α-bromo-9-(p-methoxybenzylidene)xanthene | 87712-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: α-bromo-9-(p-methoxybenzylidene)xanthene
• 英文别名: 9-[Bromo(4-methoxyphenyl)methylidene]-9H-xanthene；9-[bromo-(4-methoxyphenyl)methylidene]xanthene
• CAS: 87712-58-1
• 化学式: C₂₁H₁₅BrO₂
• 分子量: 379.253
• InChiKey: YCBAVKZFRJFNTO-UHFFFAOYSA-N

物化性质

• 沸点：
  476.4±45.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  α-bromo-9-(p-methoxybenzylidene)xanthene 在 silver carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 168.0h， 以60%的产率得到11-(p-methoxyphenyl)dibenzoxepin-10-one
  参考文献：
  名称：

  Vinylic cations from solvolysis. 39. Solvolysis of 9-[.alpha.-bromo- and .alpha.-(tosyloxy)-p-methoxybenzylidene]xanthenes

  摘要：

  DOI：

  10.1021/jo00175a015
• 作为产物：
  描述：

  占吨酮 在 溴 作用下， 以 四氯化碳 、 乙醚 、 苯 为溶剂， 反应 6.0h， 生成 α-bromo-9-(p-methoxybenzylidene)xanthene
  参考文献：
  名称：

  Vinylic cations from solvolysis. 39. Solvolysis of 9-[.alpha.-bromo- and .alpha.-(tosyloxy)-p-methoxybenzylidene]xanthenes

  摘要：

  DOI：

  10.1021/jo00175a015

文献信息

• 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.
• Vinylic cations from solvolysis. 39. Solvolysis of 9-[.alpha.-bromo- and .alpha.-(tosyloxy)-p-methoxybenzylidene]xanthenes
  作者：Zvi Rappoport、Joseph Kaspi、Dov Tsidoni

  DOI：10.1021/jo00175a015

  日期：1984.1