Methyl 8-(4-formylphenyl)naphthalene-1-carboxylate | 199169-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 8-(4-formylphenyl)naphthalene-1-carboxylate
• CAS: 199169-30-7
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: XHLCUKGRYLCSGI-UHFFFAOYSA-N

物化性质

• 沸点：
  458.8±33.0 °C(predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 8-(4-formylphenyl)naphthalene-1-carboxylate 在 sodium hydride 作用下， 以 氘代苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 (1R,2R,3S,4S)-3,4-Bis-[4-(8-methoxycarbonyl-naphthalen-1-yl)-phenyl]-cyclobutane-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Toward Covalently Linked Organic Networks:  Model Studies and Connector Syntheses

  摘要：

  A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an alpha-truxillate-type cyclobutane photodimer in quantitative yield, Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of(pseudo)centrosymmetric attachment to polyvalent hubs, This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.

  DOI：

  10.1021/jo9714167
• 作为产物：
  描述：

  4-甲酰基苯硼酸 、 methyl 8-iodo-1-naphthoate 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 生成 Methyl 8-(4-formylphenyl)naphthalene-1-carboxylate
  参考文献：
  名称：

  Efficient Stereo- and Regiocontrolled Alkene Photodimerization through Hydrogen Bond Enforced Preorganization in the Solid State

  摘要：

  DOI：

  10.1021/jo00112a007

文献信息

• Efficient Stereo- and Regiocontrolled Alkene Photodimerization through Hydrogen Bond Enforced Preorganization in the Solid State
  作者：Ken S. Feldman、Robert F. Campbell

  DOI：10.1021/jo00112a007

  日期：1995.4
• Toward Covalently Linked Organic Networks:  Model Studies and Connector Syntheses
  作者：Ken S. Feldman、Robert F. Campbell、Joe C. Saunders、Chuljin Ahn、Katherine M. Masters

  DOI：10.1021/jo9714167

  日期：1997.12.1

  A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an alpha-truxillate-type cyclobutane photodimer in quantitative yield, Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of(pseudo)centrosymmetric attachment to polyvalent hubs, This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.