4-hydroxy-4-(2'-thiophenyl)butan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-4-(2'-thiophenyl)butan-2-one
• 英文别名: 4-hydroxy-4-(thiophen-2-yl)butan-2-one；4-Hydroxy-4-thiophen-2-ylbutan-2-one
• 化学式: C₈H₁₀O₂S
• 分子量: 170.232
• InChiKey: CBKHHNYPTUTINY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 二丙酮醇 在 三甲基铝 、 S-1,1'-联-2-萘酚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 43.0h， 以40%的产率得到4-hydroxy-4-(2'-thiophenyl)butan-2-one
  参考文献：
  名称：

  Catalytic aldol-transfer reactions with Al-alkoxide trapping

  摘要：

  Al-BINOL catalyzed aldol-transfer reactions of aldehydes with diacetonealcohol conducted with Al-alkoxide trapping gave aldol adducts in good yields. The best yields were obtained with electron-rich aromatic aldehydes (e.g., 83% yield with 3,4,5-trimethoxybenzaldehyde). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.044

文献信息

• Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water
  作者：Swapandeep Singh Chimni、Dinesh Mahajan

  DOI：10.1016/j.tet.2005.03.045

  日期：2005.5

  A synthetically useful pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes with ketones in water affords the aldol addition product in up to 93% yield. Electrophilicity of the aldehydes controls the course of the reaction.

  在水中，芳族/杂环醛与酮的合成上有用的吡咯烷催化的直接羟醛缩合反应以高达93％的产率提供了羟醛加成产物。醛的亲电性控制反应过程。
• Caesium carbonate functionalized magnetic nanoparticles: An efficient heterogeneous and reusable inorganic catalyst for aldol reaction in water
  作者：Nadia Fattahi、Muhammad Kashif、Ali Ramazani

  DOI：10.1016/j.inoche.2022.110388

  日期：2023.3

  efficiency of catalyst was investigated in the aldol reaction of acetone with various aldehydes in water. Utilization of simple and mild reaction conditions, short reaction time, green and safe solvent, catalyst with high catalytic performance and good recyclability, easy purification of the products and simple magnetically work-up, makes this approach as an interesting and effective option in the

  碳酸铯 (Cs 2 CO 3 ) 功能化 Fe 3 O 4 @SiO 2发现磁性纳米粒子是一种高效、磁可分离、可回收和绿色多相催化剂。X 射线粉末衍射 (XRD)、傅里叶变换红外 (FT-IR)、能量色散 X 射线光谱 (EDX)、扫描电子显微镜 (SEM)、透射电子显微镜 (TEM) 和振动样品磁强计 (VSM) ) 分析用于纳米催化剂的表征。在丙酮与各种醛在水中的羟醛反应中研究了催化剂的效率。由于反应条件简单温和、反应时间短、溶剂绿色安全、催化剂催化性能高、可回收性好、产物易于纯化、磁后处理简单，使该方法成为羟醛合成中一个有趣且有效的选择。反应。
• A useful synthetic equivalent of an acetone enolate
  作者：Veselin Maslak、Zorana Tokic-Vujosevic、Zorana Ferjancic、Radomir N. Saicic

  DOI：10.1016/j.tetlet.2009.09.113

  日期：2009.12

  2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers. (C) 2009 Elsevier Ltd. All rights reserved.
• Convenient enol equivalents for catalytic aldol-transfer reactions
  作者：Bixia Xi、Vesa Nevalainen

  DOI：10.1016/j.tetlet.2006.08.003

  日期：2006.10

  Solid crystalline and stable 1,1-diphenyl-1-hydroxy-3-butanone was shown to serve as an excellent precursor of the Al-enolate of acetone generated in situ for Al-BINOL catalyzed aldol-transfer reactions of aldehydes. The best yields were obtained with electron rich aromatic aldehydes and 2-pyridine carbaldehyde of which the latter gave 1-hydroxy-1-(2-pyridyl)-3-butanone in 79% yield. (c) 2006 Elsevier Ltd. All rights reserved.