2-((2-methylallyloxy)methyl)-3-bromo-1,4-dimethoxynaphthalene | 415949-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((2-methylallyloxy)methyl)-3-bromo-1,4-dimethoxynaphthalene
• 英文别名: 3-bromo-2-(2-methylallyloxymethyl)-1,4-dimethoxynaphthalene；2-Bromo-1,4-dimethoxy-3-(2-methylprop-2-enoxymethyl)naphthalene
• CAS: 415949-89-2
• 化学式: C₁₇H₁₉BrO₃
• 分子量: 351.24
• InChiKey: WKPMHVYEZNKBHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((2-methylallyloxy)methyl)-3-bromo-1,4-dimethoxynaphthalene 在 copper(l) iodide 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 12.5h， 生成 2-(2-methylallyloxymethyl)-3-trifluoromethyl-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of 2-alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones

  摘要：

  2-Alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones were conveniently synthesized in two steps by treatment of 2-substituted-3-bromo-1,4-dimethoxynaphthalene with CF3COONa/CuI and subsequent dealkylative oxidation by treatment with cerium(IV) ammonium nitrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00791-8
• 作为产物：
  描述：

  1,4-二羟基-2-甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 丙酮 为溶剂， 反应 10.5h， 生成 2-((2-methylallyloxy)methyl)-3-bromo-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of 2-alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones

  摘要：

  2-Alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones were conveniently synthesized in two steps by treatment of 2-substituted-3-bromo-1,4-dimethoxynaphthalene with CF3COONa/CuI and subsequent dealkylative oxidation by treatment with cerium(IV) ammonium nitrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00791-8

文献信息

• Palladium catalyzed intramolecular cascade type cyclizations: interesting Approach towards naphthoquinone derivatives having an O-containing heterocyclic skeleton
  作者：Sukla Nandi、Raju Singha、Jayanta K. Ray

  DOI：10.1016/j.tet.2014.12.016

  日期：2015.1

  Important naphthoquinones fused with an O-containing six-, seven- and eight-membered ring along with one tetracyclic compound, which are normally difficult to construct, have been synthesized using intramolecular Heck reaction where 6-exo trig, 7-endo trig and 8-endo trig cyclizations take place, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of 2-alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones
  作者：Nguyen Van Tuyen、Bart Kesteleyn、Norbert De Kimpe

  DOI：10.1016/s0040-4020(01)00791-8

  日期：2002.1

  2-Alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones were conveniently synthesized in two steps by treatment of 2-substituted-3-bromo-1,4-dimethoxynaphthalene with CF3COONa/CuI and subsequent dealkylative oxidation by treatment with cerium(IV) ammonium nitrate. (C) 2002 Elsevier Science Ltd. All rights reserved.