(3S)-3-(2-fluorophenyl)cyclohexanone

• 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: (3S)-3-(2-fluorophenyl)cyclohexanone
• 英文别名: (S)-3-(2-fluorophenyl)-cyclohexanone；3-(2-fluorophenyl)cyclohexanone；(S)-3-(2-fluorophenyl)cyclohexan-1-one；(3S)-3-(2-fluorophenyl)cyclohexan-1-one
• 化学式: C₁₂H₁₃FO
• 分子量: 192.233
• InChiKey: GWFDDEVKTLLHSH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 2-氟苯硼酸 在 Rh(H2C=CH2)2Cl 氢氧化钾 、 R,R,R-5-All-3-iBu-8-MeO-1,8-Me₂bicyclo[2.2.2]octa-2,5-diene 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以94%的产率得到(3S)-3-(2-fluorophenyl)cyclohexanone
  参考文献：
  名称：

  手性[2.2.2]二烯作为Rh（I）的配体，是硼酸向各种受体的共轭加成。

  摘要：

  [反应：见正文]我们记录了一系列研究，这些研究导致了新的取代的[2.2.2]-二烯配体，在Rh（I）催化的共轭加成反应中，对先前未用二烯配体检查的底物表现出高选择性。此外，我们公开了由于在配体支架上引入了第三个C = C而产生的出乎意料的有趣效果（参见1）。

  DOI：

  10.1021/ol048240x

文献信息

• Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors
  作者：Christian Defieber、Jean-François Paquin、Sonia Serna、Erick M. Carreira

  DOI：10.1021/ol048240x

  日期：2004.10.1

  [reaction: see text] We document a series of investigations that led to new substituted [2.2.2]-diene ligands which display high selectivity in Rh(I)-catalyzed conjugate addition reactions to substrates not previously examined with diene ligands. Moreover, we disclose an unexpected, interesting effect that results from the introduction of a third C=C onto the ligand scaffold (cf. 1).

  [反应：见正文]我们记录了一系列研究，这些研究导致了新的取代的[2.2.2]-二烯配体，在Rh（I）催化的共轭加成反应中，对先前未用二烯配体检查的底物表现出高选择性。此外，我们公开了由于在配体支架上引入了第三个C = C而产生的出乎意料的有趣效果（参见1）。
• α,β-Divinyl Tetrahydropyrroles as Chiral Chain Diene Ligands in Rhodium(I)-Catalyzed Enantioselective Conjugated Additions
  作者：Qian Li、Zhe Dong、Zhi-Xiang Yu

  DOI：10.1021/ol103152t

  日期：2011.3.4

  A series of α,β-divinyl tetrahydropyrroles, synthesized by asymmetric allylic C−H bond activation/conjugated diene addition reaction of ene-2-dienes, were found to be very efficient chiral chain diene ligands in the rhodium-catalyzed conjugated addition of organoboronic acids to various α,β-unsaturated compounds, achieving the desired chiral adducts with good to excellent yields and ee values.

  通过烯-2-二烯的不对称烯丙基CH键活化/共轭二烯加成反应合成的一系列α，β-二乙烯基四氢吡咯在铑催化的有机硼的共轭加成中是非常有效的手性链二烯配体酸生成各种α，β-不饱和化合物，从而以所需的良好收率和ee值获得所需的手性加合物。
• High Efficiency and Enantioselectivity in the Rh-Catalyzed Conjugate Addition of Arylboronic Acids Using Monodentate Phosphoramidites
  作者：Jean-Guy Boiteau、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/jo035155e

  日期：2003.11.1

  A very fast reaction and enantioselectivities >98% have been reached in the rhodium-catalyzed arylboronic acid addition to enones using a monodentate phosphoramidite ligand. Temperature-dependent studies show that monodentate phosphoramidites form stable complexes with metals and can induce high enantioselectivities even at high temperatures in polar solvents.

  使用单齿亚磷酰胺配体，在铑催化的芳基硼酸与烯酮的加成中，已经实现了非常快的反应和对映选择性> 98％。依赖温度的研究表明，单齿亚磷酰胺与金属形成稳定的络合物，即使在极性溶剂中即使在高温下也可以诱导高对映选择性。
• A Class of Benzene Backbone-Based Olefin–Sulfoxide Ligands for Rh-Catalyzed Enantioselective Addition of Arylboronic Acids to Enones
  作者：Feng Xue、Xincheng Li、Boshun Wan

  DOI：10.1021/jo2011472

  日期：2011.9.2

  A class of readily available and easily tunable benzene backbone-based olefin–sulfoxide ligands was developed for the rhodium-catalyzed asymmetric conjugate addition reaction of arylboronic acids to enones with up to 97% yield and 97% ee.

  针对铑催化的芳基硼酸与烯酮的不对称共轭加成反应，开发了一种易于获得且易于调节的基于苯骨架的烯烃-亚砜配体，产率高达97％，ee高达97％。
• Sulfoxide–Alkene Hybrids: A New Class of Chiral Ligands for the Hayashi–Miyaura Reaction
  作者：Tobias Thaler、Li-Na Guo、Andreas K. Steib、Mihai Raducan、Konstantin Karaghiosoff、Peter Mayer、Paul Knochel

  DOI：10.1021/ol200841x

  日期：2011.6.17

  Sulfoxide-alkene hybrids are introduced as a new class of chiral heterodentate ligands for the Hayashi-Miyaura reaction. The synthesis of these ligands was achieved without the use of protecting groups. A chiral resolution was performed via simple column-chromatographic separation of the diastereomeric ligands. Both diastereomers proved to be excellent ligands In Rh-catalyzed 1,4-addition reactions, furnishing chiral Products with high enantloselectivities and, remarkably, opposite stereoconfigurations.