9,10-dihydrobenzocycloocten-7(8H)-one | 144744-96-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 9,10-dihydrobenzocycloocten-7(8H)-one
• 英文别名: (5Z)-9,10-dihydro-8H-benzo[8]annulen-7-one
• CAS: 144744-96-7
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: XMPUUPGDXQBCIH-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(o-styryl)cyclobutanone 在 ytterbium(III) triflate 作用下， 以 氯苯 为溶剂， 反应 8.0h， 以64%的产率得到9,10-dihydrobenzocycloocten-7(8H)-one
  参考文献：
  名称：

  Acids Direct 2-Styrylcyclobutanone into Two Distinctly Different Reaction Pathways

  摘要：

  Two structurally distinct carbocycles were selectively obtained by the reactions of 2-(o-styryl)cyclobutanones promoted by ytterbium salts. Treatment of the cyclobutanones with YbCl3 in 1,4-dioxane at 100 degrees C afforded 2-(2-chloroethyl)naphthalenes. On the other hand, the reaction with Yb(OTf)(3) in chlorobenzene at 130 degrees C gave 9,10-dihydrobenzocycloocten-7(8H)-ones.

  DOI：

  10.1021/ol0506922

文献信息

• Free radical annulation of dichlorocyclobutanones with sequential ring expansion
  作者：Paul Dowd、Wei Zhang、Steven J. Geib

  DOI：10.1016/0040-4020(95)00093-n

  日期：1995.3

  reaction of dichloroketene with 1,5-dienes undergo intramolecular free radical annulation. Lewis acid-promoted ring-opening of the cyclized cyclobutanones then yields novel ring expansion products. Reaction of (R)-carvone provides an unusual example leading to the formation of a tricyclic dione. The carbonyl group of carvone enhances the radical cyclization and influences the ring-opening pathway.

  描述了一种新的合成序列，该序列在1，5-二烯的末端添加了烯酮的元素。由二氯乙烯酮与1，5-二烯反应产生的二氯环丁酮加合物经历分子内自由基环化。然后路易斯酸促进环化环丁酮的开环，产生新的扩环产物。（R）-香芹酮的反应提供了导致形成三环二酮的不寻常的例子。香芹酮的羰基增强自由基环化并影响开环途径。
• Eight-membered Ring Formation via Olefin Insertion into a Carbon–Carbon Single Bond
  作者：Takanori Matsuda、Atsushi Fujimoto、Mitsuru Ishibashi、Masahiro Murakami

  DOI：10.1246/cl.2004.876

  日期：2004.7

  Treatment of cyclobutanone having an o-styryl group at the 2-position with a catalytic amount of rhodium–phosphine complex afforded eight-membered ring ketones via intramolecular insertion of the C...

  用催化量的铑-膦配合物处理2-位具有邻苯乙烯基的环丁酮，通过C的分子内插入得到八元环酮...
• Novel free radical ring-forming reaction of dichlorocyclobutanones and sequential ring expansion
  作者：Paul Dowd、Wei Zhang

  DOI：10.1021/ja00051a064

  日期：1992.12