(S)-3-(4-methoxylphenyl)cyclohexanone | 250782-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-(4-methoxylphenyl)cyclohexanone
• 英文别名: (S)-3-(4-methoxyphenyl)cyclohexanone；(-)-3-(4-methoxyphenyl)cyclohexan-1-one；3-(4-methoxyphenyl)cyclohexanone；(3S)-3-(4-methoxyphenyl)cyclohexan-1-one
• CAS: 250782-40-2
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: VEETYWFTVNETTL-NSHDSACASA-N

物化性质

• 沸点：
  335.7±42.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-4'-methoxy-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one 在 palladium on activated charcoal 氢气 作用下， 生成 (S)-3-(4-methoxylphenyl)cyclohexanone
  参考文献：
  名称：

  活化烯酮的不对称镍催化共轭烯丙基化

  摘要：

  描述了镍催化的烯丙基硼酸频哪醇酯烯丙基 B(pin) 的对映选择性加成。该反应对二亚烷基酮非常有效，并有利于非对称底物中亚苄基位点的烯丙基化。该反应似乎是通过将二亚烷基酮底物转化为不饱和的 pi-烯丙基络合物 (I)，然后进行还原消除来进行的。当使用手性配体 14 时，一系列底物的对映选择性范围为 91% 至 94% ee。

  DOI：

  10.1021/ja710922h

文献信息

• Readily Accessible Chiral Diene Ligands for Rh-Catalyzed Enantioselective Conjugate Additions of Boronic Acids
  作者：Barry M. Trost、Aaron C. Burns、Thomas Tautz

  DOI：10.1021/ol201754c

  日期：2011.9.2

  the broad scope of the Pd-catalyzed asymmetric alkylation of meso- and d,l-divinylethylene carbonate, several chiral diene ligands were prepared in two steps from commercial materials. Subsequently, these ligands were evaluated in the Rh-catalyzed asymmetric conjugate addition of boronic acids to enones.

  由于Pd催化的内消旋和d，1-二乙烯基碳酸亚乙酯的不对称烷基化反应的广泛范围，从商业原料中分两步制备了几种手性二烯配体。随后，在硼酸到烯酮的Rh催化的不对称共轭加成中评估了这些配体。
• Chiral porous organic frameworks for asymmetric heterogeneous catalysis and gas chromatographic separation
  作者：Jinqiao Dong、Yan Liu、Yong Cui

  DOI：10.1039/c4cc07648f

  日期：——

  Three chiral robust diene-based porous organic frameworks (POFs) are prepared. POF-1 is shown to be an efficient heterogeneous catalyst after metallation for asymmetric conjugation addition with up to 93% ee, and it can also function as a new chiral stationary phase for gas chromatographic separation of racemates.

  制备了三种具有手性的稳定二烯基多孔有机框架（POFs）。实验表明，POF-1经过金属化后，作为一种高效的非均相催化剂，用于不对称共轭加成时，其对映体过量率可达93%，同时它还可以作为新型的手性固定相，用于气相色谱法拆分外消旋混合物。
• Chiral Sulfoxide-Olefin Ligands: Completely Switchable Stereoselectivity in Rhodium-Catalyzed Asymmetric Conjugate Additions
  作者：Guihua Chen、Jiangyang Gui、Liangchun Li、Jian Liao

  DOI：10.1002/anie.201102586

  日期：2011.8.8

  it both ways: A novel class of chiral sulfoxide‐olefin ligands was synthesized from a single chiral source. These ligands were evaluated in rhodium‐catalyzed 1,4‐additions of arylboronic acids to electron‐deficient olefins, and remarkable olefin‐directed reversal of stereoselectivity (up to >99 % ee, R isomer; 98 % ee, S isomer) was observed when the reversal ligand pair L1 (branched olefin) and L2

  两者兼有：从单一手性来源合成了一类新型的手性亚砜-烯烃配体。在铑催化的芳基硼酸的1,4加成反应中，对这些配体进行了评估，并观察到电子不足的烯烃，并 观察到烯烃定向的立体选择性显着逆转（高达99％ee，R 异构体； 98％ee，S异构体）。当使用反向配体对L1（支链烯烃）和L2（直链烯烃）时（参见方案）。
• Highly Practical Catalytic Asymmetric 1,4-Addition of Arylboronic Acids in Water Using New Hydrophilic Chiral Bicyclo[3.3.0] Diene Ligands
  作者：Chen-Guo Feng、Zhi-Qian Wang、Cheng Shao、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1021/ol801665z

  日期：2008.9.18

  The first Rh-diene-catalyzed aqueous asymmetric 1,4-addition of alpha,beta-unsaturated carbonyl compounds with arylboronic acids has been realized. By using a hydrophilic bicyclo[3.3.0] diene ligand, the reactions can be performed successfully in neat water at room temperature to afford the corresponding products in good yields and with very high enantioselectivities for both cyclic and linear substrates

  已经实现了第一Rh-二烯催化的α，β-不饱和羰基化合物与芳基硼酸的不对称1，4-加成水溶液。通过使用亲水性双环[3.3.0]二烯配体，可以在室温下于纯水中成功地进行反应，从而以高收率和对环和线性底物都具有非常高的对映选择性提供相应的产物。
• A chiral phosphine–olefin ligand derived from l-hydroxyproline and its use in the rhodium-catalyzed asymmetric 1,4-addition
  作者：Vasudeva Rao Gandi、Yixin Lu、Tamio Hayashi

  DOI：10.1016/j.tetasy.2015.05.004

  日期：2015.7

  A new chiral phosphine–olefin ligand (S)-1 has been designed and synthesized from l-hydroxyproline via a short reaction sequence. It was examined for its efficiency in the rhodium-catalyzed asymmetric addition of arylboronic acids and a phenylzinc reagent to cyclic α,β-unsaturated ketones, giving 1,4-addition products with high enantioselectivities.

  一种新的手性膦配体的烯烃（小号） - 1已被设计，并通过短的反应序列从L-羟脯氨酸合成。它检查其在铑催化的不对称加成的芳基硼酸的效率和phenylzinc试剂环状α，β不饱和酮，得到1,4-加成产品具有高对映选择性。