4-bromo-2,5-dipropoxybenzaldehyde | 243970-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromo-2,5-dipropoxybenzaldehyde
• 英文别名: 4-Brom-2,5-dipropoxybenzaldehyd
• CAS: 243970-08-3
• 化学式: C₁₃H₁₇BrO₃
• 分子量: 301.18
• InChiKey: KEHUXNCZAIPRIL-UHFFFAOYSA-N

物化性质

• 沸点：
  387.4±42.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2,5-dipropoxybenzaldehyde 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 四溴化碳 、 potassium tert-butylate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 7.34h， 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：

  1,4-二正丙氧基苯 在 正丁基锂 、 溴 作用下， 以 乙醚 、 正庚烷 为溶剂， 生成 4-bromo-2,5-dipropoxybenzaldehyde
  参考文献：
  名称：

  Meier, Herbert; Aust, Harald, Journal fur Praktische Chemie (Weinheim), 1999, vol. 341, # 5, p. 466 - 471

  摘要：

  DOI：

文献信息

• Crown ethers in the OPV series
  作者：Dirk Schwöppe、Bernhard Beile、Herbert Meier

  DOI：10.3998/ark.5550190.p007.988

  日期：——

  4-phenylenevinylene)s (trimers, tetramers and a nonamer), which contain 1-3 (E)-stilbene crowns. A classical reaction route led first to stilbene crown subunits. Wittig-Horner reactions of diphosphonates with mono- or dialdehydes or of dialdehydes with mono- or diphosphonates yielded then the desired all-trans configured OPVs, which were designed for the complexation of metal cations.

  本论文涉及低聚（1,4-亚苯基亚乙烯基）（三聚体、四聚体和九聚体）的合成，其中包含 1-3 (E)-二苯乙烯冠。经典的反应路线首先导致二苯乙烯冠亚基。二膦酸酯与单或二醛或二醛与单或二膦酸酯的 Wittig-Horner 反应产生所需的全反式构型 OPV，其设计用于络合金属阳离子。
• Structural Requirements for Palladium Catalyst Transfer on a Carbon–Carbon Double Bond
  作者：Masataka Nojima、Yoshihiro Ohta、Tsutomu Yokozawa

  DOI：10.1021/jacs.5b03113

  日期：2015.5.6

  Intramolecular transfer of (Bu3PPd)-Bu-t(0) on a carbon carbon double bond (C=C) was investigated by using Suzuki-Miyaura coupling reaction of dibromostilbenes with aryl boronic acid or boronic acid esters in the presence of various additives containing C=C as a model. Substituent groups at the ortho position of C=C of stilbenes are critical for selective intramolecular catalyst transfer and may serve to suppress formation of the bimolecular C=C-Pd-C=C complex that leads to intermolecular transfer of (Bu3PPd)-Bu-t(0).