methyl 8-[4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl]naphthalene-1-carboxylate | 163628-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 8-[4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl]naphthalene-1-carboxylate
• CAS: 163628-76-0
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: UVRVGZRDSFJYBJ-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 8-[4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl]naphthalene-1-carboxylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(E)-3-(7-Oxo-7H-benzo[de]anthracen-9-yl)-acrylic acid methyl 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：

  methyl 8-iodo-1-naphthoate 在 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 methyl 8-[4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl]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.