4-hydroxy-3-(3-hydroxy-3-methylbutyl)naphthalene-1,2-dione | 15298-01-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-hydroxy-3-(3-hydroxy-3-methylbutyl)naphthalene-1,2-dione
• 英文别名: 2-hydroxy-3-(3-hydroxy-3-methylbutyl)-naphthalene-1,4dione；2-hydroxy-3-(3-hydroxy-3-methylbutyl)-1,4-naphthoquinone；Hydroxyhyrdrolapachol；2-hydroxy-3-(3-hydroxy-3-methyl-butyl)-[1,4]naphthoquinone；2-Hydroxy-3-(3-hydroxy-3-methyl-butyl)-[1,4]naphthochinon；2-Hydroxy-3-(3-hydroxy-3-methyl-butyl)-1.4-naphthochinon；γ-Hydroxyhydrolapachol
• CAS: 15298-01-8
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: OVRABUAZHGSQBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(3-hydroxy-3-methylbutyl)naphthalene-1,2-dione 在 碘 、 三乙胺 、 锌 作用下， 以 xylene 为溶剂， 生成 1,2,4-三乙酰氧基-3-(3-甲基-丁-2-烯基)-萘
  参考文献：
  名称：

  Lapachol

  摘要：

  一种实用的羟基羟基拉帕醇和拉帕醇的全合成已经总结出来。

  DOI：

  10.1139/v68-404
• 作为产物：
  描述：

  ALPHA-拉杷醌 在 氢氧化钾 、 硫酸 、 水 作用下， 生成 4-hydroxy-3-(3-hydroxy-3-methylbutyl)naphthalene-1,2-dione
  参考文献：
  名称：

  Hooker, Journal of the Chemical Society, 1892, vol. 61, p. 638

  摘要：

  DOI：

文献信息

• Synthesis of hydroxyhydrolapachol and lapachol
  作者：George R. Pettit、Leonard E. Houghton

  DOI：10.1039/j39710000509

  日期：——

  hydroxyhydrolapachol (IIa) and lapachol (I) are reported. Treatment of 2-hydroxy-1,4-naphthoquinone with succinyl peroxide gave the carboxyethyl compound (IVa) which was esterified to give the ethyl ester (IVb). Reductive acetylation of this gave a triacetate (VI) which upon treatment with methylmagnesium iodide, and oxidation of the resulting product, gave hydroxyhydrolapachol. Repeating the reductive acetylation step

  据报道，羟基氢lapachol（IIa）和lapachol（I）的合成很方便。用过氧化琥珀酰处理2-羟基-1，4-萘醌，得到羧乙基化合物（IVa），其被酯化得到乙酯（IVb）。对其进行还原性乙酰化，得到三乙酸酯（VI），将其用甲基碘化镁处理，并将所得的产物氧化，得到羟基氢萘酚。重复用羟基氢lapachol进行还原性乙酰化步骤，然后在二甲苯中用碘处理并进行皂化反应，产生了lapachol。
• Studies on quinones. VIII. The application of michael adducts from 2-hydroxy-1,4-naphthoquinones for the preparation of dihydronaphthopyrandiones
  作者：R. Cassis、R. Tapia、J. Valderrama

  DOI：10.1002/jhet.5570190233

  日期：1982.3

  Dihydronaphthopyran-5,10-diones 7,13, 16 and their corresponding dihydronaphthopyran-5,6-diones 8, 14,17 have been obtained starting from Michael adducts of 2-hydroxy- and 2-hydroxy-7-methoxy-1,4-naph-thoquinone (1, 9). An efficient synthesis of hydroxyhydrolapachol (4) employing 2-hydroxy-3-(3-oxobutyl)-1,4-naphthoquinone (5) is described.

  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。
• Light effect on the stability of <i>β</i>-lapachone in solution: pathways and kinetics of degradation
  作者：Marcílio S S Cunha-Filho、Ana Estévez-Braun、Elisa Pérez-Sacau、Ma Magdalena Echezarreta-López、Ramón Martínez-Pacheco、Mariana Landín

  DOI：10.1111/j.2042-7158.2011.01323.x

  日期：2011.8.9

  The purpose of this work was to study the chemical stability of the new antitumoral β-lapachone (βLAP) to determine the degradation pathway/s of the molecule and the degradation kinetics in addition to identifying several degradation products.

  Method  Samples of βLAP in solution were stored under conditions of darkness and illumination at 40°C at which the pseudo-first order rate constants for the βLAP degradation were determined. Furthermore, drug degraded solutions were concentrated and purified using Sephadex LH-20 and preparative thin-layer chromatography and degradation products were identified by nuclear magnetic resonance spectroscopy.

  The results revealed that βLAP shows two different degradation routes: hydrolysis in the dark and photolysis under the light. The βLAP exposure to light accelerated the drug degradation about 140 fold, compared with the samples stored in the absence of light. The hydrolysis produced hydroxylapachol as the main degradation product. The photolysis yielded phthalic acid, 6-hydroxy-3methylene-3H-isobenzofuran-1-one and a benzomacrolactone together with a complex mixture of other phthalate-derivatives such as 2-(2-carboxy-acetyl)-benzoic acid.

  This study provides useful information for the development of βLAP dosage forms, their storage, manipulation and quality control.

  本研究旨在研究新型抗肿瘤药物β-拉帕霉素（βLAP）的化学稳定性，确定分子的降解途径和降解动力学，并鉴定多种降解产物。

  方法：βLAP溶液样品在40°C的黑暗和照明条件下储存，测定βLAP降解的伪一阶速率常数。此外，使用Sephadex LH-20和制备性薄层色谱对药物降解溶液进行浓缩和纯化，并使用核磁共振光谱鉴定降解产物。

  结果显示，βLAP有两种不同的降解途径：在黑暗中水解，在光照下光解。与不受光照的样品相比，βLAP暴露于光线下加速了药物降解约140倍。水解产生羟基拉帕醌作为主要降解产物。光解产生邻苯二甲酸、6-羟基-3-亚甲基-3H-异苯并呋喃-1-酮和苯并马克酸内酯以及其他邻苯二甲酸衍生物的复杂混合物，如2-（2-羧乙酰基）苯甲酸。

  本研究为βLAP剂型的开发、储存、操作和质量控制提供了有用的信息。

• Fieser, Journal of the American Chemical Society, 1948, vol. 70, p. 3237,3240
  作者：Fieser

  DOI：——

  日期：——
• CASSIS, R.;TAPIA, R.;VALDERRAMA, J., J. HETEROCYCL. CHEM., 1982, 19, N 2, 381-384
  作者：CASSIS, R.、TAPIA, R.、VALDERRAMA, J.

  DOI：——

  日期：——