3-(4-chloro-2,5-dimethoxyphenyl)prop-1-yne | 223433-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chloro-2,5-dimethoxyphenyl)prop-1-yne
• 英文别名: Vcfdncpsskiioo-uhfffaoysa-；1-chloro-2,5-dimethoxy-4-prop-2-ynylbenzene
• CAS: 223433-02-1
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: VCFDNCPSSKIIOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-2,5-dimethoxyphenyl)prop-1-yne 在 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.25h， 以25%的产率得到1,6-bis(4-chloro-2,5-dimethoxyphenyl)hexa-2,4-diyne
  参考文献：
  名称：

  Synthesis, X-ray Structure Analysis and Topochemical Photopolymerization of Substituted 1,6-Bis(2,5-dimethoxyphenyl)hexa-2,4-diynes

  摘要：

  The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<917::aid-ejoc917>3.0.co;2-b
• 作为产物：
  描述：

  1-bromo-4-chloro-2,5-dimethoxybenzene 在 magnesium 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 3-(4-chloro-2,5-dimethoxyphenyl)prop-1-yne
  参考文献：
  名称：

  Synthesis, X-ray Structure Analysis and Topochemical Photopolymerization of Substituted 1,6-Bis(2,5-dimethoxyphenyl)hexa-2,4-diynes

  摘要：

  The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<917::aid-ejoc917>3.0.co;2-b

文献信息

• Synthesis, X-ray Structure Analysis and Topochemical Photopolymerization of Substituted 1,6-Bis(2,5-dimethoxyphenyl)hexa-2,4-diynes
  作者：Hermann Irngartinger、Markus Skipinski

  DOI：10.1002/(sici)1099-0690(199904)1999:4<917::aid-ejoc917>3.0.co;2-b

  日期：1999.4

  The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.

表征谱图