(R)-3-(4-fluorophenyl)-1-phenylpentan-1-one | 1373558-42-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (R)-3-(4-fluorophenyl)-1-phenylpentan-1-one
• 英文别名: (3R)-3-(4-fluorophenyl)-1-phenylpentan-1-one
• CAS: 1373558-42-9
• 化学式: C₁₇H₁₇FO
• 分子量: 256.32
• InChiKey: DBXYZSHKIFQROE-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  diethylzinc 、 4-fluorochalcone 在 copper(II) choride dihydrate 、 (R)-BINOL-XPHOS 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到(R)-3-(4-fluorophenyl)-1-phenylpentan-1-one
  参考文献：
  名称：

  用于铜催化不对称共轭添加有机锌试剂的多核催化剂

  摘要：

  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。

  DOI：

  10.1002/anie.200906839

文献信息

• Functionalized BINOL-<i>mono</i>-PHOS for Multinuclear Cu-Catalysts in Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Sayuri Yakeishi、Daisuke Hamada、Takanori Shibata

  DOI：10.1246/cl.130080

  日期：2013.5.5

  Functionalization of BINOL-mono-PHOS achieved the Cu-catalyzed highly asymmetric conjugate addition of organozinc reagents to enones. The incorporation of a bulky hydroxy group at the 3′-position o...

  BINOL-mono-PHOS 的功能化实现了铜催化的有机锌试剂与烯酮的高度不对称共轭加成。在 3'-位 o...
• Copper-catalyzed enantioselective 1,4-conjugate addition of dialkylzinc reagents to α,β- and α,β,γ,δ-unsaturated ketones
  作者：Rukeya Rexiti、Jian Lu、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tet.2019.05.029

  日期：2019.6

  An enantioselective Cu(II)-catalyzed conjugate addition of dialkylzinc reagents to α,β- or α,β,γ,δ-unsaturated ketones with chiral cyclohexane-based amidophosphine ligands was developed. With 2 mol% of Cu(OAc)2·H2O/L5, the conjugate addition of diethylzinc to α,β-unsaturated ketones was achieved in good-to-excellent yields (up to 98%) and high enantioselectivities (up to 92% ee). This catalytic system

  开发了一种手性环己烷基酰胺基膦配体的对映选择性Cu（II）催化二烷基锌试剂共轭加成到α，β-或α，β，γ，δ-不饱和酮上的方法。使用2 mol％的Cu（OAc）2 ·H 2 O / L5，可以将二乙基锌共轭添加到α，β-不饱和酮中，收率良好至优异（最高98％），对映选择性高（最高90％）。 92％ee）。该催化体系显示对于将Et 2 Zn 1，（4 - E）加成到（2 E，4 E）-1,5-二苯基戊-2,4-dien-1-one上是有效的，产率为85％，90 ％ee。另外，Cu（OTf）2 / L11为1摩尔％，α，β，γ，δ-不饱和酮的共轭加成反应具有1,4-区域选择性，良好的收率（79-86％）和出色的对映选择性（高达97％ee）。
• Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones with chiral sulfoxide–phosphine ligands
  作者：Tingting Yang、Yongling Zhang、Peng Cao、Min Wang、Li Li、Dong Li、Jian Liao

  DOI：10.1016/j.tet.2015.12.062

  日期：2016.5

  The copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones was achieved with chiral sulfoxide–phosphine (SOP) ligands. This process showed good functional group tolerance and gave the 1, 4-adducts with excellent enantioselectivities (up to 96% ee).

  通过手性亚砜-膦（SOP）配体可实现铜催化的二乙基锌向无环烯酮的对映选择性共轭加成反应。此过程显示出良好的官能团耐受性，并得到具有优异对映选择性（最高96％ee）的1，4-加合物。
• Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones using a novel N,N,P–Cu(II) complex
  作者：Yasuhiro Ebisu、Kenjiro Kawamura、Masahiko Hayashi

  DOI：10.1016/j.tetasy.2012.06.010

  日期：2012.7

  Enantioselective copper-catalyzed 1,4-additions of dialkylzincs to enones were carried out in the presence of 1 mol % of Cu(OTf)(2) and 2.5 mol % of an N,N,P-ligand possessing a tert-butyl group at the adjacent position of the nitrogen of pyridine to afford the corresponding 1,4-adducts in up to 98% ee. (C) 2012 Elsevier Ltd. All rights reserved.
• Enantioselective copper(II)-catalyzed conjugate addition of diethylzinc to β-substituted enones utilizing BINOL-based phosphoramidite ligands
  作者：Wenxian Zhao、Tao Wang、Ruijuan Zhao、Huanping Xie、Lantao Liu

  DOI：10.1016/j.tetasy.2016.01.016

  日期：2016.3

  A family of new chiral phosphoramidite ligands based on 3,3'-disubstituted (S)-BINOL have been successfully synthesized. The chiral phosphoramidite ligands were subsequently applied to the copper(II)-catalyzed enantioselective addition of diethylzinc to beta-substituted enones, giving the desired chiral adducts with enantioselectivities of up to 93% ee and high yields (up to 88%). (C) 2016 Elsevier Ltd. All rights reserved.