4-hydroxy-3-(3-oxobutyl)naphthalene-1,2-dione | 64198-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-3-(3-oxobutyl)naphthalene-1,2-dione
• 英文别名: 2-hydroxy-3-(3-oxobutyl)-1,4-naphthalenedione；2-hydroxy-3-(3-oxobutyl)naphthalene-1,4-dione；2-Hydroxy-3-(3-oxobutyl)-1,4-naphthoquinone；2-hydroxy-3-(oxobutyl)naphthalene-1,4-dione；2-Hydroxy-3-(3-oxobutyl)-1,4-naphthochinon；2-Hydroxy-(3-oxobutyl)-1,4-naphthochinon
• CAS: 64198-79-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: GKCMTPPTMYVLHO-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  430.2±45.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(3-oxobutyl)naphthalene-1,2-dione 在 magnesium 、 三乙胺 、 锌 作用下， 反应 8.25h， 生成 4-hydroxy-3-(3-hydroxy-3-methylbutyl)naphthalene-1,2-dione
  参考文献：
  名称：

  醌的研究。VIII †。迈克尔应用由2-羟基-1,4-萘醌为dihydronaphthopyrandiones的制备加合物‡

  摘要：

  从2-羟基-和2-羟基-7-甲氧基-1的迈克尔加合物开始获得二氢萘并吡喃-5,10-二酮7,13,16及其相应的二氢萘并吡喃-5,6-二酮8,14,17。 4-萘醌（1，9）。描述了使用2-羟基-3-（3-氧丁基）-1,4-萘醌（5）的羟基氢苯酚（4）的有效合成。

  DOI：

  10.1002/jhet.5570190233
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 丁烯酮 在 吡啶 作用下， 以 叔丁醇 为溶剂， 反应 12.0h， 以98%的产率得到4-hydroxy-3-(3-oxobutyl)naphthalene-1,2-dione
  参考文献：
  名称：

  Saitz, Claudio B.; Valderrama, Jaime A.; Tapia, Ricardo, Synthetic Communications, 1990, vol. 20, # 20, p. 3103 - 3114

  摘要：

  DOI：

文献信息

• Studies on quinones. XII. Cycloketalization of michael adducts from hydroxyquinones
  作者：Raúl Cassis、Ricardo Tapia、Jaime A. Valderrama

  DOI：10.1002/jhet.5570210345

  日期：1984.5

  ammonium chloride resulted in the formation of the p-quinonic cycloketals: trans- and cis-4-phenyl-2-methyl-2-methoxy-3,4-dihydro-2H-naphtho[2,3-b]pyran-5,10-dione (2a,2b). Cyclization of the Michael adducts 6, 10 and 11, which are structurally related to 1, with trimethyl orthoformate-methanol-ammonium chloride gave the corresponding p-quinonic cycloketals 7, 12 and 13. The structures of the regioisomers

  2-羟基-3-（1-苯基-3-氧丁基）-1,4-萘醌（1）与酸性甲醇或原甲酸三甲酯，甲醇和氯化铵的混合物的反应导致生成对-醌cycloketals：反式-和顺式-4-苯基-2-甲基-2-甲氧基-3,4-二氢-2 ħ -萘并[2,3- b ]吡喃-5,10-二酮（2A，2B）。迈克尔加合物环化6，10和11，其在结构上与1，与氯化原甲酸三甲酯-甲醇-铵，得到相应的p -quinonic cycloketals 7,12和13。基于化合物7的光谱性质并通过分析其质子核磁共振谱，提出了区域异构体2a和2b的结构。
• Synthesis of Siloxy-α-Lapachone Derivatives by Chemo- and Regioselective Diels-Alder Reactions of 3-Methylene-1,2,4-naphthotriones with Silyl Enol Ethers
  作者：Jian-Hua Xu、Da-Quan Peng、Yun Liu、Zhi-Feng Lu、Yong-Miao Shen

  DOI：10.1055/s-2008-1042950

  日期：2008.4

  2-hydroxy-1,4-naphthoquinone with aliphatic and aromatic aldehydes, take part in chemoselective hetero-Diels-Alder reactions with silyl enol ethers to give a series of siloxy-containing naphtho[2,3- B]pyran-5,10-dione (α-lapachone) derivatives in moderate to high yield. These reactions regio-selectively gave α-lapachone derivatives with an acetal structure. This regioselectivity can be rationalized by

  O-醌甲基化物，由 2-羟基-1,4-萘醌与脂肪族和芳香族醛的 Knoevenagel 缩合原位生成，与甲硅烷基烯醇醚参与化学选择性杂-Diels-Alder 反应，得到一系列含甲硅烷氧基的化合物萘并[2,3- B]吡喃-5,10-二酮（α-拉帕酮）衍生物，产率中等至高。这些反应区域选择性地产生具有缩醛结构的α-拉帕酮衍生物。这种区域选择性可以通过考虑邻醌甲基化物与甲硅烷基烯醇醚的前沿分子轨道相互作用来合理化，并考虑到能量上更有利的途径导致迈克尔加成中低能量的两性离子状过渡态两种反应物。
• The Synthesis of Some Naphtho[2,3-<i>b</i>]pyran-5,10-Quinones as Preliminary Models for Biological Evaluations
  作者：Robin G.F. Giles、Ivan R. Green、Victor I. Hugo、Joanne L. Ireland

  DOI：10.1080/00397919808004524

  日期：1998.12

  Abstract Naphtho[2,3-b]pyran-5,10-quinones related to the known antibiotic, erythrostominone 5, have been synthesized and demonstrate that biological activity is a function of the pyran ring as well as substituents at C-2 and C-4.

  摘要 Naphtho[2,3-b]pyran-5,10-quinones 与已知抗生素 erythrostominone 5 相关，已合成并证明其生物活性是吡喃环以及 C-2 和 C 上的取代基的函数。 -4.
• Trypanosoma cruzi: Activities of lapachol and α- and β-lapachone derivatives against epimastigote and trypomastigote forms
  作者：Cristian Salas、Ricardo A. Tapia、Karina Ciudad、Verónica Armstrong、Myriam Orellana、Ulrike Kemmerling、Jorge Ferreira、Juan Diego Maya、Antonio Morello

  DOI：10.1016/j.bmc.2007.10.038

  日期：2008.1

  Derivatives of natural quinones with biological activities, such as lapachol, alpha- and beta-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi cells. All tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity as compared with current trypanocidal drugs, nifurtimox and benznidazole. The results presented here show that the anti-T Cruzi activity of the alpha-lapachone derivatives can be increased by the replacement of the benzene ring by a pyridine moiety. Free radical production and consequently oxidative stress through redox cycling or production of electrophilic metabolites are the potential biological mechanism of action for these synthetic quinones. (c) 2007 Elsevier Ltd. All rights reserved.
• SAITZ, B. CLAUDIO;VALDERRAMA, JAIME A.;TAPIA, RICARDO, SYNTH. COMMUN., 20,(1990) N0, C. 3103-3114
  作者：SAITZ, B. CLAUDIO、VALDERRAMA, JAIME A.、TAPIA, RICARDO

  DOI：——

  日期：——