1-(1,4-二羟基-8-甲氧基萘-2-基)乙酮 | 83662-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(1,4-二羟基-8-甲氧基萘-2-基)乙酮
• 英文名称: 2-acetyl-1,4-dihydroxy-8-methoxynaphthalene
• 英文别名: Ethanone, 1-(1,4-dihydroxy-8-methoxy-2-naphthalenyl)-；1-(1,4-dihydroxy-8-methoxynaphthalen-2-yl)ethanone
• CAS: 83662-31-1
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: WJLUOLVLSLETQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1,4-二羟基-8-甲氧基萘-2-基)乙酮 在 lithium aluminium tetrahydride 、 diazabicyclononane 、 硝酸 、 三氯化硼 、 三氟乙酸 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2H-Furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione, 3,3a,5,11b-tetrahydro-7-hydroxy-5-methyl-
  参考文献：
  名称：

  Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol

  摘要：

  DOI：

  10.1021/jo00168a013
• 作为产物：
  描述：

  5,8-diacetoxy-1,4-ethano-1,4-dihydro-1-methoxynaphthalene 在 三氟化硼乙醚 作用下， 反应 0.67h， 生成 1-(1,4-二羟基-8-甲氧基萘-2-基)乙酮
  参考文献：
  名称：

  3-乙酰基-5-甲氧基-1,4-萘醌的合成。一种新方法

  摘要：

  摘要 开发了一种新的、高效的 3-乙酰基-5-甲氧基-1,4-萘醌合成方法。该合成尤其涉及乙酰化狄尔斯-阿尔德加合物的热解和区域特异性弗里斯重排反应。

  DOI：

  10.1080/00397919408012620

文献信息

• Non-Catalyzed Thermal Reactions of Acylquinones with Allylstannanes
  作者：Kazuhiro Maruyama、Yoshihiro Matano

  DOI：10.1246/bcsj.62.3877

  日期：1989.12

  Thermal reactions of acylquinones with allylstannanes in benzene afforded several kinds of product after column chromatography on silica gel; acyl allyl quinones, acyl allyl epoxy quinones, cyclopentanoid compounds including stannyl moiety, allyl hydroxy quinones, acyl hydroquinones, and acyl allyl hydroquinones. The main product comprises cyclopentanoid compounds, which are novel [2+3] cyclo adducts with 1,2-migration of trialkylstannyl moiety. Spectroscopic examinations (1H NMR and Vis-UV) enabled us to confirm the reaction pathways that four types of precursors were initially generated via polarized tight pair and inverted to isolated products during purification by column chromatography. Similar reactions in acetonitrile showed a remarkable difference in the reactivity, that is, acyl allyl quinones and the corresponding hydroquinones are obtained, but the [2+3] cyclo adducts are not produced at all. From 1H NMR examination, it was confirmed that three types of precursor are generated via solvent separated ion pairs at the initial stage. The rather strong reactivity of acylquinones towards allylstannanes will be due to electron withdrawing ability of acyl group.

  酰基喹诺酮与烯丙基锡在苯中的热反应经过硅胶柱层析后产生了几种产品；包括酰基烯丙基喹诺酮、酰基烯丙基环氧喹诺酮、含锡基团的环戊烷类化合物、烯丙基羟基喹诺酮、酰基羟基喹诺酮和酰基烯丙基羟基喹诺酮。主要产品是环戊烷类化合物，它们是新型的 [2+3] 环加成物，具有三烷基锡基团的 1,2-迁移。通过光谱学检查（1H NMR 和 Vis-UV），我们确认了反应途径，四种前体最初通过极化紧配对生成，并在柱层析纯化过程中转化为孤立的产品。在乙腈中的类似反应显示出明显的反应性差异，即生成酰基烯丙基喹诺酮及其对应的羟基喹诺酮，但完全不产生 [2+3] 环加成物。从 1H NMR 检查中确认，三种类型的前体在初始阶段通过溶剂分离离子对生成。酰基喹诺酮对烯丙基锡的较强反应性将是由于酰基的电子吸引能力。
• An Annulation Reaction to Naphthalene-1,4-diols Using Dimethyl Phthalide-3-phosphonates.
  作者：Mitsuaki WATANABE、Hitoshi MORIMOTO、Kayoko NOGAMI、Saori IJICHI、Sunao FURUKAWA

  DOI：10.1248/cpb.41.968

  日期：——

  A regioselective annulation to naphthalene ring systems from dimethyl phthalide-3-phosphonates and electron-deficient olefins is described.

  描述了一种从二甲基苯二酸酯-3-膦酸酯和电子缺乏的烯烃中选择性合成萘环体系的区域选择性环化反应。
• An abnormal fries rearrangement induced by a -methoxyl group in monoacetates of naphthohydroquinones.
  作者：Trevor A. Chorn、Robin G.F. Giles、Ivan R. Green、Victor I. Hugo、Peter R.K. Mitchell

  DOI：10.1016/s0040-4039(00)87597-8

  日期：1982.1

  The acetyl group of two 1-acetoxy-4-hydroxy-5-methoxynaphthalenes migrates to C-3 on treatment with boron trifluoride etherate.

  在用三氟化硼醚化物处理时，两个1-乙酰氧基-4-羟基-5-甲氧基萘的乙酰基迁移到C-3。
• Synthesis of deoxyfrenolicin and nanaomycin A
  作者：George A. Kraus、Maria Teresa Molina、John A. Walling

  DOI：10.1021/jo00383a018

  日期：1987.4
• A General Approach to Angucyclines: Synthesis of Hatomarubigin A, Rubiginone B2, Antibiotic X-1488E, 6-Hydroxytetrangulol, and Tetrangulol
  作者：Kathlyn A Parker、Qing-jie Ding

  DOI：10.1016/s0040-4020(00)00869-3

  日期：2000.12

  Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxy-tetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd. All rights reserved.