(3bα,7aα)-3-acetyl-2,3b,4,7,7a,8a-hexahydro-8a-methyl-cyclopentinden-8(1H)-one | 142421-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3bα,7aα)-3-acetyl-2,3b,4,7,7a,8a-hexahydro-8a-methyl-cyclopentinden-8(1H)-one
• 英文别名: (4aS,8aR)-1-acetyl-3a-methyl-2,3,4a,5,8,8a-hexahydrocyclopenta[a]inden-4-one
• CAS: 142421-80-5；142507-39-9
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: AFSFCMHGTCDBMN-ZVORSSOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-2-(3-戊炔-1-基)-1,3-二氧戊环 、 [双环[4.2.0]辛-3,7-二烯-7,8-二基二(氧基)]二(三甲基硅烷) 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以44%的产率得到(3bα,7aα)-3-acetyl-2,3b,4,7,7a,8a-hexahydro-8a-methyl-cyclopentinden-8(1H)-one
  参考文献：
  名称：

  Ring-Enlarging Annulations. A One-Step Conversion of Cyclic Silyl Acyloins and .omega.-Alkynyl Acetals to Polycyclic Enediones

  摘要：

  new sequence of cationic reactions that converts cyclic silyl acyloins and omega-alkynyl acetals to polycyclic enediones is reported. For example, treatment of bis-1,2-((trimethylsilyl)oxy)cyclobutene and 2-(ethylenedioxy)-5-heptyne with excess boron trifluoride etherate in methylene chloride for 2 days provides 4-acetyl-3,5,6,6a-tetrahydro-6a-methyl-1-(2H)-pentalenone in 58% yield. This product is formed via a sequence involving a Mukaiyama aldol reaction, a pinacol ring expansion, and a 5-exo-dig alkynyl ketone cyclization. In the case of terminal alkynes, the last cyclization occurs in a 6-endo-dig fashion. The scope and limitations of this process are studied, and a number of bi- and tricyclic ring systems are formed.

  DOI：

  10.1021/jo00107a011

文献信息

• Annulative ring expansions. Direct conversion of .omega.-alkynyl acetals to polycyclic unsaturated ketones
  作者：Joseph Sisko、Aaron Balog、Dennis P. Curran

  DOI：10.1021/jo00042a007

  日期：1992.7

  Geminal acylation of omega-acetylenic acetals and bis(silyloxy)cycloalkenes under Lewis acid conditions preceded cationic cyclization of the alkyne onto the ketone to produce polycyclic unsaturated ketones.