2,3-dichloro-1,4-dimethoxy-naphthalene | 41245-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dichloro-1,4-dimethoxy-naphthalene
• 英文别名: 2,3-Dichlor-1,4-dimethoxy-naphthalin；2,3-Dichloro-1,4-dimethoxynaphthalene
• CAS: 41245-40-3
• 化学式: C₁₂H₁₀Cl₂O₂
• 分子量: 257.116
• InChiKey: MTGKEIQJKJCFFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  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

文献信息

• Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous‐Flow Hydrogenation‐Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts
  作者：Hiroyuki Miyamura、Fumiya Tobita、Aya Suzuki、Shū Kobayashi

  DOI：10.1002/anie.201904159

  日期：2019.7

  Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi‐Al2O3)) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous‐flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation

  固定在二甲基聚硅烷上的Pt-Au双金属纳米颗粒催化剂（Pt-Au /（DMPSi-Al 2 O 3））已开发用于将醌选择性加氢为对苯二酚。在连续流动条件下证实了催化剂的高反应活性，选择性和坚固性。在连续和连续流动条件下成功进行了醌的各种直接衍生化反应，例如甲基化，乙酰化，三氟甲磺酰化，甲基丙烯酸化和苯甲酰化，以良好的产率提供了所需的产品，甚至具有优异的收率。尤其是，对空气敏感的氢醌，如蒽氢醌和萘氢醌，可以在封闭的连续和连续流动条件下成功生成并衍生化而不会分解。
• Byrde; Woodcock, Annals of Applied Biology, 1953, vol. 40, p. 675,677
  作者：Byrde、Woodcock

  DOI：——

  日期：——
• Inoue et al., Yuki Gosei Kagaku Kyokaishi, 1956, vol. 14, p. 622,624
  作者：Inoue et al.

  DOI：——

  日期：——
• Inoue et al., Bulletin of University of Osaka Prefecture, Series A: Engineering and Natural Sciences, 1959, vol. <A> 8, p. 31,34, 35
  作者：Inoue et al.

  DOI：——

  日期：——
• Hypervalent Iodine Chemistry:  Mechanistic Investigation of the Novel Haloacetoxylation, Halogenation, and Acetoxylation Reactions of 1,4-Dimethoxynaphthalenes
  作者：P. Andrew Evans、Thomas A. Brandt

  DOI：10.1021/jo970525i

  日期：1997.8.1

  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.