3-(5-chloro-2-hydroxyphenyl)cyclobutanone | 294669-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(5-chloro-2-hydroxyphenyl)cyclobutanone
• 英文别名: 3-(5-Chloro-2-hydroxyphenyl)cyclobutan-1-one
• CAS: 294669-31-1
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: GQBDXGKFXADTQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-chloro-2-hydroxyphenyl)cyclobutanone 在 [Rh(OH)(cod)]2 、 (S)-(-)-5,5-双(二苯膦基)-4,4-双-1,3-苯并间二氧杂环戊烯 作用下， 以 甲苯 为溶剂， 以85%的产率得到6-氯-4-甲基-3,4-二氢色烯-2-酮
  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-(5-chloro-2-hydroxyphenyl)cyclobutanone
  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

• Lactone Formation by Rhodium-Catalyzed C−C Bond Cleavage of Cyclobutanone
  作者：Masahiro Murakami、Takuo Tsuruta、Yoshihiko Ito

  DOI：10.1002/1521-3773(20000717)39:14<2484::aid-anie2484>3.0.co;2-1

  日期：2000.7.17
• 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.