3,3-diethoxy-6-<2-(p-ethoxyphenyl)-2-phenylvinylidene>-1,4-cyclohexadiene | 128421-72-7

• 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: 3,3-diethoxy-6-<2-(p-ethoxyphenyl)-2-phenylvinylidene>-1,4-cyclohexadiene
• 英文别名: 3,3-diethoxy-6-(2'-(p-ethoxyphenyl)-2'-phenylethenylidene)-1,4-cyclohexadiene；3,3-diethoxy-6-[2-(4-ethoxyphenyl)-2-phenylethenylidene]cyclohexa-1,4-diene
• CAS: 128421-72-7
• 化学式: C₂₆H₂₈O₃
• 分子量: 388.507
• InChiKey: LCCCZMDBBJFQST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,3-diethoxy-6-<2-(p-ethoxyphenyl)-2-phenylvinylidene>-1,4-cyclohexadiene 、 盐酸 生成 2-(p-ethoxyphenyl)-2-phenyl-4'-ethoxyacetophenone
  参考文献：
  名称：

  KITAMURA, TSUGIO;NAKAMURA, ICHIZO;KABASHIMA, TAKASHI;KOBAYASHI, SHINJIRO;+, CHEM. LETT.,(1990) N, C. 9-12

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha-溴-beta,beta-二(4-乙氧基苯基)苯乙烯 、 sodium ethanolate 以58%的产率得到
  参考文献：
  名称：

  KITAMURA, TSUGIO;NAKAMURA, ICHIZO;KABASHIMA, TAKASHI;KOBAYASHI, SHINJIRO;+, CHEM. LETT.,(1990) N, C. 9-12

  摘要：

  DOI：

文献信息

• Ipso Substitution by Alkoxide Ions in Photolysis of Triarylvinyl Halides. Firm Evidence for Intervention of Vinyl Cations
  作者：Tsugio Kitamura、Ichizo Nakamura、Takashi Kabashima、Shinjiro Kobayashi、Hiroshi Taniguchi

  DOI：10.1246/cl.1990.9

  日期：1990.1

  Photolysis of 1-bromo-2, 2-bis(p-alkoxyphenyl)-1-phenylethenes in the presence of sodium ethoxide in ethanol gave ipso adducts bearing 1,2-aryl rearranged structure, indicating that ipso substitution proceeds via vinyl cations.

  1-bromo-2, 2-bis(p-alkoxyphenyl)-1-phenylethenes 在乙醇中的乙醇钠存在下光解得到带有 1,2-芳基重排结构的 ipso 加合物，表明 ipso 取代是通过乙烯基阳离子进行的。
• Ipso substitution of triarylvinyl cations by alkoxide anions
  作者：Tsugio Kitamura、Takashi Kabashima、Ichizo Nakamura、Tetsuro Fukuda、Hiroshi Taniguchi

  DOI：10.1021/ja00019a025

  日期：1991.9

  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.