1,6-bis(p-chlorophenoxy)-2,4-hexadiyne | 166271-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,6-bis(p-chlorophenoxy)-2,4-hexadiyne
• 英文别名: 1,6-bis(4-chlorophenoxy)-2,4-hexadiyne；1,6-bis(4-chlorophenoxy)hexa-2,4-diyne
• CAS: 166271-14-3
• 化学式: C₁₈H₁₂Cl₂O₂
• 分子量: 331.198
• InChiKey: ATQDWOLEFRKKET-UHFFFAOYSA-N

物化性质

• 沸点：
  497.6±40.0 °C(predicted)
• 密度：
  1.299±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,6-bis(p-chlorophenoxy)-2,4-hexadiyne 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以66%的产率得到6,6'-dichloro-3,3'-diiodo-2H,2'H-4,4'-bichromene
  参考文献：
  名称：

  ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2H-hydronaphthalene and chromene) and 2H-Quinoline Bearing an Alkenyl Iodide Moiety

  摘要：

  Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.

  DOI：

  10.1021/jo401922b
• 作为产物：
  描述：

  对氯苯酚 在 吡啶 、 四甲基乙二胺 、 氧气 、 potassium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,6-bis(p-chlorophenoxy)-2,4-hexadiyne
  参考文献：
  名称：

  ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2H-hydronaphthalene and chromene) and 2H-Quinoline Bearing an Alkenyl Iodide Moiety

  摘要：

  Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.

  DOI：

  10.1021/jo401922b

文献信息

• Ligand-Free Synthesis of 1,4-Disubstituted-1,3-diynes by Iron/Copper Cocatalyzed Homocoupling of Terminal Alkynes
  作者：Peipei Wang、Xiaoyan Liu、Songlin Zhang

  DOI：10.1002/cjoc.201200878

  日期：2013.2

  oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4‐disubstituted‐1,3‐diynes was presented. The results showed that both CuBr and FeCl3 played crucial roles in the reaction. It is noteworthy that this protocol employs mild, efficient, aerobic and ligand free conditions. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed into the corresponding 1

  提出了一种简单有效的方案，用于末端炔烃与对称的1,4-二取代-1,3-二炔的Fe / Cu共催化氧化均偶联反应。结果表明，CuBr和FeCl 3均在反应中起关键作用。值得注意的是，该方案采用温和，有效，有氧和无配体条件。炔烃（包括芳烃，杂芳烃和脂族炔烃）以良好或优异的收率转化为相应的1,3-二炔烃。