(S)-3-(4-chlorophenyl)-1-phenylpentan-1-one

• 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: (S)-3-(4-chlorophenyl)-1-phenylpentan-1-one
• 英文别名: (+)-(3S)-3-(4-chlorophenyl)-1-phenylpentan-1-one；(S)-(+)-3-(4-chlorophenyl)-1-phenyl-1-pentanone；(S)-(-)-3-(4-chlorophenyl)-1-phenylpentan-1-one；(S)-1-phenyl-3-(4-chlorophenyl)-1-pentanone；(S)-1-phenyl-3-(4-chlorophenyl)pentan-1-one；(S)-3-(4-chlorophenyl)-1-phenyl-1-pentanone；(3S)-3-(4-chlorophenyl)-1-phenylpentan-1-one
• 化学式: C₁₇H₁₇ClO
• 分子量: 272.774
• InChiKey: PIGYMBPWPJCUAG-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  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-(4-chlorophenyl)-1-phenylpentan-1-one
  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

• Enantioselective Catalytic Conjugate Addition of Dialkylzinc Reagents using Copper–Phosphoramidite Complexes; Ligand Variation and Non-linear Effects
  作者：Leggy A Arnold、Rosalinde Imbos、Alessandro Mandoli、André H.M de Vries、Robert Naasz、Ben L Feringa

  DOI：10.1016/s0040-4020(00)00142-3

  日期：2000.4

  cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.’s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic

  合成了多种新的手性亚磷酰胺，并在铜催化的对乙基己烯酮和查耳酮的铜催化对映选择性共轭加成中进行了测试，以评估对立体控制至关重要的结构特征。空间要求高的胺部分对于达到高ee是必不可少的。发现查尔酮的对映选择性高达89％，环烯酮的对映选择性高达98％。对具有最佳配体的环己烯酮和查尔酮的非线性效应的研究表明，环状和非环状烯酮均具有明显的非线性效应。
• Multinuclear Cu-Catalysts Based on SPINOL-PHOS in Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Daisuke Hamada、Sayuri Yakeishi、Mika Ogawa、Takanori Shibata

  DOI：10.1021/ol300748d

  日期：2012.5.4

  Multinuclear Cu/Zn complex-catalyzed efficient asymmetric conjugate addition of organozinc reagents to acyclic and cyclic enones has been developed in the presence of a wide variety of regioisomeric chiral diols bearing phosphorus moieties as ligands. The regioisomeric SPINOL-PHOS ligands based on a SPINOL architecture showed an unexpected inversion of stereoselectivity.

  在存在多种带有磷部分作为配体的区域异构手性二醇的情况下，已经开发出有机锌试剂向无环和环状烯酮的多核Cu / Zn络合物催化的有机锌试剂的有效不对称共轭加成。基于SPINOL体系结构的区域异构SPINOL-PHOS配体表现出意想不到的立体选择性反转。
• 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。
• Enantioselective conjugate addition of diethylzinc to acyclic enones using a copper phosphino-phenol complex as catalyst
  作者：Katsuji Ito、Shuuichiro Eno、Bunnai Saito、Tsutomu Katsuki

  DOI：10.1016/j.tetlet.2005.04.036

  日期：2005.6

  Newly designed phosphino-phenol 1c was found to be an efficient chiral auxiliary for copper-mediated asymmetric conjugate addition of diethylzinc to acyclic enones. High enantioselectivity up to >99% ee was achieved in the reaction of acyclic α,β-enones.

  发现新设计的膦酚1c是铜介导的非乙基烯酮的二乙基锌的铜介导的不对称共轭加成的有效手性助剂。在无环α，β-烯酮的反应中实现了高达> 99％ee的高对映选择性。
• The Cu-catalyzed asymmetric conjugate addition with chiral diphosphite ligands derived from <scp>D</scp>-(-)-tartaric acid
  作者：Zeng-Bo Pang、Mi Tian、Hai-Feng Li、Lai-Lai Wang

  DOI：10.1080/00397911.2016.1278231

  日期：2017.3.19

  diphosphite ligands, which were derived from D-(-)-tartaric acid, have been synthesized and successfully applied in the Cu-catalyzed asymmetric conjugate addition of organozincs to enones. There was a synergic effect between the stereogenic centers of the D-(-)-tartaric acid skeleton and the axially H8-binaphthyl moieties of ligand 2c. And ligand 2c shows a comparative catalytic performance to ligand 1-N-benzylpyrrolidine-3

  摘要 合成了一系列衍生自 D-(-)-酒石酸的二亚磷酸酯配体，并成功应用于 Cu 催化的有机锌与烯酮的不对称共轭加成。D-(-)-酒石酸骨架的立体中心与配体2c的轴向H8-联萘部分之间存在协同效应。配体 2c 显示了与配体 1-N-benzylpyrrolidine-3,4-bis[(S)-1,1'-H8-binaphthyl-2,2'-diyl]亚磷酸酯-L-酒石酸 1d 的比较催化性能L-(+)-酒石酸。因此，对于环状烯酮，通过简单地选择衍生自 D-(-)-酒石酸或 L-(+)-酒石酸的配体 1d 或 2c，可以以高对映选择性（ee 高达 96%）获得加成产物的两种对映异构体酸。而且，产物的对映体区分意义主要由亚磷酸联萘基团的构型决定。图形概要