(3S)-3-(4-甲氧基苯基)-1-苯基戊-1-酮 | 142809-74-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: (3S)-3-(4-甲氧基苯基)-1-苯基戊-1-酮
• 英文名称: (+/-)-3-(4-methoxyphenyl)-1-phenyl-pentan-1-one
• 英文别名: (+/-)-3-(4-methoxyphenyl)-1-phenyl-1-pentanone；1-phenyl-3-(4-methoxyphenyl)lpentane-1-one；3-(4-methoxyphenyl)-1-phenylpentan-1-one；3-(4-methoxy-phenyl)-1-phenyl-pentan-1-one；3-(4-Methoxy-phenyl)-1-phenyl-pentan-1-on
• CAS: 142809-74-3；142809-75-4；138982-98-6
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: QGPHPSGZFOOFBW-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  406.7±38.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-3-(4-甲氧基苯基)-1-苯基戊-1-酮 以 苯 为溶剂， 生成 (1R,2R,3R)-3-(4-Methoxy-phenyl)-2-methyl-1-phenyl-cyclobutanol 、 (1R,2S,3R)-3-(4-Methoxy-phenyl)-2-methyl-1-phenyl-cyclobutanol
  参考文献：
  名称：

  β-茴香基链烷酮的Norrish II型光反应性和溶剂对立体选择性Yang环化的影响

  摘要：

  与一般认为β-芳基苯乙酮具有光稳定性的观点相反，发现β-茴香基酮1和2的光解会导致Norrish II型反应；杨环化以高度立体选择性的方式以中等收率（31-43％）提供了两种环丁醇。发现溶剂对环丁醇的相对比例具有显着影响，因为在非极性溶剂（例如苯）中的主要产物在极性溶剂（例如乙腈或甲醇）中变为次要产物。

  DOI：

  10.1016/s0040-4039(03)00318-6
• 作为产物：
  描述：

  乙基溴化镁 、 4-甲氧基查耳酮 在 乙醚 作用下， 生成 (3S)-3-(4-甲氧基苯基)-1-苯基戊-1-酮
  参考文献：
  名称：

  Kohler, American Chemical Journal, 1907, vol. 38, p. 559

  摘要：

  DOI：

文献信息

• Chiral Phosphanylferrocenecarboxamides with Amino Acid Pendant Groups as Ligands for Cu-Mediated Asymmetric Conjugate Additions of Diethylzinc to Chalcones - Structural Characterisation of Precursors to the Cu Catalyst
  作者：Jiří Tauchman、Ivana Císařová、Petr Štěpnička

  DOI：10.1002/ejoc.201000480

  日期：2010.8

  A series of chiral phosphanylferrocenecarboxamides was prepared by treatment of either 1'-(diphenylphosphanyl)-ferrocene-1-carboxylic acid (Hdpf) or its planar-chiral 1,2-isomers with amino acid methyl esters in the presence of peptide coupling agents. The compounds were characterised by spectroscopic methods, and the crystal structure of one representative was determined by X-ray diffraction. Catalytic

  在肽偶联剂的存在下，通过用氨基酸甲酯处理 1'-(二苯基膦酰基)-二茂铁-1-羧酸 (Hdpf) 或其平面手性 1,2-异构体制备了一系列手性 phosphanylferrocenecarboxamides。通过光谱方法对化合物进行表征，并通过 X 射线衍射确定了一个代表的晶体结构。这些供体在铜催化的二乙基锌与查耳酮的不对称共轭加成反应中的催化测试表明，反应结果对配体结构和反应条件（铜源和溶剂）高度敏感，而查耳酮取代基（Me、MeO 或 Cl在位置 4 或 4') 的影响不那么明显。基于 Hdpf 的化合物被证明是比它们的平面手性类似物更好的配体。在优化条件下，与 L-缬氨酸-Hdpf 共轭物、(S)-Ph 2 PfcCONHCH(CHMe 2 )-CO 2 Me (fc = 二茂铁-1,1'-二基) 和未取代的查耳酮反应得到完全转化率 (20 °C/ 4 h) 和 87 % ee。氨基膦
• Highly Enantioselective Conjugate Addition of Diethylzinc to Acyclic Enones with Fine-Tunable Phosphite−Pyridine Ligands
  作者：Huihui Wan、Yuanchun Hu、Yuxue Liang、Shuang Gao、Junwei Wang、Zhuo Zheng、Xinquan Hu

  DOI：10.1021/jo0345897

  日期：2003.10.1

  and (S)-2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-1,1'-biphenyl was employed in Cu(I)-catalyzed conjugate addition of diethylzinc to acyclic enones. Excellent enantioselectivities (up to 98% ee) and highly catalytic activities were achieved for a variety of acyclic enones.

  由（S）-2-氨基-2'-羟基-6,6'-二甲基-1,1'-联苯和（S）-2衍生的一系列新的亚磷酸酯-吡啶微调（P，N）配体-氨基-2'-羟基-4,4'，6,6'-四甲基-1,1'-联苯用于二乙基锌与无环烯酮的Cu（I）催化共轭加成反应。各种无环烯酮均具有出色的对映选择性（高达98％ee）和高度催化活性。
• Design and synthesis of new chiral pyridine–phosphite ligands for the copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones
  作者：Yinjun Xie、Hanmin Huang、Weimin Mo、Xiangqun Fan、Zhiqiang Shen、Zhenlu Shen、Nan Sun、Baoxiang Hu、Xinquan Hu

  DOI：10.1016/j.tetasy.2009.05.014

  日期：2009.7

  A series of new chiral pyridine-phosphite ligands have been prepared from (R)-pyridyl alcohols and BINOL-derived chlorophosphite, and successfully employed in the copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones. Using the simple and inexpensive CuBr2 as a precursor, the enantioselective additions to various Substituted acyclic enones afforded products in high yields and good enantioselectivities (up to 92% ee). (C) 2009 Elsevier Ltd. All rights reserved.
• US6380392B1
  申请人：——

  公开号：US6380392B1

  公开（公告）日：2002-04-30
• [EN] LIGANDS BASED ON CHIRAL 2-AMINO-2'-HYDROXY-1,1'-BINAPHTHYL AND RELATED FRAMEWORKS FOR ASYMMETRIC CATALYSIS<br/>[FR] LIGANDS ETABLIS SUR LA BASE DE 2-AMINO-2'-HYDROXY-1,1'-BINAPHTYLE CHIRAL ET EDIFICES CONNEXES POUR CATALYSE ASYMETRIQUE
  申请人：PENN STATE RES FOUND

  公开号：WO2001000581A1

  公开（公告）日：2001-01-04

  The present invention includes array of new chiral ligands that are optically active or racemic. These ligands are bidentate, tridentate, tetradentate or pentadentate ligands which include P-P, P-N, N-N, mixed P-N, Schiff base or carbene sites. The present invention further includes a catalyst prepared by a process, which includes contacting a transition metal salt, or a complex thereof, and a ligand according to the present invention. The present invention still further includes a process for preparation of an asymmetric compound. In this process, a substrate capable of forming an asymmetric product by an asymmetric reaction and a catalyst according to the present invention are contacted to produce an asymmetric product. Transition metal complexes with these ligands are effective catalysts for asymmetric reactions. Applicant has discovered that asymmetric products can be prepared using the chiral catalysts according to the present invention in enantioselective reactions, such as hydrogenation, hydroformylation, Michael addition, Heck reaction, Aldol reaction, allylic alkylation, cyclopropanation, epoxidation, and olefin metathesis.