1-methoxy-1-(p-methoxyphenyl)-2,2-diphenylethene | 122127-41-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-methoxy-1-(p-methoxyphenyl)-2,2-diphenylethene
• 英文别名: 1-Methoxy-4-(1-methoxy-2,2-diphenylethenyl)benzene
• CAS: 122127-41-7
• 化学式: C₂₂H₂₀O₂
• 分子量: 316.4
• InChiKey: DEQWZEHRBHOCNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 1-(1-溴-2,2-二苯基乙烯基)-4-甲氧基苯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到1-methoxy-1-(p-methoxyphenyl)-2,2-diphenylethene
  参考文献：
  名称：

  Ipso substitution of triarylvinyl cations by alkoxide anions

  摘要：

  Photolysis and solvolysis of triarylbromoethanes 1 in the presence of alkoxide anions in alcohols resulted in significant formation of products derived from ipso substitution by alkoxide anions. Photolysis of 1-aryl-1-bromo-2,2-diphenylethenes 1Aa and 1Ab with 10 mol equiv of alkoxide anions gave 1-alkoxy-1-aryl-2,2-diphenylethenes 2A and 3,3-dialkoxy-6-(2,2-diphenylvinylidene)-1,4-cyclohexadienes 3A (ipso adducts). However, the photolysis with weak bases such as TEA, pyridine, NaHCO3, and K2CO3 did not give ipso adducts 3A but only enol ethers 2A. Interestingly, photolysis of 2,2-bis(p-alkoxyphenyl)-1-bromo-1-phenylethenes 4a and 4b with NaOEt in ethanol afforded ipso adducts 6a and 6b, respectively, which had a 1,2-aryl-rearranged structure. Furthermore, solvolysis of 1-bromo-1-(p-methoxyphenyl)ethenes 1Aa, 1Ba, and 1Ca in ethanol containing 10 mol equiv of NaOEt at 120-130-degrees-C for 1-3 days provided p-ethoxyphenyl-substituted enol ethers 2bb, p-ethoxyphenyl-substituted bromoethenes 1b, and p-methoxyphenyl-substituted enol ethers 2ab, respectively. The major formation of p-ethoxyphenyl-substituted compounds (ipso-substituted products) suggests that there is no large difference in ipso substitution between vinyl cations generated by photolysis and solvolysis. On the basis of the results obtained above the factors affecting ipso attack on arylvinyl cations are discussed.

  DOI：

  10.1021/ja00019a025

文献信息

• Drastic Base Dependence of Products in Photolysis of 1-(<i>p</i>-Methoxyphenyl)-2,2-diphenylvinyl Bromide. ipso Substitution by Alkoxide Ions
  作者：Tsugio Kitamura、Takashi Kabashima、Shinjiro Kobayashi、Hiroshi Taniguchi

  DOI：10.1246/cl.1988.1951

  日期：1988.12.5

  Addition of alkoxide ions resulted in ipso substitution in the photolysis of an alcohol solution of 1-(p-methoxyphenyl)-2,2-diphenylvinyl bromide, whereas addition of triethylamine, pyridine, or NaHCO3 led to vinylic substitution.

  醇盐离子的添加​​导致 1-(对甲氧基苯基)-2,2-二苯基溴乙烯醇溶液光解中的 ipso 取代，而三乙胺、吡啶或 NaHCO3 的添加导致乙烯基取代。
• Hori, Kenzi; Kamada, Hideki; Kitamura, Tsugio, Journal of the Chemical Society. Perkin transactions II, 1992, # 6, p. 871 - 877
  作者：Hori, Kenzi、Kamada, Hideki、Kitamura, Tsugio、Kobayashi, Shinjiro、Taniguchi, Hiroshi

  DOI：——

  日期：——