3-hydroxy-1,4-diphenyl-butan-1-one | 54322-84-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-hydroxy-1,4-diphenyl-butan-1-one
• 英文别名: 1,4-diphenyl-3-hydroxy-1-butanone；3-hydroxy-1,4-diphenylbutan-1-one；3-Hydroxy-1,4-diphenyl-1-butanone
• CAS: 54322-84-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: ACOOYQMOKLIVJM-UHFFFAOYSA-N

物化性质

• 熔点：
  85.0-86.0 °C
• 沸点：
  418.7±38.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1,4-diphenyl-butan-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 以93%的产率得到(3E)-1,4-diphenylbut-3-en-1-one
  参考文献：
  名称：

  Hantawong, Kesra; Murphy, William S., Journal of Chemical Research, Miniprint, 1988, # 10, p. 2520 - 2547

  摘要：

  DOI：
• 作为产物：
  描述：

  5-benzyl-3-phenyl-4,5-dihydroisoxazole 在 氢气 、 镍 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以28%的产率得到3-hydroxy-1,4-diphenyl-butan-1-one
  参考文献：
  名称：

  Synthesis and Evaluation of Estrogen Agonism of Diaryl 4,5-Dihydroisoxazoles, 3-Hydroxyketones, 3-Methoxyketones, and 1,3-Diketones: A Compound Set Forming a 4D Molecular Library

  摘要：

  In this paper, the preparation and systematic evaluation of estrogen receptor alpha (ER alpha) and estrogen receptor beta (ER beta) activities of some diaryl-1,3-diones and their synthetic intermediates, diaryl-4,5-dihydroisoxazoles, diaryl-3-hydroxyketones, diaryl-3-methoxyketones, and diaryl-2-(dimethyl-lambda(4)-sulfanylidene)-1,3-diones, is described. The set of 72 compounds constitutes a general schematic structure aryl1-linker1-spacer-linker2-aryl2, where the linker1-spacer-linker2 length varies between 4 and 8 carbons. The set of compounds was applied here to map and explore the active sites of subtypes ER alpha and ER beta. The highest activities were obtained with dihydroisoxazole and hydroxyketone spacers, but even the most flexible diones with unsubstituted aryl groups showed some agonism. Most compounds were found to be ER alpha selective or to activate both receptors, but in some cases we saw also clearly stronger ER beta activation.

  DOI：

  10.1021/jm8001795

文献信息

• Intramolecular O−H···O Hydrogen-Bond-Mediated Reversal in the Partitioning of Conformationally Restricted Triplet 1,4-Biradicals and Amplification of Diastereodifferentiation in Their Lifetimes
  作者：Jarugu Narasimha Moorthy、Subhas Samanta、Apurba L. Koner、Satyajit Saha、Werner M. Nau

  DOI：10.1021/ja8032179

  日期：2008.10.15

  reverse their partitioning between cyclization and elimination compared with the behavior of the biradicals of ketones 3; the ketones 8-anti and 9-anti underwent cyclization in benzene, predominantly leading to cyclobutanols with syn stereochemistry between the C2 and C3 substituents. In accordance with photoproduct profiles, an unprecedented approximately 2-fold difference in the lifetimes of the intermediate

  已经研究了一组合理设计的酮 4-9 的光反应性和纳秒瞬态现象，以全面了解分子内氢键对 (i) 三线态 1,4-双自由基的寿命和 (ii)后者在环化和消除之间的分配。酮 6 与 8 和 7 与 9 的双自由基的光化学结果和寿命数据的比较揭示了当叠加在空间因素上时氢键的显着影响：虽然 6 和 7 产生的环丁醇收率很低，但发现环化占主导地位8-anti 和 9-anti 中等，在环丁醇的形成中具有高立体选择性（8-anti > 95%）。在 8 的情况下，非对映化学几乎完全允许发生断裂或环化（8-抗环化>90%，8-syn 消除>75%）。值得注意的是，与酮 3 的双自由基的行为相比，8 和 9 的双自由基中的分子内氢键逆转了它们在环化和消除之间的分配；酮 8-anti 和 9-anti 在苯中进行环化，主要导致在 C2 和 C3 取代基之间具有顺式立体化学的环丁醇。根据光产物曲线，酮 8 的中
• Neodymium(III)-Mediated Reformatsky-Type Reactions of α-Halo Ketones with Carbonyl Compounds
  作者：Stefan F. Kirsch、Clémence Liébert

  DOI：10.1002/ejoc.200700240

  日期：2007.8

  In a neodymium(III) iodide induced process, α-bromo ketones 1 and aldehydes 2 are effectively converted into aldol products 3. This Reformatsky-type reaction proceeds through the formation of a neodymium enolate at room temperature in CH2Cl2. The analogous reaction in the presence of NdBr3/NaI at 50 °C in THF favors the formation of corresponding aldol–Tishchenko products 5 in good yields. Studies

  在碘化钕 (III) 诱导的过程中，α-溴酮 1 和醛 2 有效地转化为醛醇产物 3。该 Reformatsky 型反应通过在室温下在 CH2Cl2 中形成烯醇钕来进行。在 NdBr3/NaI 存在下，在 50 °C THF 中的类似反应有利于以良好的产率形成相应的 aldol-Tishchenko 产物 5。还描述了定义由钕 (III) 盐介导的这些反应的范围和局限性的研究。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007）
• FeCl₃·6H₂O-Catalyzed Mukaiyama-Aldol Type Reactions of Enolizable Aldehydes and Acetals
  作者：Alejandra Rodríguez-Gimeno、Ana B. Cuenca、Jesús Gil-Tomás、Mercedes Medio-Simón、Andrea Olmos、Gregorio Asensio

  DOI：10.1021/jo501498a

  日期：2014.9.5

  stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air

  衍生自可烯化醛的缩醛的Mukaiyama-aldol型缩醛与环保，低成本且稳定的催化剂FeCl 3 ·6H 2 O生成的β-甲氧基羰基化合物的收率接近定量。该方法已扩展到母体醛作为起始原料，从而导致相应的醛醇缩合物的收率较低，但效率很高。在与直链和环状甲硅烷基烯醇醚的反应中，已经测试了不同的烷基和芳基取代的缩醛和醛。反应在露天气氛中进行，不需要添加剂。在这种类型的FeCl 3 ·6H 2 O催化的缩合反应中，缩醛可以被认为是羰基部分的活化基团，而不是保护基团。
• Synthesis of 1,3-Dicarbonyl Compounds by the Oxidation of 3-Hydroxycarbonyl Compounds with Corey-Kim Reagent
  作者：Sadamu Katayama、Kinue Fukuda、Toshio Watanabe、Masashige Yamauchi

  DOI：10.1055/s-1988-27506

  日期：——

  A new method for the preparation of various 1,3-dicarbonyl compounds is described. Oxidation of 3-hydroxycarbonyl compounds without substituent at C-2 position by the Corey-Kim reagent (N-chlorosuccinimide-dimethyl sulfide) afforded the stable dimethylsulfonium methylides, which on reductive desulfurization by zinc-acetic acid furnished the 1,3-dicarbonyl derivatives.On the other hand, the same treatment of 2-mono-, or 2,2-disubstituted 3-hydroxy-carbonyl compounds gave directly the corresponding 1,3-dicarbonyl analogous,respectively.

  描述了一种制备各种1,3-二酮化合物的新方法。对C-2位置没有取代基的3-羟基酮化合物进行氧化，使用Corey-Kim试剂（N-氯琥珀酰亚胺-二甲基硫化物）得到了稳定的二甲基硫鎓甲基化合物，而这些化合物在锌-醋酸的还原脱硫作用下，生成了1,3-二酮衍生物。另一方面，对2-单取代或2,2-二取代的3-羟基酮化合物进行相同处理，分别直接获得了相应的1,3-二酮类化合物。
• One-Pot Reduction-Aldol Reaction of Esters
  作者：Andrei K. Yudin、Mikio Sasaki

  DOI：10.1055/s-2004-834808

  日期：——

  We have developed a new protocol for making aldol adducts in a one-pot reaction between esters and silyl enol ethers in the presence of DIBALH without isolating the intermediate aldehydes. Lewis acid activation of the initially formed aluminated hemiacetals produces highly reactive electrophilic aldehyde equivalents in situ. Using this protocol, various aldol adducts can be readily obtained in up to 90% yield on a large scale.

  我们开发了一种新的协议，通过在DIBALH的存在下，在酯和硅烯醇醚之间进行一锅反应来合成醇缩合加合物，而无需分离中间体醛。最初形成的铝修饰半缩醛经过路易斯酸激活，产生高反应性的电亲体醛等效物。采用此协议，可以在大规模上实现多种醇缩合加合物，产率高达90%。