-烷氧基-苯并[de]异戊烯衍生物。在温和条件下进行的所有反应均表现出高区域选择性和良好至极好的反应产率。另外，优化的方法被用于2-苯基苯丙烯酮的全合成，2-苯基苯丙烯酮是在大叶卷叶蝉植物中发现的一种所谓的天然产物。
• Synthesis of Positional Isomeric Phenylphenalenones
  作者：Felipe Ospina、Adrian Ramirez、Marisol Cano、William Hidalgo、Bernd Schneider、Felipe Otálvaro

  DOI：10.1021/acs.joc.6b02985

  日期：2017.4.7

  A series of isomeric phenylphenalenones in which the phenyl ring is located at all possible peripheral positions of the phenalenone nuclei was synthesized. The structural characteristics of the series, in which topological variation is permitted with minimal electronic disturbance, could, in principle, allow for easy pharmacophore recognition when the compounds are aligned in steroidomimetic conformations

  合成了一系列异构体苯基苯乙酮，其中苯环位于菲拉烯酮核的所有可能的周边位置。该系列的结构特征允许在最小的电子干扰的情况下进行拓扑变化，原则上，当这些化合物以类固醇构象排列时，可以轻松地实现药效基团的识别。
• One‐Pot Construction of Sulfonyl Benzonorcaradienes
  作者：Meng‐Yang Chang、Chun‐Yi Lin

  DOI：10.1002/adsc.202300012

  日期：2023.3.21

  We report here on a one-pot stereoselective synthesis of strained sulfonyl benzonorcaradienes, which proceeds through base-mediated tandem annulation of o-bis-sulfonylmethyl arenes with diversified chalcones (α,β-unsaturated carbonyls) via intermolecular desulfonylative cyclopropanation, followed by intramolecular condensation. A plausible mechanism is proposed and discussed. The proposed synthetic

  我们在这里报告了应变磺酰基苯并碳二烯的一锅法立体选择性合成，它通过碱介导的o -双磺酰甲基芳烃与多种查耳酮（α,β-不饱和羰基）的串联环化通过分子间脱磺酰化环丙烷化反应进行，然后进行分子内缩合. 提出并讨论了一种合理的机制。拟议的合成路线形成两个碳-碳单 (CC) 键和一个碳-碳双 (C=C) 键。
• Polyarylene oxide and method of producing the same
  申请人：Higashimura Hideyuki

  公开号：US20050096452A1

  公开（公告）日：2005-05-05

  A method of producing a polyarylene oxide comprising a step of oxidative polymerization of a monomer represented by the general formula (1) in an organic solvent in the presence of a transition metal compound, wherein, Ar represents a benzene ring or a naphthalene ring, R 1 represents a hydrocarbon group optionally substituted, a hydrocarbonoxy group optionally substituted, or a halogen atom; a represents an integer of 0 to 5, and when a is 2 or more, R 1 s may be the same or different, adjacent R 1 s may mutually bond to form a ring; R 2 represents a single bond or an arylene group; R 3 represents a hydrocarbon group optionally substituted or a trialkylsilyl group.

  一种生产聚芳醚的方法，包括通式(1)所代表的单体在有机溶剂中在过渡金属化合物存在下进行氧化聚合的步骤、 其中 Ar 代表苯环或萘环，R 1 代表任选取代的烃基、任选取代的烃氧基或卤原子；a 代表 0 至 5 的整数，当 a 为 2 或 2 以上时，R 1 s 可以相同或不同，相邻的 R 1 可相互结合形成一个环；R 2 代表单键或芳基；R 3 代表任选取代的烃基或三烷基硅烷基。
• DE384982
  申请人：——

  公开号：——

  公开（公告）日：——