2-(1,3-dioxolan-2-yl)-1,4-dimethoxynaphthalene | 75265-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,3-dioxolan-2-yl)-1,4-dimethoxynaphthalene
• 英文别名: 2-(1,4-Dimethoxynaphthalen-2-yl)-1,3-dioxolane
• CAS: 75265-10-0
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: NRYOUKLSQUIYKP-UHFFFAOYSA-N

物化性质

• 熔点：
  109.2 °C
• 沸点：
  411.3±45.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxolan-2-yl)-1,4-dimethoxynaphthalene 在 氯 作用下， 反应 0.03h， 生成 2,3-dichloro-1,4-dimethoxy-naphthalene
  参考文献：
  名称：

  Hypervalent Iodine Chemistry:  Mechanistic Investigation of the Novel Haloacetoxylation, Halogenation, and Acetoxylation Reactions of 1,4-Dimethoxynaphthalenes

  摘要：

  Treatment of 1,4-dimethoxynaphthalenes with iodosobenzene diacetate and trimethylsilyl chloride or bromide furnished the haloacetoxylated, acetoxylated, and halogenated 1,4-dimethoxynaphthalenes in excellent yield. The reaction pathway for each transformation was shown to be a function of reagent stoichiometry. A mechanistic hypothesis is presented that rationalizes the reaction pathways and explains the subtle differences in the halogenation reactions. The acetoxylation, for example, is thought to involve the formation of an iodonium ion that promotes the nucleophilic addition of acetate ion and subsequent 1,2-acetyl migration. Bromination occurs as a direct result of the oxidation of trimethylsilyl bromide to bromine, followed by electrophilic aromatic substitution. Chlorination is thought to proceed via a radical process and not the formation of molecular chlorine from the dissociation of iodosobenzene dichloride. The haloacetoxylation reaction also appears to be fairly specific for 1,4-dimethoxynaphthalenes, since the analogous reaction with a 1,4-dimethoxybenzene derivative was unsuccessful.

  DOI：

  10.1021/jo970525i
• 作为产物：
  描述：

  1,4-二羟基萘 在 potassium carbonate 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 丙酮 、 苯 为溶剂， 反应 28.0h， 生成 2-(1,3-dioxolan-2-yl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride

  摘要：

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。

  DOI：

  10.1055/s-1999-2875

文献信息

• Short synthesis of functionalized pentalongin derivatives using pyridinium ylid chemistry
  作者：Pieter Claes、Jan Jacobs、Sven Claessens、Norbert De Kimpe

  DOI：10.1016/j.tet.2010.07.012

  日期：2010.8

  of acylmethylnaphthoquinones. The latter naphthoquinones were prepared starting from 2-dioxolanylnaphthoquinone by means of both a stoichiometric and a catalytic method deploying various pyridinium ylids.

  通过酰基甲基萘醌的环化反应，合成了在C-1具有乙缩醛功能的3-取代的五聚体衍生物。后者的萘醌是从2-二氧戊环基萘醌开始，通过化学计量的和催化的方法，采用各种吡啶鎓碘化物来制备的。
• SYNTHESIS OF NOVEL QUINONES WITH SILVER (II) DIPICOLINATE AS A NEW SELECTIVE OXIDANT
  作者：Krystian Kloc、Jacek Mlochowski、Ludwik Syper

  DOI：10.1246/cl.1980.725

  日期：1980.6.5

  and naphthoquinones bearing oxiranyl or 1,3-dioxolan-2-yl substituents were prepared by oxidative demethylation of appropriate hydroquinone dimethyl ethers with silver (II) dipicolinate. A remarkable selectivity of this silver (II) complex as an oxidizing reagent was demonstrated.

  带有环氧乙烷基或 1,3-二氧戊环-2-基取代基的苯并和萘醌是通过适当的氢醌二甲醚与吡啶二羧酸银 (II) 的氧化去甲基化制备的。证明了这种银 (II) 络合物作为氧化剂的显着选择性。
• Novel haloacetoxylation of 1,4-dimethoxynaphthalenes using hypervalent iodine chemistry
  作者：P.Andrew Evans、Thomas A. Brandt

  DOI：10.1016/0040-4039(96)01427-x

  日期：1996.9

  Treatment of 1,4-dimethoxynaphthalenes with iodosobenzene and trimethylsilyl chloride or bromide furnished the corresponding 2,3-haloacetoxylated-1,4-dimethoxynaphthalenes. Copyright (C) 1996 Elsevier Science Ltd
• KLOC K.; MLOCHOWSKI J.; SYPER L., CHEM. LETT., 1980, NO 6, 725-728
  作者：KLOC K.、 MLOCHOWSKI J.、 SYPER L.

  DOI：——

  日期：——
• Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride
  作者：Ayumi Tomatsu、Syunji Takemura、Kimiko Hashimoto、Masaya Nakata

  DOI：10.1055/s-1999-2875

  日期：1999.9

  The oxidative demethylation of 1,4-dimethoxynaphthalene and 1,4-dimethoxybenzene derivatives with cobalt(III) fluoride proceeded in good to excellent yield to afford the corresponding naphthoquinone and benzoquinone derivatives.

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。