(3S)-3-(2-甲氧基苯基)环戊烷-1-酮 | 155325-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (3S)-3-(2-甲氧基苯基)环戊烷-1-酮
• 英文名称: 3-(2-methoxyphenyl)cyclopentanone
• 英文别名: (3S)-3-(2-Methoxyphenyl)cyclopentan-1-one
• CAS: 155325-48-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: MOUCCUJQVSNBQT-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-Methoxyphenylmagnesium bromide 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 bis{(S,S-chiraphos)rhodium(I)}perchlorate 、 酒石酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 87.0h， 生成 (3S)-3-(2-甲氧基苯基)环戊烷-1-酮
  参考文献：
  名称：

  不对称催化。使用手性二膦铑催化剂对 4-戊烯醛进行不对称催化分子内加氢酰化

  摘要：

  [Rh(手性二膦)] + 类型的催化剂在 25 o C 下将 4-取代的 4-戊烯醛转化为相应的 3-取代的环戊酮，其转换数和频率通常很高。 具有两个手性二膦的各种取代的 4-戊烯醛的对映选择性已被探索。发现使用 binap 催化剂，对于带有 4-取代叔取代基的 4-戊烯醛底物和酯基，观察到几乎完全的对映选择性。酮取代基具有非常高的对映选择性

  DOI：

  10.1021/ja00084a025

文献信息

• Design and Synthesis of Polymeric Chiral Bicyclo[3.3.0] Diene as Reusable Ligand for Rhodium-Catalyzed Asymmetric 1,4-Addition
  作者：Hongyu Yang、Minghua Xu

  DOI：10.1002/cjoc.201201079

  日期：2013.1

  A series of A‐B type sterically regular bicyclio[3.3.0] diene‐based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh‐catalyzed asymmetric 1,4‐addition of arylboronic acids to α,β‐unsaturated ketones.

  设计并合成了一系列基于A‐B型空间正则双环[3.3.0]二烯的聚合物，作为固定的手性二烯配体进行不对称催化。使用聚合二烯6b，可以在Rh催化的芳基硼酸的不对称1,4-加成反应中获得出色的对映选择性，对α，β-不饱和酮。
• 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。
• 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.
• 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.