4-hydroxy-4-(3',4',5'-trimethoxyphenyl)-butan-2-one | 208641-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-hydroxy-4-(3',4',5'-trimethoxyphenyl)-butan-2-one
• 英文别名: 4-hydroxy-4-(3',4',5'-trimethoxyphenyl)-2-butanone；4-hydroxy-4-(3,4,5-trimethoxyphenyl)butan-2-one；2-Butanone, 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-
• CAS: 208641-46-7
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: KDGXMZLPKSMTSC-UHFFFAOYSA-N

物化性质

• 熔点：
  60-63 °C
• 沸点：
  389.9±42.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二丙酮醇 、 3,4,5-三甲氧基苯甲醛 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83%的产率得到4-hydroxy-4-(3',4',5'-trimethoxyphenyl)-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

• Layered Double Hydroxides-Supported Diisopropylamide: Synthesis, Characterization and Application in Organic Reactions
  作者：M. Lakshmi Kantam、A. Ravindra、Ch. Venkat Reddy、B. Sreedhar、B. M. Choudary

  DOI：10.1002/adsc.200505266

  日期：2006.3

  The layered double hydroxides-supported diisopropylamide (LDH-DA) catalyst is found to be an efficient and selective solid base for aldol, Knoevenagel, Henry, Michael, transesterification and epoxidation reactions under liquid phase conditions. LDH-DA is synthesized by the interaction of lithium diisopropylamide with LDH-NO3 (as-synthesized) and calcined LDH-NO3. The LDH-DA (Mg/Al, 3/1) and their precursors

  发现层状双氢氧化物负载的二异丙基酰胺（LDH-DA）催化剂是在液相条件下用于醇醛，Knoevenagel，Henry，Michael，酯交换和环氧化反应的有效且选择性的固体碱。LDH-DA是通过二异丙基氨基锂与LDH-NO 3（合成后）和煅烧的LDH-NO 3相互作用而合成的。通过使用各种仪器技术，如FT-IR，TGA和DTA，粉末XRD，固态27 Al MAS NMR光谱，SEM和XPS（ESCA ），可以很好地表征LDH-DA（Mg / Al，3/1）及其前体）。
• 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。
• Asymmetric organocatalysis with glycosyl-β-amino acids: direct asymmetric aldol reaction of acetone with aldehydes
  作者：Namrata Dwivedi、Surendra S. Bisht、Rama P. Tripathi

  DOI：10.1016/j.carres.2006.08.007

  日期：2006.11

  Direct asymmetric aldol reaction of acetone with aromatic aldehydes was achieved in good yields and high enantioselectivity using 5-amino-5-deoxy-beta-L-ido-(alpha-D-gluco)-heptofuranuronic acids as a new class of organocatalysts.

  使用5-氨基-5-脱氧-β-L-氨基-（α-D-葡萄糖）-呋喃呋喃糖醛酸作为一类新型的有机催化剂，可实现丙酮与芳族醛的直接不对称醛醇缩合反应，并具有良好的收率和高对映选择性。
• Enhanced Effect of Mesoporous Silica on Base-Catalyzed Aldol Reaction
  作者：Yoshihiro Kubota、Kunio Goto、Shintaro Miyata、Yasutomo Goto、Yoshiaki Fukushima、Yoshihiro Sugi

  DOI：10.1246/cl.2003.234

  日期：2003.3

  Aldol reaction of 4-nitrobenzaldehyde with acetone gives 4-(4-nitrophenyl)-4-hydroxy-2-butanone in high yield in the presence of both secondary amine and mesoporous silica, whereas the yield is low in the absence of the mesoporous silica.

  在仲胺和介孔二氧化硅存在下，4-硝基苯甲醛与丙酮的羟醛反应以高产率生成4-(4-硝基苯基)-4-羟基-2-丁酮，而在不存在介孔二氧化硅的情况下，产率较低。
• Aldol condensations catalysed by novel Mg-Al-O-t-Bu hydrotalcite
  作者：B.M. Choudary、M. Lakshmi Kantam、B. Kavita、Ch. Venkat Reddy、K. Koteswara Rao、F. Figueras

  DOI：10.1016/s0040-4039(98)00547-4

  日期：1998.5

  A novel Mg-Al-O-t-Bu hydrotalcite prepared for the first time, catalyses condensation reactions selectively to aldols (3) at 0 degrees C in quantitative yields. (C) 1998 Elsevier Science Ltd. All rights reserved.