(E)-6-hydroxy-1-(4-(trifluoromethyl)phenyl)but-2-en-1-one | 1158843-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-6-hydroxy-1-(4-(trifluoromethyl)phenyl)but-2-en-1-one
• 英文别名: (E)-4-hydroxy-1-[4-(trifluoromethyl)phenyl]but-2-en-1-one
• CAS: 1158843-58-3
• 化学式: C₁₁H₉F₃O₂
• 分子量: 230.186
• InChiKey: CIYNKIYTZXSLLB-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-6-hydroxy-1-(4-(trifluoromethyl)phenyl)but-2-en-1-one 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 17.0h， 生成 2-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)spiro[cyclopropane-1,2'-indene]-1',3'-dione
  参考文献：
  名称：

  Base promoted synthesis of activated cyclopropanes bearing homologated carbonyl groups via tandem Michael addition–intramolecular enolate trapping

  摘要：

  δ-羟基烯酮衍生的二苯基膦酸盐与 1,3-茚二酮进行了简单的碱促进分子内迈克尔引发的闭环反应，从而以良好的收率合成了具有同源羰基的新型活化环丙烷。使用金鸡纳树衍生物作为促进剂，可实现良好的对映选择性。

  DOI：

  10.1039/c1ob06487h
• 作为产物：
  描述：

  2-(oxiran-2-yl)-1-(4-(trifluoromethyl)phenyl)ethan-1-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到(E)-6-hydroxy-1-(4-(trifluoromethyl)phenyl)but-2-en-1-one
  参考文献：
  名称：

  3-Alkanoylprop-2-en-1-ol 衍生物的立体选择性制备

  摘要：

  通过β,γ-环氧酮与胺的开环反应立体选择性地制备了3-烷酰基丙-2-烯-1-醇衍生物。

  DOI：

  10.1055/s-0028-1087930

文献信息

• Asymmetric Synthesis of 1,3-Oxazolidines via Intramolecular Aza-Michael Addition by Bifunctional Organocatalysts
  作者：Yukihiro Fukata、Keisuke Asano、Seijiro Matsubara

  DOI：10.1246/cl.121245

  日期：2013.4.5

  A novel synthetic route to optically active 1,3-oxazolidines via formal [3 + 2] cycloaddition in the presence of cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. This protocol gives easy access to a wide range of chiral 1,3-oxazolidines. In addition, the results show that bifunctional organocatalysts can effect the intramolecular aza-Michael addition, leading to the asymmetric synthesis of nitrogen-containing heterocycles.

  报告了一种通过在金鸡纳碱-硫脲基双功能有机催化剂存在下，进行形式[3 + 2]环加成合成光学活性1,3-氧杂环戊烷的新合成路线。该方法便于获得广泛的手性1,3-氧杂环戊烷。此外，结果表明，双功能有机催化剂能够实现分子内氮杂Michael加成，从而导致氮含杂环的非对称合成。
• Asymmetric Synthesis of 1,3-Dioxolanes by Organocatalytic Formal [3 + 2] Cycloaddition via Hemiacetal Intermediates
  作者：Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol3003755

  日期：2012.3.16

  A novel asymmetric formal [3 + 2] cycloaddition reaction for the synthesis of 1,3-dioxolanes using cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. The reaction proceeds via the formation of hemiacetal intermediates between γ-hydroxy-α,β-unsaturated ketones and aldehydes.

  报道了一种使用金鸡纳生物碱-硫脲基双功能有机催化剂合成1,3-二氧戊环的新型不对称形式[3 + 2]环加成反应。该反应通过在γ-羟基-α，β-不饱和酮和醛之间形成半缩醛中间体而进行。
• Procedure-Controlled Enantioselectivity Switch in Organocatalytic 2-Oxazolidinone Synthesis
  作者：Yukihiro Fukata、Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ja407027e

  日期：2013.8.21

  In a novel organocatalytic formal [3 + 2] cycloaddition to afford chiral 2-oxazolidinones, an enantioselectivity switch could be induced by changing the manner of addition of the reactants, even when the reaction components (cinchona-alkaloid-derived aminothiourea catalyst, substrates, and solvent) were the same.
• Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile
  作者：Naoki Yoneda、Ayano Hotta、Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol503104b

  日期：2014.12.5

  Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to gamma-hydroxy-alpha,beta-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into beta-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of alpha,beta-unsaturated carbonyl compounds.
• Stereoselective Preparation of 3-Alkanoylprop-2-en-1-ol Derivatives
  作者：Seijiro Matsubara、Mutsumi Sada、Shizue Ueno、Keisuke Asano、Kenichi Nomura

  DOI：10.1055/s-0028-1087930

  日期：——

  3-Alkanoylprop-2-en-1-ol derivatives were prepared stereoselectively by ring-opening reaction of β,γ-epoxyketone with amines.

  通过β,γ-环氧酮与胺的开环反应立体选择性地制备了3-烷酰基丙-2-烯-1-醇衍生物。