(S)-3-(naphth-2-yl)cyclohexanone | 250782-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3-(naphth-2-yl)cyclohexanone
• 英文别名: (S)-3-(2-naphthyl)cyclohexan-1-one；3-(2-naphtyl)cyclohexanone；3-(naphthalen-2-yl)cyclohexan-1-one；(S)-3-(naphthalen-2-yl)cyclohexan-1-one；(S)-3-(naphthalen-2-yl)cyclohexanone；(S)-3-(2-naphthyl)cyclohexanone；3-(2-naphthyl)cyclohexan-1-one；(3S)-3-(Naphthalen-2-yl)cyclohexan-1-one；(3S)-3-naphthalen-2-ylcyclohexan-1-one
• CAS: 250782-40-2
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: CJZGZPTYKOPUPG-AWEZNQCLSA-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)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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 、 2-萘硼酸 在 chlorobis(ethylene)rhodium(I) dimer 、 (R)-N-cinnamyl-t-butanesulfinamide 、 potassium phosphate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以99%的产率得到(S)-3-(naphth-2-yl)cyclohexanone
  参考文献：
  名称：

  N-肉桂氨磺酰胺作为不对称催化的新型含硫烯烃配体的 设计：通过明确的线性骨架实现结构简化†

  摘要：

  描述和设计了一种非常有趣的新型手性硫-烯烃杂化配体，该配体具有显着的结构简单性。这些独特的亚磺酰胺-烯烃配体已被证明是铑在芳基硼酸与α，β-不饱和羰基化合物的不对称1,4-加成反应中的高效配体（产率高达99％，ee高达98％）。

  DOI：

  10.1039/c2ob06723d

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 N-tert-butanesulfinyl α,β-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions
  作者：Xiangqing Feng、Beibei Wei、Jing Yang、Haifeng Du

  DOI：10.1039/c1ob05971h

  日期：——

  One novel type of chiral olefin/sulfinimide hybrid ligands has been developed through a simple one-step condensation of α,β-unsaturated ketones with tert-butanesulfinamide and utilized successfully for rhodium-catalyzed asymmetric conjugated additions to furnish the desired adducts in high yields with excellent ee's.

  通过α，β-不饱和酮与化合物的简单一步缩合，已经开发出一种新型的手性烯烃/亚磺酰亚胺杂化配体 叔丁烷亚磺酰胺 并成功地用于铑催化的不对称共轭加成中，从而以优异的ee高收率提供所需的加合物。
• 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）。
• 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。
• Chiral Phosphorus-Olefin Ligands for the Rh^I-Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron-Deficient Olefins
  作者：Qian Chen、Liang Li、Guangli Zhou、Xiaoli Ma、Lu Zhang、Fang Guo、Yi Luo、Wujiong Xia

  DOI：10.1002/asia.201600143

  日期：2016.5.20

  New chiral phosphorus–olefin hybrid ligands derived from the rigid “privileged” l‐proline have been conveniently prepared and applied in the rhodium‐catalyzed asymmetric arylation of electron‐deficient olefins with arylboronic acids at room temperature; this reaction provides the desired products in excellent yields and high enantioselectivities. The origin of observed stereoselectivity has been investigated

  衍生自刚性“特权” 1-脯氨酸的新型手性磷-烯烃杂化配体已在室温下方便地制备并应用于铑催化的缺电子烯烃与芳基硼酸的不对称芳基化反应。该反应以优异的产率和高对映选择性提供了所需的产物。观察到的立体选择性的起源已通过密度泛函理论（DFT）计算进行了研究。