3-(1-naphthyl)cyclopentanone | 213964-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-naphthyl)cyclopentanone
• 英文别名: 3-(naphthalen-1-yl)cyclopentan-1-one；(S)-3-(naphthalen-1-yl)cyclopentanone；(3S)-3-naphthalen-1-ylcyclopentan-1-one
• CAS: 213964-31-9
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: FSJUNEJWOCDYNG-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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-环戊烯酮 、 1-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3-(1-naphthyl)cyclopentanone
  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

• Fine‐Tuning the Bicyclo[3.3.1]nona‐2,6‐diene Ligands: Second Generation 4,8‐Substituted Dienes for Rh‐Catalyzed Asymmetric 1,4‐Addition Reactions
  作者：Vidmantas Bieliūnas、Sigitas Stončius

  DOI：10.1002/cctc.202100638

  日期：2021.9.7

  C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation

  设计和合成了第二代C 2 -对称 4,8-内，内 -双（烷氧基）双环 [3.3.1] 壬 - 2,6-二烯配体，具有额外的 4,8-外，外取代基。4,8- exo,exo基团通过加强 4,8-内、内侧链的构象刚性为配体结构的微调提供了进一步的元素。这种四取代的双环[3.3.1]壬二烯-2,6-二烯在铑催化的环烯酮与芳基硼酸的芳基化反应中被用作导向配体，提供相应的1,4-加成产物，产率良好至极好（69- 99 %) 和高达 99 % ee 的对映选择性。
• Efficient Pseudo-enantiomeric Carbohydrate Olefin Ligands
  作者：Holger Grugel、Fabian Albrecht、Tobias Minuth、Mike M. K. Boysen

  DOI：10.1021/ol3015896

  日期：2012.7.20

  pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral substrates. Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic

  由d-葡萄糖和d-半乳糖设计了高效的假对映体烯烃配体。这些配体在Rh（I）催化的芳基和烯基硼酸向非手性烯酮的1,4-加成反应中始终产生优异的对映选择性，并具有手性底物的高非对映选择性。与已建立的烯烃配体相反，它们是通过短合成法得到对映体纯的，没有外消旋拆分步骤，这使它们成为具有烯烃供体位点的手性配体的重要补充。
• Design of N-sulfinyl homoallylic amines as novel sulfinamide-olefin hybrid ligands for asymmetric catalysis: application in Rh-catalyzed enantioselective 1,4-additions
  作者：Shen-Shuang Jin、Hui Wang、Ming-Hua Xu

  DOI：10.1039/c1cc12322j

  日期：——

  Here we show that simple and readily available chiral sulfinamide-olefins can display great catalytic activities and enantioselectivities in rhodium-catalyzed 1,4-addition reactions. This study represent the first example of chiral sulfur-based olefin ligand class for transition metal-catalyzed asymmetric transformation.

  在此我们展示，简单易得的手性亚砜酰胺-烯烃在铑催化的1,4-加成反应中表现出极高的催化活性和对映选择性。这项研究代表了基于硫的手性烯烃配体类在过渡金属催化不对称转化中的首个实例。
• Design of N-cinnamyl sulfinamides as new sulfur-containing olefin ligands for asymmetric catalysis: achieving structural simplicity with a categorical linear framework
  作者：Shen-Shuang Jin、Hui Wang、Ting-Shun Zhu、Ming-Hua Xu

  DOI：10.1039/c2ob06723d

  日期：——

  The design and development of an extraordinarily interesting new class of chiral sulfur–olefin hybrid ligands with remarkable structural simplicity were described. These unique sulfinamide–olefin ligands have been proved to be highly effective ligands in rhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids to α,β-unsaturated carbonyl compounds (up to 99% yield and 98% ee).

  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％）。
• Convenient in situ generation of a chiral bis-N-heterocyclic carbene palladium catalyst and its application in enantioselective synthesis
  作者：Amrita B. Mullick、Matthew S. Jeletic、Andrew R. Powers、Ion Ghiviriga、Khalil A. Abboud、Adam S. Veige

  DOI：10.1016/j.poly.2012.07.046

  日期：2013.3

  To simplify catalytic reactions employing chelating bisNHC-metal complexes, studies were conducted to elucidate conditions for the in situ generation of a chiral chelating bisNHC-palladium catalyst from the corresponding diimidazolium salt. The method provides a convenient entry to catalytic reactions and eliminates catalyst preparation steps. In addition to the in situ prepared catalyst, for comparative purposes, isolable species were synthesized and characterized by NMR spectroscopy, combustion analysis, and single-crystal X-ray diffraction. Employing C-2-symmetric ligands derived from trans-9,10-Dihydro-9,10-EthanoAnthracene-11,12-diyl (DEA) and trans-9,10-Dihydro-9,10-EthanoAnthracene-11,12-diyl-Methanediyl (DEAM), diNHC-Pd complexes were synthesized and tested for activity in enantioselective arylboronic acid addition to cyclic enones. Published by Elsevier Ltd.