2,3-dihydro-4-methoxy-1H-phenalen-1-one | 183237-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 2,3-dihydro-4-methoxy-1H-phenalen-1-one
• 英文别名: 4-methoxy-2,3-dihydro-1H-phenalen-1-one；4-methoxy-2,3-dihydrophenalen-1-one；4-methoxyperinaphthanone；4-methoxy-2,3-dihydro-phenalen-1-one；4-Methoxy-2,3-dihydro-phenalen-1-on；4-Methoxy-2,3-dihydro-1H-phenalenone
• CAS: 183237-41-4
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: DWOQHECCLVLWLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-4-methoxy-1H-phenalen-1-one 在 乙醚 、 碘 、 Petroleum ether 、 苯 作用下， 生成 7-(2-chloro-phenyl)-2,3-dihydro-phenalen-1-one
  参考文献：
  名称：

  379.多环芳烃。第XXXV部分。环萘系列中的异构化

  摘要：

  DOI：

  10.1039/jr9490001768
• 作为产物：
  描述：

  3-(2-Methoxy-naphthalen-1-yl)-propionyl chloride 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2,3-dihydro-4-methoxy-1H-phenalen-1-one
  参考文献：
  名称：

  Synthesis of musafluorone: a naphthoxanthenone isolated from Musa acuminata

  摘要：

  5-Methoxy-3H-naphtho[2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium bromide to 4-methoxyperinaphthenone afforded the corresponding 4-methoxy-9-phenylphenalenone which, after epoxidation and methyl transposition, was subjected to a photochemical cyclization procedure to furnish 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.128

文献信息

• Synthesis of Phenalene and Acenaphthene Derivatives as New Conformationally Restricted Ligands for Melatonin Receptors
  作者：Carole Jellimann、Monique Mathé-Allainmat、Jean Andrieux、Stéphane Kloubert、Jean A. Boutin、Jean-Paul Nicolas、Caroline Bennejean、Philippe Delagrange、Michel Langlois

  DOI：10.1021/jm000922c

  日期：2000.11.1

  Conformationally restricted phenalene and acenaphthene derivatives 5 were synthesized from phenalen-1-one and acenaphthen-1-one derivatives using the Horner-Emmons reaction. The amines were prepared through the corresponding isocyanates by the Curtius reaction on the acids or by the reduction of the nitriles. Amido derivatives (R(3) = Me, Et, n-Pr, c-Pr) were prepared by acylation of the amines with

  使用Horner-Emmons反应，从苯甲醛-1-酮和a庚啶-1-酮衍生物合成了构象受限的苯酞和衍生物5。胺是通过相应的异氰酸酯通过对酸的库尔修斯反应或通过腈的还原而制备的。酰胺衍生物（R（3）= Me，Et，n-Pr，c-Pr）是通过将胺与适当的酸酐或酰氯进行酰化或通过腈的还原酰化来制备的。使用鸡脑褪黑激素和HEK-293细胞中表达的人MT（1）和MT（2）受体，在结合测定中体外评估了化合物对褪黑素结合位点的亲和力。化合物的功能取决于减轻非洲爪蟾（Xenopus laevis）the皮肤的能力。获得了高效的化合物。数据突出显示了在获得具有皮摩尔亲和力的化合物（例如14c）时位于乙基酰胺基链邻位的甲氧基的作用（鸡脑，hMT（1），hMT（2）K（i）值= 0.02、0.008 ，分别为0.069 nM）。化合物14c与相应的二甲氧基衍生物15c等价（鸡脑，hMT（1），hMT（2）K（i）值分别为0
• N,N-dimethylacrylamide-triflic anhydride complex as a novel bifunctional electrophile in reaction with electron-rich aromatics
  作者：Valentine G. Nenajdenko、Ivan L. Baraznenok、Elizabeth S. Balenkova

  DOI：10.1016/0040-4020(96)00780-6

  日期：1996.9

  The reaction of N,N-dimethylacrylamide/trifluoromethanesulfonic anhydride complex with alkoxybenzenes followed by hydrolysis leads to the corresponding indan-1-ones and 1,3-diarylpropan-1-ones. Substituted naphthalenes yield dihydrophenalen-1-ones. Fused ring aromatics afford aromatic amines.

  N，N-二甲基丙烯酰胺/三氟甲磺酸酐络合物与烷氧基苯的反应，然后水解，得到相应的茚满-1-酮和1,3-二芳基丙烷-1-酮。取代的萘产生二氢苯并-1-酮。稠合的环芳烃提供芳族胺。
• Tricyclic compounds, preparation method and pharmaceutical compositions containing same
  申请人：Les Laboratoires Servier

  公开号：US06423870B1

  公开（公告）日：2002-07-23

  The invention concerns compounds of formula (I) in which: A forms a tricyclic system of formula A1, A2, A3 or A4; R1 represents a hydrogen atom, an alkyl, hydroxy, alkoxy or oxo group; (R2)m and (R3)m′ are such as defined in the description; n represents an integer such that 0≦n≦3; p represents an integer such as defined in the description; B represents a group (a) or (b). The invention is useful for preparing medicines.

  本发明涉及公式（I）的化合物，其中：A形成公式A1、A2、A3或A4的三环系统；R1代表氢原子、烷基、羟基、烷氧基或氧代基；（R2）m和（R3）m'如描述中所定义；n表示整数，使得0≤n≤3；p表示如描述中所定义的整数；B代表组（a）或（b）。本发明用于制备药物。
• Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds
  作者：Juliana Nanclares、Jesús Gil、Benjamı´n Rojano、Jairo Saez、Bernd Schneider、Felipe Otálvaro

  DOI：10.1016/j.tetlet.2008.04.095

  日期：2008.6

  4-Methoxy-1H-phenalen-1-one (4-methoxyperinaphthenone, 1), a subunit found in some Musa phytoalexins; and related natural products from the Haemodoraceae, was synthesized starting from 2-methoxynaphthalene in five steps and an overall yield of 36%. A Heck-Fujiwara coupling between ethyl acrylate and 1-bromonaphthalene afforded the corresponding (E)-naphthylpropanoic acid which, after hydrogenolysis, was subjected to a one-pot Friedel-Crafts acylation-DDQ dehydrogenation procedure to furnish 1. (c) 2008 Elsevier Ltd. All rights reserved.
• 613. Hydride ions in organic reactions. Part II. Preparation of phenalenium salts by the reaction of phenalenes with quinones in the presence of acids
  作者：D. H. Reid、R. G. Sutherland

  DOI：10.1039/jr9630003295

  日期：——