2,4-Bis(bromomethyl)-1-methoxynaphthalene | 171815-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,4-Bis(bromomethyl)-1-methoxynaphthalene
• CAS: 171815-39-7
• 化学式: C₁₃H₁₂Br₂O
• 分子量: 344.046
• InChiKey: XWHAPKUCGFCCQT-UHFFFAOYSA-N

物化性质

• 沸点：
  411.0±35.0 °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：

  2,4-Bis(bromomethyl)-1-methoxynaphthalene 在 三氟乙酸 calcium carbonate 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 51.0h， 生成 10,20,30,34-Tetramethoxynonacyclo[31.7.1.13,11.113,21.123,31.04,9.014,19.024,29.035,40]tetratetraconta-1(41),3(44),4,6,8,10,13(43),14,16,18,20,23(42),24,26,28,30,33,35,37,39-icosaene
  参考文献：
  名称：

  Syntheses of Calix[4]naphthalenes Derived from 1-Naphthol

  摘要：

  Using a convergent synthetic strategy, the synthesis of the previously elusive C-4v-symmetrical calix[4]naphthalene from 1-naphthol is described. Using other independent convergent routes, syntheses of the other three isomeric calix[4]naphthalenes originally formed from the direct base-catalyzed condensation of formaldehyde with 1-naphthol are also described. All of these methods involved either a TiCl4- or TFA-assisted coupling reaction to achieve the cyclization steps. A mechanism is proposed to account for the formation of the original three isomeric calix[4]naphthalenes from the base-catalyzed condensation of formaldehyde with 1-naphthol.

  DOI：

  10.1021/jo00127a038
• 作为产物：
  描述：

  2,4-Bis(hydroxymethyl)-1-methoxynaphthalene 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 72.0h， 以21%的产率得到2,4-Bis(bromomethyl)-1-methoxynaphthalene
  参考文献：
  名称：

  Syntheses of Calix[4]naphthalenes Derived from 1-Naphthol

  摘要：

  Using a convergent synthetic strategy, the synthesis of the previously elusive C-4v-symmetrical calix[4]naphthalene from 1-naphthol is described. Using other independent convergent routes, syntheses of the other three isomeric calix[4]naphthalenes originally formed from the direct base-catalyzed condensation of formaldehyde with 1-naphthol are also described. All of these methods involved either a TiCl4- or TFA-assisted coupling reaction to achieve the cyclization steps. A mechanism is proposed to account for the formation of the original three isomeric calix[4]naphthalenes from the base-catalyzed condensation of formaldehyde with 1-naphthol.

  DOI：

  10.1021/jo00127a038

文献信息

• 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
  作者：Muhammad Ashram、David O. Miller、John N. Bridson、Paris E. Georghiou

  DOI：10.1021/jo970181w

  日期：1997.9.1

  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.
• Syntheses of Calix[4]naphthalenes Derived from 1-Naphthol
  作者：Paris E. Georghiou、Muhammad Ashram、Zhaopeng Li、Steven G. Chaulk

  DOI：10.1021/jo00127a038

  日期：1995.11

  Using a convergent synthetic strategy, the synthesis of the previously elusive C-4v-symmetrical calix[4]naphthalene from 1-naphthol is described. Using other independent convergent routes, syntheses of the other three isomeric calix[4]naphthalenes originally formed from the direct base-catalyzed condensation of formaldehyde with 1-naphthol are also described. All of these methods involved either a TiCl4- or TFA-assisted coupling reaction to achieve the cyclization steps. A mechanism is proposed to account for the formation of the original three isomeric calix[4]naphthalenes from the base-catalyzed condensation of formaldehyde with 1-naphthol.