5,8-二羟基-2,7-二甲氧基萘-1,4-二酮 | 2808-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5,8-二羟基-2,7-二甲氧基萘-1,4-二酮
• 英文名称: 5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone
• 英文别名: mompain dimethyl ether；5,8-Dihydroxy-2,7-dimethoxy-<1,4>naphthochinon；5,8-Dihydroxy-2,7-dimethoxy-1,4-naphthochinon；5,8-Dihydroxy-2,7-dimethoxy-naphthochinon-1,4；2,7-Dimethoxy-naphthazarin；Mompain-2,7-dimethylaether；5,8-dihydroxy-2,7-dimethoxynaphthalene-1,4-dione
• CAS: 2808-46-0
• 化学式: C₁₂H₁₀O₆
• 分子量: 250.208
• InChiKey: OKTQTRCTZAALBF-UHFFFAOYSA-N

物化性质

• 熔点：
  235-236 °C
• 沸点：
  579.7±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,8-二羟基-2,7-二甲氧基萘-1,4-二酮 在 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 2,5,8-trihydroxy-7-methoxy-6-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  摘要：

  A set of substituted 2-hydroxy-6(7)-methoxynaphthazarins and 7(8)-hydroxypyranonaphthazarins were synthesized. The IR spectra of 2-hydroxy-6-methoxynaphthazarins and 7-hydroxypyranonaphthazarins, on the one hand, and of 2-hydroxy-7-methoxynaphthazarins and 8-hydroxypyranonaphthazarins, on the other hand, have the characteristic nonoverlapping intervals of stretching vibration frequencies of the beta -hydroxy groups. These regularities confirm the structures of cristazarin and 6-methylcristazarin, which are metabolites of lichen Cladonia cristatella.

  DOI：

  10.1023/a:1009533403588
• 作为产物：
  描述：

  5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone 在 双氧水 、 三氟乙酸酐 作用下， 生成 5,8-二羟基-2,7-二甲氧基萘-1,4-二酮
  参考文献：
  名称：

  某些天然存在的羟基萘醌的便捷途径

  摘要：

  DOI：

  10.1039/c19680000071

文献信息

• Direct amination of naphthopurpurin and mompain, sea urchin pigments, and their O-methyl ethers by the reaction with ammonia
  作者：O. P. Shestak、V. L. Novikov、V. P. Glazunov

  DOI：10.1007/s11172-021-3152-0

  日期：2021.4

  The regiochemistry of direct amination of 2-hydroxynaphthazarin (naphthopurpurin) and 2,7-dihydroxynaphthazarin (mompain), sea urchin pigments, and their O-methyl ethers by the action of ammonia solutions in H2O and MeOH under mild conditions was studied. The predominant direction of the reactions of all substrates with NH3 was the 1,2-addition of the nucleophile to the C-O group at position 1 of the

  研究了在温和条件下，通过氨水在H 2 O和MeOH中的作用，对2-羟基萘他嘌呤（naphthopurin）和2,7-二羟基萘他莫潘（mompain），海胆颜料及其O-甲基醚进行直接胺化的区域化学。用NH所有底物的反应的主要方向3是1,2-加成的亲核试剂到CO组中的醌型环的1位的H随后消除2从α-羟胺中间体O。所得的奎宁胺进一步转化为具有NH 2基团的更稳定的互变异构体。除萘嘌呤外，所有底物均可添加两个NH 3分子形成不同的产物。讨论了所有底物与NH 3的反应机理，以及起始底物和反应产物的质子互变异构问题。
• Trimethyl orthoacetate as a convenient reagent for selective methylation of β-OH groups of (poly)hydroxynaphthazarins
  作者：N. N. Balaneva、O. P. Shestak、V. L. Novikov

  DOI：10.1007/s11172-019-2415-5

  日期：2019.1

  Trimethyl orthoacetate was found to be a convenient reagent for methylation of the β-OH groups of (poly)hydroxynaphthazarins. The substrates bearing one β-OH group react with MeC(OMe)3 to give the corresponding methoxy derivatives in 79–89% yields. Depending on the reaction conditions, methylation of substrates with two β-OH groups on the different and the same rings affords either the corresponding

  原乙酸三甲酯被发现是一种方便的试剂，用于甲基化（聚）羟基萘二甲素的 β-OH 基团。带有一个 β-OH 基团的底物与 MeC(OMe)3 反应以 79-89% 的产率得到相应的甲氧基衍生物。根据反应条件，在不同和相同的环上具有两个 β-OH 基团的底物的甲基化提供相应的单-O-甲基化（43-70%）或二-O-甲基化（71-78%）衍生物。在 O-甲基化（聚）羟基萘甲素衍生物的制备合成中，原乙酸三甲酯是 CH2N2 的良好替代品。
• The Structures of Mompain and Deoxyhelicobasidin and the Biosynthesis of Helicobasidin, Quinonoid Metabolites of Helicobasidium mompa TANAKA
  作者：Shinsaku Natori、Yuko Inouye、Hidejiro Nishikawa

  DOI：10.1248/cpb.15.380

  日期：——

  The structure of mompain, a metabolite of Helicobasidium mompa, was established as 2, 5, 7, 8-tetrahydroxy-1, 4-naphthoquinone (IIa). Deoxyhelicobasin was isolated and the structure was elucidated as Ib. Biosynthesis of helicobasidin (Ia) was studied and its isoprenoid origin has been clarified.

  莫姆帕菌素（Helicobasidium mompa）的代谢产物莫姆帕菌素（mompain）的结构被确定为2, 5, 7, 8-四羟基-1, 4-萘醌（IIa）。脱氧莫姆帕菌素（deoxyhelicobasin）被分离出来，其结构被确定为Ib。莫姆帕菌素（Ia）的生物合成过程被研究，其异戊二烯来源也得到了澄清。
• First direct observation of tautomerism of monohydroxynaphthazarins by IR-spectroscopy
  作者：Valery P. Glazunov、Alla Ya. Tchizhova、Nataly D. Pokhilo、Victor Ph. Anufriev、George B. Elyakov

  DOI：10.1016/s0040-4020(02)00060-1

  日期：2002.2

  Some substituted monohydroxylated naphthazarins (5,8-dihydroxy-1,4-naphthoquinones) were synthesized and studied by IR-spectroscopy in aprotic organic solvents at ambient temperature. Two narrow stretching mode bands in the high frequency range 3540-3410 cm(-1) due to a beta-hydroxy group were observed; it was established that this effect was caused by tautomerism. This allowed the creation of a convenient and accurate method for the measurement of a small amount of tautomer engaged in rapid exchange with the principal tautomer. Solvent and substituent effects were estimated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of Echinamines A and B, the First Aminated Hydroxynaphthazarins Produced by the Sea Urchin <i>Scaphechinus </i><i>m</i><i>irabilis</i> and Its Analogues
  作者：Nataly D. Pokhilo、Maria I. Shuvalova、Maxim V. Lebedko、Galina I. Sopelnyak、Alla Ya. Yakubovskaya、Natalia P. Mischenko、Sergey A. Fedoreyev、Victor Ph. Anufriev

  DOI：10.1021/np0502185

  日期：2006.8.1

  The first total synthesis of two marine aminated hydroxynaphthazarins, echinamines A (3-amino-7-ethyl- 2,5,6,8-tetrahydroxy-1,4- naphthoquinone) and B (2-amino-7-ethyl- 3,5,6,8-tetrahydroxy-1,4- naphthoquinone), produced by the sea urchin Scaphechinus mirabilis is described. This was achieved from 1,2,4-triacetoxybenzene (13) through a sequence involving double Fries rearrangement of 13, reduction of 3,5-diacetyl-1,2,4-trihydroxybenzene (14), methylation of 3,5-diethyl-1,2,4- trihydroxybenzene (15), simultaneous double acylation of 3,5-diethyl-1,2,4- trimethoxybenzene ( 16) with a dichloromaleic anhydride-ethyl radical elimination process, methylation of 6,7-dichloro-3-ethyl-2-hydroxynaphthazarin (17), nucleophilic substitution of a chlorine atom by the methoxy group in 6,7-dichloro-3-ethyl-2-methoxynaphthazarin (18), introduction of an amino group via direct substitution of a chlorine atom in 7-chloro-3-ethyl-2,6- dimethoxy- (11) and 7-chloro-2-ethyl-3,6-dimethoxynaphthazarins (12) by an azido group, and functional group deprotection. The synthesis of amino analogues of spinazarin and spinochrome D is also described.