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.
• Anodic oxidation of 1,4-dimethoxy aromatic compounds. A facile route to functionalized quinone bisketals
  作者：Daniel R. Henton、Richard A. McCreery、John S. Swenton

  DOI：10.1021/jo01291a001

  日期：1980.2
• 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