1,4-bis[[tri(prop-2-yl)silyl]ethynyl]naphthalene-2,3-diol | 1426074-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-bis[[tri(prop-2-yl)silyl]ethynyl]naphthalene-2,3-diol
• 英文别名: 1,4-Bis[2-tri(propan-2-yl)silylethynyl]naphthalene-2,3-diol；1,4-bis[2-tri(propan-2-yl)silylethynyl]naphthalene-2,3-diol
• CAS: 1426074-00-1
• 化学式: C₃₂H₄₈O₂Si₂
• 分子量: 520.903
• InChiKey: LEEFWVBLJZPPHM-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C (decomp)
• 沸点：
  558.5±50.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis[[tri(prop-2-yl)silyl]ethynyl]naphthalene-2,3-diol 、 2,3-dichlorobenzo[g]quinoxaline 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以73%的产率得到5,16-bis[[tri(prop-2-yl)silyl]ethynyl]benzo[g]naphtho[2',3':5,6][1,4]dioxinoxino[2,3-b]quinoxaline
  参考文献：
  名称：

  Alkynylated Diazadioxaacenes: Syntheses and Properties

  摘要：

  We report the successful synthesis of a series of ethynylated dioxadiazaacenes and investigate their properties. We developed a modular Cu-based catalytic procedure to build up [1,4]dioxino[2,3-b]pyrazine motifs starting from only a few building blocks. TIPS-acetylene-substituted benzene-1,2-diol and naphthalene-2,3-diol were reacted with 2,3-dichloropyrazine, 2,3-dichloroquinoxaline, and 2,3-dichlorobenzoquinoxaline to give a set of six novel and well-soluble dioxadiazaacenes. Different reaction conditions for the coupling were tested. Copper catalysis is most effective and gave the best yield of dioxadiazaacenes. The resulting azaoxaacenes were characterized in terms of optical and electronic properties and crystal packing.

  DOI：

  10.1021/jo400092r
• 作为产物：
  描述：

  2,3-二甲氧基萘 在 copper(l) iodide 、 四(三苯基膦)钯 、 溴 、 三溴化硼 、 三乙胺 、 二异丙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 41.75h， 生成 1,4-bis[[tri(prop-2-yl)silyl]ethynyl]naphthalene-2,3-diol
  参考文献：
  名称：

  Alkynylated Diazadioxaacenes: Syntheses and Properties

  摘要：

  We report the successful synthesis of a series of ethynylated dioxadiazaacenes and investigate their properties. We developed a modular Cu-based catalytic procedure to build up [1,4]dioxino[2,3-b]pyrazine motifs starting from only a few building blocks. TIPS-acetylene-substituted benzene-1,2-diol and naphthalene-2,3-diol were reacted with 2,3-dichloropyrazine, 2,3-dichloroquinoxaline, and 2,3-dichlorobenzoquinoxaline to give a set of six novel and well-soluble dioxadiazaacenes. Different reaction conditions for the coupling were tested. Copper catalysis is most effective and gave the best yield of dioxadiazaacenes. The resulting azaoxaacenes were characterized in terms of optical and electronic properties and crystal packing.

  DOI：

  10.1021/jo400092r