2-hydroxyethyl phenylpropiolate | 698354-39-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hydroxyethyl phenylpropiolate
• 英文别名: 2-Hydroxyethyl 3-phenylprop-2-ynoate
• CAS: 698354-39-1
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: RRKGONOHQYHIIX-UHFFFAOYSA-N

物化性质

• 沸点：
  334.4±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl phenylpropiolate 、 胆固醇甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以84.4%的产率得到2-(cholesteryloxycarbonyl)ethyl phenylpropiolate
  参考文献：
  名称：

  Helical Conjugated Polymers:  Synthesis, Stability, and Chiroptical Properties of Poly(alkyl phenylpropiolate)s Bearing Stereogenic Pendants

  摘要：

  Chiral poly(alkyl phenylpropiolate)s -{(C6H5)C=C[CO2(CH2)(2)OCOR*]}(n)- with R* = (S)(+)-[1-(6-methoxy-2-naphthyl)ethyl (P1), (1R,2S,5R)-(-)-menthoxymethyl (P2), (S)-(+)-(alpha-acetoxy)benzyl (P3), and cholesteryloxy (P4) were synthesized, and their structures and properties were investigated. The monomers [C6H5C-CCO2(CH2)(2)OCOR*; 1-4] were prepared by esterifications of stereogenic acids 8-10 or chloroformate (11) with 3-hydroxyethyl phenylpropiolate (7) in high yields. Polymerizations of 1-4 were effected by MoCl5-Ph4Sn at 60 or 80 degreesC, and polymers with high molecular weights (M-w up to similar to100 X 10(3)) were obtained in moderate yields. The polymers were characterized by IR, NMR, TGA, UV, and CD analyses. All of the polymers are stable, losing little of their weights when heated to greater than or equal to 300 degreesC and undergoing no chain scissions when annealed in air at greater than or equal to 150 degreesC. The macromolecular chains take helical conformations with preferred handedness, and their helical chirality can be reversibly tuned by solvent or temperature to varying extents.

  DOI：

  10.1021/ma048960j
• 作为产物：
  描述：

  乙二醇 、 苯丙炔酸 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以50.8%的产率得到2-hydroxyethyl phenylpropiolate
  参考文献：
  名称：

  Helical Conjugated Polymers:  Synthesis, Stability, and Chiroptical Properties of Poly(alkyl phenylpropiolate)s Bearing Stereogenic Pendants

  摘要：

  Chiral poly(alkyl phenylpropiolate)s -{(C6H5)C=C[CO2(CH2)(2)OCOR*]}(n)- with R* = (S)(+)-[1-(6-methoxy-2-naphthyl)ethyl (P1), (1R,2S,5R)-(-)-menthoxymethyl (P2), (S)-(+)-(alpha-acetoxy)benzyl (P3), and cholesteryloxy (P4) were synthesized, and their structures and properties were investigated. The monomers [C6H5C-CCO2(CH2)(2)OCOR*; 1-4] were prepared by esterifications of stereogenic acids 8-10 or chloroformate (11) with 3-hydroxyethyl phenylpropiolate (7) in high yields. Polymerizations of 1-4 were effected by MoCl5-Ph4Sn at 60 or 80 degreesC, and polymers with high molecular weights (M-w up to similar to100 X 10(3)) were obtained in moderate yields. The polymers were characterized by IR, NMR, TGA, UV, and CD analyses. All of the polymers are stable, losing little of their weights when heated to greater than or equal to 300 degreesC and undergoing no chain scissions when annealed in air at greater than or equal to 150 degreesC. The macromolecular chains take helical conformations with preferred handedness, and their helical chirality can be reversibly tuned by solvent or temperature to varying extents.

  DOI：

  10.1021/ma048960j