(-)-(S)-2-phenylcyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(S)-2-phenylcyclopentanone
• 英文别名: 2-phenylcyclopentanone；(2S)-2-phenylcyclopentan-1-one
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: NPELEPAOYMNNRW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (+)-L_g-tartaric acid amide-(2-phenyl-cyclopentylidenehydrazide) 在 盐酸 、 Petroleum ether 作用下， 生成 (-)-(S)-2-phenylcyclopentanone
  参考文献：
  名称：

  The Effect of Ring Formation on Optical Rotatory Power. A Comparison of the Optical Rotations of 2-Phenylcyclopentanone and of Some Acyclic α-Phenyl Ketones

  摘要：

  DOI：

  10.1021/ja01611a056

文献信息

• Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
  作者：Michael R. Harris、Mikhail O. Konev、Elizabeth R. Jarvo

  DOI：10.1021/ja5026485

  日期：2014.6.4

  Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both π-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective

  对映体富集的亚甲基环戊烷是通过二级苄基醚的立体有择、镍催化的 Heck 环化反应合成的。对于 π 扩展和简单芳烃的苄醚，该反应以高产率和对映特异性进行。带有侧链 1,2-二取代烯烃的醚形成三取代烯烃，同时控制绝对构型和烯烃几何形状。证明了多环呋喃的非对映选择性合成。
• Highly Efficient and Enantioselective α-Arylation of Cycloalkanones by Scandium-Catalyzed Diazoalkane-Carbonyl Homologation
  作者：Jason Kingsbury、Victor Rendina、Hilan Kaplan

  DOI：10.1055/s-0031-1289650

  日期：2012.3

  Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazo­alkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98:2 er and >98% yield. The formal C-C insertion of aryldiazo­methanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of α-arylation.

  功能化的α-叔和α-季2-芳基环烷酮通过三氟甲磺酸钪(III)催化的重氮甲烷-羰基同系化反应迅速获得。最近的进展使得碳插入反应能够在催化剂负载量低至0.5 mol%的情况下进行，规模可达5 mmol。结合易于获得的基于双和三噁唑啉的配体与三氟甲磺酸钪，可以合成具有高达98:2 对映体比和>98%产率的芳基化中环碳环。芳基重氮甲烷在无取代环烷酮中的正式C-C插入提供了一种一步解决α-芳基化持续挑战的方法。
• An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion
  作者：Victor L. Rendina、David C. Moebius、Jason S. Kingsbury

  DOI：10.1021/ol200402m

  日期：2011.4.15

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.
• Enantioselective Synthesis of 2-Aryl Cyclopentanones by Asymmetric Epoxidation and Epoxide Rearrangement
  作者：Yu-Mei Shen、Bin Wang、Yian Shi

  DOI：10.1002/anie.200501520

  日期：2006.2.20
• The Effect of Ring Formation on Optical Rotatory Power. A Comparison of the Optical Rotations of 2-Phenylcyclopentanone and of Some Acyclic α-Phenyl Ketones
  作者：Kurt Mislow、Charles L. Hamermesh

  DOI：10.1021/ja01611a056

  日期：1955.3