2-bromo-1H-phenalen-1-one | 3352-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 2-bromo-1H-phenalen-1-one
• 英文别名: 2-bromo-1-phenalenone；2-bromophenalenone；2-bromo-phenalen-1-one；2-Brom-phenalen-1-on；2-Brom-perinaphthindon；2-Brom-perinaphthenon；2-bromophenalen-1-one
• CAS: 3352-83-8
• 化学式: C₁₃H₇BrO
• 分子量: 259.102
• InChiKey: ZGECPZHXUNAVFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• 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-bromo-1H-phenalen-1-one 在 盐酸 作用下， 生成 2-cyclohexylamino-phenalen-1-one
  参考文献：
  名称：

  Endocyclic α,β-Unsaturated Ketones. III.¹ Reaction of 2-Bromo-4,4-dimethyl-1-keto-1,4-dihydronaphthalene with Amines²

  摘要：

  DOI：

  10.1021/ja01147a105
• 作为产物：
  描述：

  2-aminophenalenone 在 copper(I) bromide 、 硫酸 、 氢溴酸 、 sodium nitrite 作用下， 生成 2-bromo-1H-phenalen-1-one
  参考文献：
  名称：

  Solodar', S. L.; Kochkin, V. A., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1809 - 1812

  摘要：

  DOI：

文献信息

• 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。
• Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
  作者：Mónica Blanco Freijo、Atteneri López-Arencibia、José E. Piñero、Grant McNaughton-Smith、Teresa Abad-Grillo

  DOI：10.1016/j.ejmech.2017.10.032

  日期：2018.1

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.
• DE677967
  申请人：——

  公开号：——

  公开（公告）日：——
• Halogenated peri-naphthindenones
  申请人：GEN ANILINE WORKS INC

  公开号：US02145051A1

  公开（公告）日：1939-01-24
• Reactions of Perinaphthane Derivatives
  作者：Louis F. Fieser、Lawrence W. Newton

  DOI：10.1021/ja01256a051

  日期：1942.4