2-羟基-3-(4-甲氧基苄基)萘-1,4-二酮 | 59304-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-羟基-3-(4-甲氧基苄基)萘-1,4-二酮
• 英文名称: 2-hydroxy-3-(4-methoxybenzyl)naphthalene-1,4-dione
• 英文别名: 2-hydroxy-3-(4-methoxybenzyl)-1,4-naphthoquinone；2-Hydroxy-3-(4'-methoxybenzyl)-1,4-naphthochinon
• CAS: 59304-99-3
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: DKOJAMITDVVFPR-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  487.2±45.0 °C(predicted)
• 密度：
  1.351±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-羟基-3-(4-甲氧基苄基)萘-1,4-二酮 生成 4-hydroxy-3-(4-methoxyphenyl)naphthalene-1,2-dione
  参考文献：
  名称：

  Hewgill,F.R.; Mullings,L.R., Australian Journal of Chemistry, 1975, vol. 28, p. 355 - 367

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯甲醚 、 2-羟基-1,4-萘醌 在 二叔丁基过氧化物 作用下， 生成 2-羟基-3-(4-甲氧基苄基)萘-1,4-二酮
  参考文献：
  名称：

  Hewgill,F.R.; Mullings,L.R., Australian Journal of Chemistry, 1975, vol. 28, p. 355 - 367

  摘要：

  DOI：

文献信息

• A New Method to Prepare 3-Alkyl-2-hydroxy-1,4-naphthoquinones: [nl]Synthesis of Lapachol and Phthiocol
  作者：[nl]Vitor Ferreira、Sabrina Ferreira、David Rodrigues da Rocha、José Carneiro、Wilson Santos

  DOI：10.1055/s-0030-1260771

  日期：2011.7

  In this article a mild, simple, safe, and chemoselective synthesis and reduction of o-quinone methides to the corresponding 3-alkyl-2-hydroxy-1,4-naphthoquinones, compounds with interesting biological activity, mediated by the formic acid-water system is described. This new one-pot methodology was applied to the synthesis of lapachol and constitutes an efficient and inexpensive alternative for the preparation of this natural bioactive compound

  本文介绍了一种温和、简单、安全且化学选择性强的合成与还原邻醌甲烷为相应的3-烷基-2-羟基-1,4-萘醌的方法，这些化合物具有有趣的生物活性，通过甲酸-水体系介导。这种新的一锅法方法应用于合成拉帕醇，为制备这种天然生物活性化合物提供了一种高效且经济的替代方案。
• Organocatalytic Enantioselective Michael‐Aldol[3+2] Annulation for the Synthesis of Nitro‐Methanobenzo[7] annulenes
  作者：Yang Zhang、Jin‐Yu Liu、Xiao‐Hai Zhang

  DOI：10.1002/ejoc.202100974

  日期：2021.9.21

  An enantioselective Michael-Aldol[3+2] annulation via bifunctional thiourea catalysis has been reported, and a series of nitro-methanobenzo[7]annulenes with potential biological activities were synthesized in good yields with excellent enantio- and diastereoselectivities.

  已经报道了通过双功能硫脲催化的对映选择性 Michael-Aldol[3+2] 环化，并以良好的收率合成了一系列具有潜在生物活性的硝基甲烷苯并 [7] 环烯，并具有优异的对映选择性和非对映选择性。
• Organocatalytic Asymmetric Formal [3+2] Cycloaddition as a Versatile Platform to Access Methanobenzo[7]annulenes
  作者：Dhevalapally B. Ramachary、Mohammed Anif Pasha、Guguloth Thirupathi

  DOI：10.1002/anie.201706557

  日期：2017.10.9

  and structurally important methanobenzo[7]annulenes were synthesized in very good yields with excellent enantio‐ and diastereoselectivities through an unprecedented organocatalytic formal [3+2] cycloaddition from readily available 2‐alkyl‐3‐hydroxynaphthalene‐1,4‐diones and alkyl vinyl ketones.

  药学上和结构上重要的甲氧基苯并[7]环戊烯可通过空前的2-烷基-3-羟基萘-1,4-二酮和烷基的空前的有机催化形式[3 + 2]环加成反应以良好的对映异构和非对映选择性很好地合成。乙烯基酮。
• Stereoselective Insertion of Benzynes into Lawsones: Synthesis of Biologically Important Benzannulated Bicyclo[3.3.0]octanes
  作者：A. Suresh Kumar、Guguloth Thirupathi、G. Surendra Reddy、Dhevalapally B. Ramachary

  DOI：10.1002/chem.201805798

  日期：2019.1.24

  stereoselective insertion of in situ generated benzynes into lawsones through domino formal [2+2]‐cycloaddition followed by rearrangement is disclosed. The reaction allowed for the preparation of biologically important benzannulated bicyclo[3.3.0]octanes in good yields and with excellent selectivities by using simple substrates and conditions.

  公开了通过多米诺形式[2 + 2]-环加成反应然后原位重排的方法，将原位生成的苯炔类化合物理想地立体选择性地插入到法拉酮中。通过使用简单的底物和条件，该反应允许以良好的产率和优异的选择性制备生物学上重要的苯并双环[3.3.0]辛烷。
• Phosphine-Catalyzed [3 + 2] Annulation of 2-Hydroxy-1,4-naphthaquinones and Allenoate: An Allene–Alkene [3 + 2] Annulation Mechanism Involving Consecutive γ-Addition–Aldol Reaction
  作者：Leijie Zhou、Chang Wang、Chunhao Yuan、Honglei Liu、Cheng Zhang、Hongchao Guo

  DOI：10.1021/acs.orglett.8b02947

  日期：2018.10.19

  achieved via a phosphine-catalyzed [3 + 2] annulation of 2-hydroxy-1,4-naphthaquinone derivatives and allenoate. Various tetrahydrocyclopenta[b]naphthalene derivatives containing contiguous quaternary carbon centers are obtained in good yields with excellent diastereoselectivities. The asymmetric version gave the chiral product in up to 57% ee under catalysis of Kwon chiral phosphine. The reaction undergoes

  通过膦催化的2-羟基-1,4-萘醌衍生物和脲基甲酸酯的[3 + 2]环构反应，已实现了对生物重要的四氢环戊五烯[ b ]萘衍生物的非对映选择性。获得具有连续的季碳中心的各种四氢环戊并[ b ]萘衍生物，具有良好的收率和极好的非对映选择性。在Kwon手性膦的催化下，不对称形式使手性产物的收率高达57％ee。该反应经历的反应机理包括连续的γ加成-醛醇缩合反应。