2,2,2-trichloroethyl 8-[4-[(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-enyl]phenyl]naphthalene-1-carboxylate | 163628-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,2-trichloroethyl 8-[4-[(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-enyl]phenyl]naphthalene-1-carboxylate
• CAS: 163628-74-8
• 化学式: C₂₄H₁₆Cl₆O₄
• 分子量: 581.107
• InChiKey: QEEIMHKTFKDDMN-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2,2,2-trichloroethyl 8-[4-[(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-enyl]phenyl]naphthalene-1-carboxylate 在 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 1.5h， 以79%的产率得到8-[4-[(E)-2-carboxyethenyl]phenyl]naphthalene-1-carboxylic acid
  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：

  8-碘-1-萘酸 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 草酰氯 、 sodium hydride 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 67.58h， 生成 2,2,2-trichloroethyl 8-[4-[(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-enyl]phenyl]naphthalene-1-carboxylate
  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

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.