1,3-bisbromomethyl-2-methoxynaphthalene | 194999-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bisbromomethyl-2-methoxynaphthalene
• 英文别名: 1,3-Bis(bromomethyl)-2-methoxynaphthalene
• CAS: 194999-66-1
• 化学式: C₁₃H₁₂Br₂O
• 分子量: 344.046
• InChiKey: FSJNYWNXVHPGFD-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  399.5±32.0 °C(Predicted)
• 密度：
  1.665±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-bisbromomethyl-2-methoxynaphthalene 在 氢氧化钾 、 硫脲 作用下， 以 乙醇 、 二甲基亚砜 、 苯 为溶剂， 反应 29.0h， 生成 cisoid-anti-11,22-dimethoxy-2,13-dithia-[3.3](1,3)naphthalenophane
  参考文献：
  名称：

  Synthesis of Dibenzopyrenes and Pyrenes via Photolytic Sulfur Extrusion and Intramolecular Cross-Coupling Reactions of Dithia[3.3](1,3)naphthalenophanes and Dithia[3.3]metacyclophanes

  摘要：

  The syntheses of several substituted dithia[3.3]metacyclophanes and dithia[3.3](1,3)naphthalenophanes are reported and their photolyses in triethyl or trimethyl phosphite are described. Under these conditions, the corresponding tetrahydrodibenzopyrenes and tetrahydropyrenes are produced in a one-pot procedure when the precursor dithianaphthalenophanes and dithiacyclophanes possess at least one intraannular methoxyl group. A mechanism with supporting evidence is proposed to account for these results. Structural determinations of the four isomeric 11,22-dimethoxy-2,13-dithia[3.3](1,3)naphthalenophanes by NMR and X-ray single-crystal diffraction studies are also described. The syntheses of the novel anti-transoid- and anti-cisoid-[2.2](1,3)naphthalenophanes are also described.

  DOI：

  10.1021/jo970181w
• 作为产物：
  描述：

  聚合甲醛 、 3-甲氧基-2-萘甲醇 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 36.0h， 以49%的产率得到1,3-bisbromomethyl-2-methoxynaphthalene
  参考文献：
  名称：

  Synthesis of Dibenzopyrenes and Pyrenes via Photolytic Sulfur Extrusion and Intramolecular Cross-Coupling Reactions of Dithia[3.3](1,3)naphthalenophanes and Dithia[3.3]metacyclophanes

  摘要：

  The syntheses of several substituted dithia[3.3]metacyclophanes and dithia[3.3](1,3)naphthalenophanes are reported and their photolyses in triethyl or trimethyl phosphite are described. Under these conditions, the corresponding tetrahydrodibenzopyrenes and tetrahydropyrenes are produced in a one-pot procedure when the precursor dithianaphthalenophanes and dithiacyclophanes possess at least one intraannular methoxyl group. A mechanism with supporting evidence is proposed to account for these results. Structural determinations of the four isomeric 11,22-dimethoxy-2,13-dithia[3.3](1,3)naphthalenophanes by NMR and X-ray single-crystal diffraction studies are also described. The syntheses of the novel anti-transoid- and anti-cisoid-[2.2](1,3)naphthalenophanes are also described.

  DOI：

  10.1021/jo970181w

文献信息

• Palladium catalyzed cross-coupling between phenyl- or naphthylboronic acids and benzylic bromides
  作者：Sultan Chowdhury、Paris E. Georghiou

  DOI：10.1016/s0040-4039(99)01566-x

  日期：1999.10

  The Suzuki-Miyaura palladium-catalyzed coupling reaction was extended to achieve mixed cross-coupling between substituted aryl and naphthyl mono- and bisbromomethanes with phenylboronic acid, 1-methoxy-2-naphthyl-, 3-methoxy-2-naphthyl-, or 4-methoxy-1-naphthylboronic acid to form the corresponding disubstituted methanes.

  扩展了Suzuki-Miyaura钯催化的偶联反应，以实现取代的芳基和萘基单和双溴甲烷与苯基硼酸，1-甲氧基-2-萘基，3-甲氧基-2-萘基或4的混合交叉偶联。 -甲氧基-1-萘基硼酸形成相应的二取代甲烷。