(S)-3-(4-chlorophenyl)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: (S)-3-(4-chlorophenyl)cyclohexanone
• 英文别名: 3-(4-chlorophenyl)cyclohexanone；(3S)-3-(4-chlorophenyl)cyclohexan-1-one
• 化学式: C₁₂H₁₃ClO
• 分子量: 208.688
• InChiKey: GOIKJBFDOSEDRS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 4-氯苯硼酸 在 acetylacetonatobis(ethylene)rhodium(I) 、 (R)-BICMAP 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以31%的产率得到(S)-3-(4-chlorophenyl)cyclohexanone
  参考文献：
  名称：

  手性二氢苯并呋喃基二膦（BICMAP）：光学拆分及其在铑（I）催化的芳基和烯基硼酸向环烯酮的不对称1,4-加成反应中的应用

  摘要：

  基于手性二氢苯并呋喃的二膦配体（BICMAP）1用作铑（I）催化的芳基硼酸不对称1,4-加成至环烯酮（ee高达99％ee）的配体。我们还发现，BICMAP-铑体系是一种有效的催化剂，用于以良好的对映选择性将烯基硼酸1，4-加成至2-环己烯酮。

  DOI：

  10.1016/j.tetlet.2012.06.064

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）。
• Chiral dihydrobenzofuran-based diphosphine (BICMAP): optical resolution and application to rhodium(I)-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to cyclic enones
  作者：Takashi Mino、Masatoshi Hashimoto、Katsunori Uehara、Yoshiaki Naruse、Shohei Kobayashi、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetlet.2012.06.064

  日期：2012.8

  Chiral dihydrobenzofuran-based diphosphine ligand (BICMAP) 1 was used as a ligand for the rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to cyclic enones up to 99% ee. We also found that the BICMAP-rhodium system was an efficient catalyst for the 1,4-addition of alkenylboronic acids to 2-cyclohexenone in good enantioselectivities.

  基于手性二氢苯并呋喃的二膦配体（BICMAP）1用作铑（I）催化的芳基硼酸不对称1,4-加成至环烯酮（ee高达99％ee）的配体。我们还发现，BICMAP-铑体系是一种有效的催化剂，用于以良好的对映选择性将烯基硼酸1，4-加成至2-环己烯酮。
• Application of chiral N-tert-butylsulfinyl vinyl aziridines in Rh(i) catalyzed 1,4-addition of aryl boronic acids to cyclic enones
  作者：Qian Chen、Chao Chen、Fang Guo、Wujiong Xia

  DOI：10.1039/c3cc42673d

  日期：——

  Chiral N-tert-butylsulfinyl vinyl aziridine ligands prepared from a readily available (R)-tert-butanesulfinamide have been applied in the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones, which gives high yields and excellent enantioselectivities.

  由易于获得的（R）-叔丁烷亚磺酰胺制备的手性N-叔丁基亚磺酰基乙烯基氮丙啶配体已用于铑催化的芳基硼酸与环烯酮的1,4-不对称加成反应，可提供高收率和出色的对映选择性。