3-(2-hydroxy-5-methoxyphenyl)-3-phenethylcyclobutanone | 953792-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(2-hydroxy-5-methoxyphenyl)-3-phenethylcyclobutanone
• 英文别名: 3-(2-Hydroxy-5-methoxyphenyl)-3-(2-phenylethyl)cyclobutan-1-one
• CAS: 953792-77-3
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: FEQAREJFJNLBLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxy-5-methoxyphenyl)-3-phenethylcyclobutanone 在 [Rh(OH)(cod)]2 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 重水 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Asymmetric Synthesis of 3,4-Dihydrocoumarins by Rhodium-Catalyzed Reaction of 3-(2-Hydroxyphenyl)cyclobutanones

  摘要：

  3,4-Dihydrocoumarin derivatives were synthesized in a highly enantioselective manner from 3-(2-hydroxyphenyl)cyclobutanones through enantioselective carbon-carbon bond cleavage. A cascade reaction with electron-deficient alkenes introduced a carbon-carbon bond at the 5-position of the dihydrocoumarins.

  DOI：

  10.1021/ja075141g
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 3-(2-hydroxy-5-methoxyphenyl)-3-phenethylcyclobutanone
  参考文献：
  名称：

  Asymmetric Synthesis of 3,4-Dihydrocoumarins by Rhodium-Catalyzed Reaction of 3-(2-Hydroxyphenyl)cyclobutanones

  摘要：

  3,4-Dihydrocoumarin derivatives were synthesized in a highly enantioselective manner from 3-(2-hydroxyphenyl)cyclobutanones through enantioselective carbon-carbon bond cleavage. A cascade reaction with electron-deficient alkenes introduced a carbon-carbon bond at the 5-position of the dihydrocoumarins.

  DOI：

  10.1021/ja075141g

文献信息

• Palladium-Catalyzed Sequential Carbon−Carbon Bond Cleavage/Formation Producing Arylated Benzolactones
  作者：Takanori Matsuda、Masanori Shigeno、Masahiro Murakami

  DOI：10.1021/ol802218a

  日期：2008.11.20

  3-(2-Hydroxyphenyl)cyclobutanones react with aryl bromides in the presence of palladium catalysts to afford 4-arylmethyl-3,4-dihydrocoumarins in high yields through a sequence involving carbon-carbon bond cleavage and formation. In the case of the reaction with 2-(2-hydroxyphenyl)cyclobutanones, five- or seven-membered lactones were produced depending on the presence of an additional substituent at

  3-（2-羟基苯基）环丁酮在钯催化剂的存在下与芳基溴化物反应，通过涉及碳-碳键裂解和形成的序列，以高收率得到4-芳基甲基-3,4-二氢香豆素。在与2-（2-羟苯基）环丁酮反应的情况下，取决于在2-位上是否存在另外的取代基，产生了五元或七元内酯。
• Asymmetric Synthesis of 3,4-Dihydrocoumarins by Rhodium-Catalyzed Reaction of 3-(2-Hydroxyphenyl)cyclobutanones
  作者：Takanori Matsuda、Masanori Shigeno、Masahiro Murakami

  DOI：10.1021/ja075141g

  日期：2007.10.1

  3,4-Dihydrocoumarin derivatives were synthesized in a highly enantioselective manner from 3-(2-hydroxyphenyl)cyclobutanones through enantioselective carbon-carbon bond cleavage. A cascade reaction with electron-deficient alkenes introduced a carbon-carbon bond at the 5-position of the dihydrocoumarins.