(E)-3-(3,4-diheptoxyphenyl)prop-2-enoic acid | 183787-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-diheptoxyphenyl)prop-2-enoic acid
• CAS: 183787-63-5
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: AUDASCYCKLXODC-JQIJEIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-diheptoxyphenyl)prop-2-enoic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Photopolymerization of Carbohydrate-Based Discotic Mesogens. Syntheses and Phase Properties of 1,2,3,4,6-Penta-O-(trans-3,4-dialkoxycinnamoyl)-(d)- glucopyranoses and Their Oligomers

  摘要：

  The neat phase properties of the alpha and beta anomers of 1,2,3,4,6-penta-O-(trans-3,4-dialkoxycinnamoyl) (D)-glucopyranose (n alpha GP and n beta GP; n, the number of carbon atoms in the alkyl chains, is 6-8, 10, and 14) have been investigated by optical microscopy, differential scanning calorimetry, and X-ray powder diffraction. Each of the GP forms an enantiotropic and thermotropic discotic columnar liquid-crystalline phase. Irradiation of the 14GP in dilute solutions leads to two intramolecular [2 + 2] cycloaddition reactions between cinnamoyl double bonds. In the solid I (obtained by recrystallization from solvent and in which 14GP molecules are paired in each columnar stack) and ''isotropic'' melt phases, only short (<10 monomer unit), probably branched oligomers form upon irradiation due to the continued preference for intramolecular cycloadditions and the ability of each monomer to interact with more than two neighbors. Irradiation of the solid II phase (obtained by cooling the liquid-crystalline phase) provides unbranched oligomers with <20 monomer units. However; more than 30 14 alpha GP monomer units have been linked in unbranched chains upon irradiation of its liquid-crystalline phase. This is the greatest degree of columnar polymerization reported to date from a discotic mesophase. Qualitatively similar results are obtained upon irradiation of other GP in their various phases. Oligomerization of GP liquid-crystalline and solid I phases is intracolumnar, and the columnar packing arrangement of-the monomers is retained to ca. 100 degrees C above their clearing temperatures; each GP produces nanoscale cylinders of one diameter but varying lengths. The oligomers unwind and do not retake their original form when they are dissolved and reprecipitated or heated to above their clearing temperatures and cooled. The nature of the oligomerization processes is discussed, especially with regard to inter-/intramolecular and inter-/intracolumnar competitions for [2 + 2] cycloaddition reactions and the possibility of an anomeric effect on oligomer length.

  DOI：

  10.1021/ja961665x
• 作为产物：
  描述：

  1-溴代庚烷 在 吡啶 、 potassium carbonate 、 二正丙胺 作用下， 以 丁酮 为溶剂， 反应 25.5h， 生成 (E)-3-(3,4-diheptoxyphenyl)prop-2-enoic acid
  参考文献：
  名称：

  Photopolymerization of Carbohydrate-Based Discotic Mesogens. Syntheses and Phase Properties of 1,2,3,4,6-Penta-O-(trans-3,4-dialkoxycinnamoyl)-(d)- glucopyranoses and Their Oligomers

  摘要：

  The neat phase properties of the alpha and beta anomers of 1,2,3,4,6-penta-O-(trans-3,4-dialkoxycinnamoyl) (D)-glucopyranose (n alpha GP and n beta GP; n, the number of carbon atoms in the alkyl chains, is 6-8, 10, and 14) have been investigated by optical microscopy, differential scanning calorimetry, and X-ray powder diffraction. Each of the GP forms an enantiotropic and thermotropic discotic columnar liquid-crystalline phase. Irradiation of the 14GP in dilute solutions leads to two intramolecular [2 + 2] cycloaddition reactions between cinnamoyl double bonds. In the solid I (obtained by recrystallization from solvent and in which 14GP molecules are paired in each columnar stack) and ''isotropic'' melt phases, only short (<10 monomer unit), probably branched oligomers form upon irradiation due to the continued preference for intramolecular cycloadditions and the ability of each monomer to interact with more than two neighbors. Irradiation of the solid II phase (obtained by cooling the liquid-crystalline phase) provides unbranched oligomers with <20 monomer units. However; more than 30 14 alpha GP monomer units have been linked in unbranched chains upon irradiation of its liquid-crystalline phase. This is the greatest degree of columnar polymerization reported to date from a discotic mesophase. Qualitatively similar results are obtained upon irradiation of other GP in their various phases. Oligomerization of GP liquid-crystalline and solid I phases is intracolumnar, and the columnar packing arrangement of-the monomers is retained to ca. 100 degrees C above their clearing temperatures; each GP produces nanoscale cylinders of one diameter but varying lengths. The oligomers unwind and do not retake their original form when they are dissolved and reprecipitated or heated to above their clearing temperatures and cooled. The nature of the oligomerization processes is discussed, especially with regard to inter-/intramolecular and inter-/intracolumnar competitions for [2 + 2] cycloaddition reactions and the possibility of an anomeric effect on oligomer length.

  DOI：

  10.1021/ja961665x

文献信息

• Photopolymerization of Carbohydrate-Based Discotic Mesogens. Syntheses and Phase Properties of 1,2,3,4,6-Penta-<i>O</i>-(<i>trans</i>-3,4-dialkoxycinnamoyl)-(<scp>d</scp>)- glucopyranoses and Their Oligomers
  作者：Ravindranath Mukkamala、Charles L. Burns,、Robert M. Catchings、Richard G. Weiss

  DOI：10.1021/ja961665x

  日期：1996.1.1

  The neat phase properties of the alpha and beta anomers of 1,2,3,4,6-penta-O-(trans-3,4-dialkoxycinnamoyl) (D)-glucopyranose (n alpha GP and n beta GP; n, the number of carbon atoms in the alkyl chains, is 6-8, 10, and 14) have been investigated by optical microscopy, differential scanning calorimetry, and X-ray powder diffraction. Each of the GP forms an enantiotropic and thermotropic discotic columnar liquid-crystalline phase. Irradiation of the 14GP in dilute solutions leads to two intramolecular [2 + 2] cycloaddition reactions between cinnamoyl double bonds. In the solid I (obtained by recrystallization from solvent and in which 14GP molecules are paired in each columnar stack) and ''isotropic'' melt phases, only short (<10 monomer unit), probably branched oligomers form upon irradiation due to the continued preference for intramolecular cycloadditions and the ability of each monomer to interact with more than two neighbors. Irradiation of the solid II phase (obtained by cooling the liquid-crystalline phase) provides unbranched oligomers with <20 monomer units. However; more than 30 14 alpha GP monomer units have been linked in unbranched chains upon irradiation of its liquid-crystalline phase. This is the greatest degree of columnar polymerization reported to date from a discotic mesophase. Qualitatively similar results are obtained upon irradiation of other GP in their various phases. Oligomerization of GP liquid-crystalline and solid I phases is intracolumnar, and the columnar packing arrangement of-the monomers is retained to ca. 100 degrees C above their clearing temperatures; each GP produces nanoscale cylinders of one diameter but varying lengths. The oligomers unwind and do not retake their original form when they are dissolved and reprecipitated or heated to above their clearing temperatures and cooled. The nature of the oligomerization processes is discussed, especially with regard to inter-/intramolecular and inter-/intracolumnar competitions for [2 + 2] cycloaddition reactions and the possibility of an anomeric effect on oligomer length.