2-benzyloxymethyl-3-bromo-1,4-dimethoxynaphthalene | 364729-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-benzyloxymethyl-3-bromo-1,4-dimethoxynaphthalene
• 英文别名: 2-Bromo-1,4-dimethoxy-3-(phenylmethoxymethyl)naphthalene
• CAS: 364729-00-0
• 化学式: C₂₀H₁₉BrO₃
• 分子量: 387.273
• InChiKey: WIIFZGLCWGWXTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-benzyloxymethyl-3-bromo-1,4-dimethoxynaphthalene 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.43h， 生成 Tert-butyl 3-[1,4-dioxo-3-(phenylmethoxymethyl)naphthalen-2-yl]-3-hydroxypropanoate
  参考文献：
  名称：

  Concise Synthesis of a Lactonamycin Model System by Diastereoselective Dihydroxylation of a Highly Functionalized Naphthoquinone

  摘要：

  [GRAPHICS]In this Letter, we describe an approach to the highly functionalized tetracycle 6, a model compound corresponding to the CDEF ring system contained in the recently discovered antibiotic lactonamycin. Our approach features an unprecedented, highly stereoselective dihydroxylation of quinone 13a, which leads directly to spirocyclic lactone 15, following acid-promoted deprotection/cyclization. The methodology described herein paves the way for a concise, highly diastereo- and enantioselective synthesis of the natural product.

  DOI：

  10.1021/ol016361g
• 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 10.75h， 生成 2-benzyloxymethyl-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

• 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.
• Concise Synthesis of a Lactonamycin Model System by Diastereoselective Dihydroxylation of a Highly Functionalized Naphthoquinone
  作者：Christopher Cox、Samuel J. Danishefsky

  DOI：10.1021/ol016361g

  日期：2001.9.1

  [GRAPHICS]In this Letter, we describe an approach to the highly functionalized tetracycle 6, a model compound corresponding to the CDEF ring system contained in the recently discovered antibiotic lactonamycin. Our approach features an unprecedented, highly stereoselective dihydroxylation of quinone 13a, which leads directly to spirocyclic lactone 15, following acid-promoted deprotection/cyclization. The methodology described herein paves the way for a concise, highly diastereo- and enantioselective synthesis of the natural product.