5,8-dihydroxy-2-methoxy-6,7-dichloro-1,4-naphthoquinone | 96127-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dihydroxy-2-methoxy-6,7-dichloro-1,4-naphthoquinone
• 英文别名: 6,7-dichloro-5,8-dihydroxy-2-methoxy-1,4-naphthoquinone；2-Methoxy-6,7-dichloronaphthazarin；6,7-dichloro-2-methoxynaphthazarin；6,7-dichloro-5,8-dihydroxy-2-methoxynaphthalene-1,4-dione
• CAS: 96127-20-7
• 化学式: C₁₁H₆Cl₂O₅
• 分子量: 289.072
• InChiKey: PXJSEIMTAGSHRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,8-dihydroxy-2-methoxy-6,7-dichloro-1,4-naphthoquinone 在 铁粉 、 氧气 作用下， 以 溶剂黄146 、 sodium hydroxide 为溶剂， 反应 0.17h， 以59%的产率得到5,8-二羟基-2-甲氧基-1,4-萘醌
  参考文献：
  名称：

  卤代萘甲素和醌茜素的还原脱卤是制备母体化合物的简单途径

  摘要：

  摘要 通过 2-氯-3-烷基-、2,3-二氯（二溴）-、三氯-（三溴）-和四氯（四溴）-萘并和 2,3-二氯喹吖啶与 Fe/HOAc 反应，然后氧化在温和碱性条件下的空气中，以良好至极好的收率获得了相应的萘并芴素。

  DOI：

  10.1080/00397919808007029
• 作为产物：
  描述：

  对苯二甲醚 在 manganese(IV) oxide 、 aluminum (III) chloride 、 硫酸 、 三乙胺 、 sodium chloride 作用下， 以 乙腈 为溶剂， 反应 24.8h， 生成 5,8-dihydroxy-2-methoxy-6,7-dichloro-1,4-naphthoquinone
  参考文献：
  名称：

  Spinochrome D 的合成，一种多种海胆物种的代谢物

  摘要：

  通过将 2,3-二氯萘扎林 (13) 氧化成 2-羟基-6,7-二氯萘扎林 (14)、14 的 O-甲基化、亲核取代，以 58% 的总产率合成了海胆代谢物棘色素 D (1)通过生成的 2-甲氧基-6,7-二氯萘扎林 (19) 中的 Cl 原子的 MeO 基团，水解得到的 2,3,6-三甲氧基萘扎林 (10)。

  DOI：

  10.1007/s10600-016-1597-4

文献信息

• Chemistry of naphthazarin derivatives. Transetherification selectivity of naphthazarin methoxy derivatives
  作者：N. D. Pokhilo、V. A. Denisenko、V. F. Anufriev

  DOI：10.1134/s1070428014050054

  日期：2014.5

  Transetherification of naphthazarin methoxy derivatives in basic conditions occurs only with primary monohydric alcohols. 1,3-Butanediol due to the assistance of the hydroxy group at the C1 atom gives rise to a mixture of transetherification products at the primary and secondary hydroxy groups in a ratio 3: 1. The reaction with methyl α-D-glucopyranoside affords predominantly methyl 6-O-(5,8-dihydroxy-1

  在基本条件下萘萘甲氧基衍生物的醚交换作用仅与伯一元醇发生。1,3-丁二醇由于在C 1原子上的羟基的辅助作用，在伯羟基和仲羟基上以3：1的比例生成了醚交换产物的混合物。与甲基α-D-吡喃葡萄糖苷反应得到主要是甲基6 - O-（5,8-二羟基-1,4-二氧杂萘-2-基）-α-D-吡喃葡萄糖苷，以前未知的水溶性萘醌-碳水化合物共轭物。
• 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。
• Selective Syntheses of 2-Alkylamino- and 2-Alkoxy-6,7-dichloro-5,8-dihydroxy-1,4-naphthoquinones
  作者：Masaru Matsuoka、Katsuhisa Hamano、Teijiro Kitao、Koichi Takagl

  DOI：10.1055/s-1984-31034

  日期：——
• 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.
• ——
  作者：V. P. Glazunov、A. Ya. Tchizhova、M. I. Shuvalova、V. Ph. Anufriev

  DOI：10.1023/a:1009581319518

  日期：——

  A set of substituted 2,6- and 2,7-dihydroxynaphthazarins were synthesized. The difference in the UV spectra of alkaline alcoholic solutions of 2,6- and 2,7-dihydroxynaphthazarins allows the reliable differentiation of the structures of these compounds. The IR spectra of 2,6- and 2,7-dihydroxynaphthazarins have characteristic nonoverlapping intervals of stretching vibration frequencies of the beta -hydroxy groups. Based on these spectral regularities, the data on cuculoquinone, which has been isolated previously from lichen Cetraria cucullata and has been identified as 7,7'-bis(3-ethyl-2,5,6,8-tetrahydroxynaphthalene-1,4-dione), were revised and the structure of 6,6 '-bis(3-ethyl-2,5,7,8-tetrahydroxynaphthalene- 1,4-dione) was assigned to this compound.