(R)-1-phenyl-3-(4-(trifluoromethyl)phenyl)pentan-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: (R)-1-phenyl-3-(4-(trifluoromethyl)phenyl)pentan-1-one
• 英文别名: (R)-1-Phenyl-3-[4-(trifluoromethyl)phenyl]-1-pentanone；(3R)-1-phenyl-3-[4-(trifluoromethyl)phenyl]pentan-1-one
• 化学式: C₁₈H₁₇F₃O
• 分子量: 306.328
• InChiKey: MJZTWECMWWRCKV-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-(trifluoromethyl)phenyl)-1-phenylprop-2-en-1-one 、 diethylzinc 在 copper(II) choride dihydrate 、 (S)-4,4'-SPINOL-PHOS 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以95%的产率得到(R)-1-phenyl-3-(4-(trifluoromethyl)phenyl)pentan-1-one
  参考文献：
  名称：

  基于SPINOL-PHOS的多核铜催化剂在有机锌试剂不对称共轭添加中的应用

  摘要：

  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。

  DOI：

  10.1021/ol300748d

文献信息

• 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 asymmetric conjugate addition of diethylzinc to substituted chalcones using a chiral phosphine ligand
  作者：Özdemir Dogan、Adnan Bulut、Savaş Polat、M. Ali Tecimer

  DOI：10.1016/j.tetasy.2011.09.003

  日期：2011.9

  A series of chiral phosphine PFAM and phosphine oxide POFAM ligands were studied for the copper-catalyzed asymmetric diethylzinc addition to enones. One of these ligands, PFAM2, was an efficient catalyst with a variety of enones to give conjugate addition products in up to 96% yield and 92% ee.

  研究了一系列手性膦PFAM和氧化膦POFAM配体，用于铜催化烯酮中不对称二乙基锌的加成。这些配体之一PFAM2是一种有效的催化剂，具有多种烯酮，可提供高达96％的收率和92％ee的共轭加成产物。
• 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。
• 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.
• 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。