rac-(3aR,8aR)-6,7-bis(3-fluorophenyl)-8a-ethyl-1,2,3,3a,8,8a-hexahydroazulen-4(5H)-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: rac-(3aR,8aR)-6,7-bis(3-fluorophenyl)-8a-ethyl-1,2,3,3a,8,8a-hexahydroazulen-4(5H)-one
• 英文别名: (3aR,8aR)-8a-ethyl-6,7-bis(3-fluorophenyl)-1,2,3,3a,5,8-hexahydroazulen-4-one
• 化学式: C₂₄H₂₄F₂O
• 分子量: 366.451
• InChiKey: MQEGMLBIHNIPCV-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙基环己酮 、 1-乙炔基-3-氟苯 在 potassium hydroxide semihydrate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以50%的产率得到rac-(3aR,8aR)-6,7-bis(3-fluorophenyl)-8a-ethyl-1,2,3,3a,8,8a-hexahydroazulen-4(5H)-one
  参考文献：
  名称：

  Unexpected diastereoselective one-pot assembly of hexahydroazulenones from 2-alkylcyclohexanones and arylacetylenes in KOH/DMSO suspension

  摘要：

  2-Alkylcyclohexanones react with arylacetylenes (KOH/DMSO, 100 degrees C, 1 h) to afford unexpectedly hexahydroazulenones in 34-50% yields and ca. 100% diastereoselectivity (instead of the expected acetylenic alcohols), the minor products being isomeric arylethenyl ketones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.019

文献信息

• Unexpected diastereoselective one-pot assembly of hexahydroazulenones from 2-alkylcyclohexanones and arylacetylenes in KOH/DMSO suspension
  作者：Boris A. Trofimov、Elena Yu. Schmidt、Elena V. Skitaltseva、Nadezhda V. Zorina、Nadezhda I. Protsuk、Igor A. Ushakov、Albina I. Mikhaleva、Oleg A. Dyachenko、Olga N. Kazheva、Grigorii G. Aleksandrov

  DOI：10.1016/j.tetlet.2011.06.019

  日期：2011.8

  2-Alkylcyclohexanones react with arylacetylenes (KOH/DMSO, 100 degrees C, 1 h) to afford unexpectedly hexahydroazulenones in 34-50% yields and ca. 100% diastereoselectivity (instead of the expected acetylenic alcohols), the minor products being isomeric arylethenyl ketones. (C) 2011 Elsevier Ltd. All rights reserved.