2-(4-bromo-2,5-dipropoxyphenyl)-5,5-dimethyl[1,3]dioxane | 862974-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-bromo-2,5-dipropoxyphenyl)-5,5-dimethyl[1,3]dioxane
• 英文别名: 2-(4-Bromo-2,5-dipropoxyphenyl)-5,5-dimethyl-1,3-dioxane
• CAS: 862974-52-5
• 化学式: C₁₈H₂₇BrO₄
• 分子量: 387.314
• InChiKey: SQPJRBGJOYSQLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-2,5-dipropoxyphenyl)-5,5-dimethyl[1,3]dioxane 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 四溴化碳 、 potassium tert-butylate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 6.34h， 生成 4-(2-{5-[2-(4-methoxyphenyl)vinyl]thiophen-2-yl}vinyl)-2,5-dipropoxybenzaldehyde
  参考文献：
  名称：

  Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells

  摘要：

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-{2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

  DOI：

  10.1021/jo0506783
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 、 4-bromo-2,5-dipropoxybenzaldehyde 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到2-(4-bromo-2,5-dipropoxyphenyl)-5,5-dimethyl[1,3]dioxane
  参考文献：
  名称：

  Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells

  摘要：

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-{2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

  DOI：

  10.1021/jo0506783

文献信息

• Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells
  作者：Mikkel Jørgensen、Frederik C. Krebs

  DOI：10.1021/jo0506783

  日期：2005.7.1

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.