3-(thiophen-3-yl)cyclohexan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(thiophen-3-yl)cyclohexan-1-one
• 英文别名: 3-thiophen-3-ylcyclohexanone；3-(3'-thienyl)cyclohexanone；3-Thiophen-3-ylcyclohexan-1-one
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: HXZRGZRUJZSNBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 3-噻吩三氟硼酸钾 在 acetylacetonatodicarbonylrhodium(l) 1,4-双(二苯基膦)丁烷 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以76%的产率得到3-(thiophen-3-yl)cyclohexan-1-one
  参考文献：
  名称：

  Potassium Alkenyl- and Aryltrifluoroborates:  Stable and Efficient Agents for Rhodium-Catalyzed Addition to Aldehydes and Enones

  摘要：

  [GRAPHICS]Potassium alkenyl- and aryltrifluoroborates undergo addition to enones and aldehydes in the presence of Rh(1) catalysts to give beta-functionalized ketones and allylic/benzylic alcohols, respectively. Reaction proceeds more rapidly than with the corresponding boronic acids, and the choice of phosphine ligand does not signifcantly influence the overall efficiency of addition.

  DOI：

  10.1021/ol9910767

文献信息

• 1,4-Addition of aryl boronic acids to α,β-unsaturated ketones catalyzed by a CCC–NHC pincer rhodium complex
  作者：Sean W. Reilly、Hannah K. Box、Glenn R. Kuchenbeiser、Ramel J. Rubio、Christopher S. Letko、Kandarpa D. Cousineau、T. Keith Hollis

  DOI：10.1016/j.tetlet.2014.09.107

  日期：2014.12

  An air- and water-stable CCC–NHC pincer Rh complex catalyzed the 1,4-addition of aryl boronic acids to α,β-unsaturated ketones and aldehydes. This bench top method proceeds in eco-friendly solvents including methanol and water. The scope of boronic acids was expanded to include heterocyclic examples.

  空气和水稳定的CCC-NHC夹心Rh络合物催化芳基硼酸向α，β-不饱和酮和醛的1,4-加成反应。这种台式方法是在包括甲醇和水在内的环保溶剂中进行的。硼酸的范围扩大到包括杂环实例。
• Heteroarylboronates in Rhodium-Catalyzed 1,4-Addition to Enones
  作者：Fabian Albrecht、Oliver Sowada、Meryem Fistikci、Mike M. K. Boysen

  DOI：10.1021/ol502630w

  日期：2014.10.3

  Rhodium(I)-catalyzed 1,4-addition of aryl and alkenylboronic acids to alpha,beta-unsaturated carbonyl compounds is well established, but the transfer of heteroaryl residues in this reaction remains underdeveloped. We have studied heteroaryl MIDA and pinacol boronates as alternatives to the labile boronic acid counterparts. Under racemic conditions, 12 adducts with heteroaryl residues, among them unsubstituted 3- and 4-pyridinyl, 2-furanyl, thienyl, and pyrrolyl groups, were obtained in moderate to excellent yields. The enantioselective version of the reaction proved highly sensitive to the electronic character of the heteroaryl substituents, with boronates carrying electron-rich residues giving modest to high yields but consistently high enantiomeric excesses.