2,3-二溴-1,4-二甲氧基-萘 | 72214-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,3-二溴-1,4-二甲氧基-萘
• 英文名称: 2,3-dibromo-1,4-dimethoxy-naphthalene
• 英文别名: 2,3-Dibromo-1,4-dimethoxynaphthalene
• CAS: 72214-03-0
• 化学式: C₁₂H₁₀Br₂O₂
• 分子量: 346.018
• InChiKey: LMTRUESPPIPPLL-UHFFFAOYSA-N

物化性质

• 熔点：
  119.5-121.0 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  397.9±37.0 °C(Predicted)
• 密度：
  1.696±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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

• 作为反应物：
  描述：

  2,3-二溴-1,4-二甲氧基-萘 在 copper(l) iodide 、 四(三苯基膦)钯 哌啶 、 potassium fluoride 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 水 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 68.5h， 生成 1,4-Dihydro-1,4-dioxonaphtho<3,4-b>cyclodec-3-ene-1,5-diyne
  参考文献：
  名称：

  Arene 1,4-Diradical Formation from o-Dialkynylarenes

  摘要：

  A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-l,l-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones. Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect. The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 degrees C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 degrees C.

  DOI：

  10.1021/jo00096a057
• 作为产物：
  描述：

  2,3-二溴-1,4-萘醌 在 sodium hydroxide 、 sodium dithionite 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 生成 2,3-二溴-1,4-二甲氧基-萘
  参考文献：
  名称：

  Anodic oxidation of 1,4-dimethoxy aromatic compounds. A facile route to functionalized quinone bisketals

  摘要：

  DOI：

  10.1021/jo01291a001

文献信息

• Ruthenium(0) Catalyzed Endiyne−α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C–C Bond Forming Transfer Hydrogenation
  作者：Aakarsh Saxena、Felix Perez、Michael J. Krische

  DOI：10.1021/jacs.5b02755

  日期：2015.5.13

  Upon exposure of 3,4-benzannulated 1,5-diynes (benzo-endiynes) to alpha-ketols (alpha-hydroxyketones) in the presence of Ru(0) catalysts derived from Ru-3(CO)(12) and RuPhos or CyJohnPhos, successive redox-triggered C-C coupling occurs to generate products of [4 + 2] cycloaddition. The proposed catalytic mechanism involves consecutive alkyne-carbonyl oxidative couplings to form transient oxaruthanacycles that suffer alpha-ketol mediated transfer hydrogenolysis. This process provides a new, convergent means of assembling Type II polyketide substructures.
• Arene 1,4-diradical formation from o-dialkynylarenes
  作者：M.F. Semmelhack、Thomas Neu、Francisco Foubelo

  DOI：10.1016/s0040-4039(00)92066-5

  日期：1992.6

  A series of five arene and quinone derivatives with dialkynyl substituents in the ortho positions and fixed in a 10-membered ring were prepared and tested with respect to thermal rearrangement to the corresponding arene 1,4 diradicals.
• Using NBS as a Mild Bromination Reagent for Polyalkoxyaromatic Systems
  作者：James L. Bloomer、Wei Zheng

  DOI：10.1080/00397919808007185

  日期：1998.6

  N-Bromosuccinimide in Methylene Chloride is A Mild Mono- or Dibromination Reagent for Polyalkoxyaromatic Compounds Including Those Which are too Labile to be Brominated with Molecular Bromine.
• 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
• 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.