(S)-(+)-3-cyclohexyl-1-phenyl-1-pentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-3-cyclohexyl-1-phenyl-1-pentanone
• 英文别名: (S)-(-)-3-cyclohexyl-1-phenylpentan-1-one；(S)-3-cyclohexyl-1-phenylpentan-1-one；(3S)-3-cyclohexyl-1-phenyl-pentanone；3-cyclohexyl-1-phenylpentan-1-one；(3S)-3-cyclohexyl-1-phenylpentan-1-one
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: CYWNSLPKDFNIMJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  苯乙酮 在 bis(acetylacetonate)nickel(II) 、 sodium hydroxide 、 chiral ferrocene-based reagent 作用下， 以 乙醇 、 正己烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-(+)-3-cyclohexyl-1-phenyl-1-pentanone
  参考文献：
  名称：

  Application of ferrocenyl substituted aziridinylmethanols (FAM) as chiral ligands in enantioselective conjugate addition of diethylzinc to enones

  摘要：

  Easily available ferrocenyl substituted aziridinylmethanol FAM-4a complexes with nickel and catalyzes the enantioselective diethylzinc addition to various enones with enantiomeric excesses reaching 80%. The ligand can be recovered and used without losing its activity. The sense of induction was found to be dependent on the configuration of the aziridine ring. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.015

文献信息

• Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Mika Ogawa、Takanori Shibata

  DOI：10.1002/anie.200906839

  日期：2010.3.22

  A whole lot o' metal: An efficient copper‐catalyzed asymmetric conjugate addition was achieved using a binol‐derived ligand. The catalytic system has a turnover number of 2000, and the excellent catalytic performance could be attributed to the generation of a multinuclear complex such as 1. binol=2,2′‐dihydroxy‐1,1′‐binaphthyl.

  大量金属：使用由多元醇衍生的配体实现了铜的高效催化不对称共轭物的添加。该催化系统的周转数为2000，出色的催化性能可归因于多核络合物（如1）的生成。binol = 2,2'-二羟基-1,1'-联萘基。
• Copper-Catalyzed Enantioselective Conjugate Addition of Diethylzinc to Acyclic Enones in the Presence of Planar-Chiral Phosphaferrocene-Oxazoline Ligands
  作者：Ryo Shintani、Gregory C. Fu

  DOI：10.1021/ol026651c

  日期：2002.10.1

  [reaction: see text] A new subclass of chiral phosphaferrocene-oxazoline ligands has been applied to the copper-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones, furnishing good enantioselectivity. The ligand design readily lends itself to modification, thereby facilitating optimization of ee. Although the dominant stereocontrol element in these 1,4-addition processes is the

  [反应：见正文]手性磷二茂铁-恶唑啉配体的新亚类已被用于铜催化的二乙基锌向无环烯酮的不对称共轭加成反应，从而提供了良好的对映选择性。配体设计易于进行修饰，从而促进ee的优化。尽管在这些1，4-加成过程中主要的立体控制元素是配体的恶唑啉亚基的中心手性，而不是磷二茂铁的平面手性，改变磷二茂铁亚基可以提供对映选择性的有用增强。
• BINAM-mono-PHOS as New Entry for Multinuclear Copper Catalysts in Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Takanori Shibata、Ryotaro Takayama

  DOI：10.1055/s-0033-1338439

  日期：——

  BINAM-PHOS, participate in the copper-catalyzed asymmetric conjugate addition of organozinc reagents to enones. The incorporation of benzoyl derivatives on nitrogen atoms was crucial to promote the reaction. ­Notably, BINAM-PHOS derivatives gave the opposite major enantiomers to that obtained using BINOL-PHOS derivatives, which we have developed for the construction of multinuclear catalysts.

  易于官能化的配体 BINAM-PHOS 参与铜催化的有机锌试剂与烯酮的不对称共轭加成。在氮原子上引入苯甲酰基衍生物对于促进反应至关重要。值得注意的是，BINAM-PHOS 衍生物提供了与使用 BINOL-PHOS 衍生物获得的主要对映体相反的主要对映体，我们为构建多核催化剂而开发了 BINOL-PHOS 衍生物。
• Efficiency of Industrially Relevant Atropisomeric Diphosphines in Copper-Catalyzed 1,4-Asymmetric Conjugate Addition of Dialkylzincs to Cyclic or Acyclic Enones or Dienones
  作者：Christophe Crévisy、Virginie Ratovelomanana-Vidal、Marc Mauduit、Marie Morin、Thomas Vives、Olivier Baslé

  DOI：10.1055/s-0034-1378813

  日期：——

  Industrially relevant atropisomeric diphosphines such as 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP), 6,6-bis(diphenylphosphino)-2,2,3,3-tetrahydro-5,5-bi-1,4-benzodioxin (SYNPHOS), and 5,5-bis(diphenylphosphino)-2,2,2,2-tetrafluoro-4,4-bi-1,3-benzodioxole (DIFLUORPHOS) have demonstrated their efficiency in the copper-catalyzed asymmetric conjugate addition of various dialkylzincs to -aryl enones, -aryl dienones, and cyclic dienones. Excellent 1,4- or 1,6-regioselectivities and enantioselectivities (up to 97% ee) were attained, even with challenging sterically hindered Michael acceptors.
• Enantioselective conjugate addition of dialkylzincs to α,β-unsaturated enones catalyzed by Ni(acac)2 and (+)-(1S,2R)-7,7-dimethyl-1-morpholinoisonorborneol
  作者：Chih-Hao Tseng、Yu-Ming Hung、Biing-Jiun Uang

  DOI：10.1016/j.tetasy.2012.01.010

  日期：2012.1

  A mixture of chiral ligand 4 [(+)-MINBOL] and Ni(acac)(2) (12.5 and 0.5 mol % respectively) is able to successfully catalyze the enantioselective conjugate 1,4-addition of dialkylzinc to alpha,beta-unsaturated enones in propionitrile to give the corresponding chiral Michael adducts in good yields and with high enantioselectivities (up to 93% ee). (C) 2012 Elsevier Ltd. All rights reserved.