(+)-3-(4-methylphenyl)-1-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: (+)-3-(4-methylphenyl)-1-phenyl-pentan-1-one
• 英文别名: (+)-3-(4-methylphenyl)-1-phenylpentan-1-one；(+)-1-phenyl-3-(p-tolyl)pentan-1-one；1-phenyl-3-p-tolylpentan-1-one；3-(4-Methylphenyl)-1-phenylpentan-1-one
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: FJWSPPSFGALARR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (+)-3-(4-methylphenyl)-1-phenyl-pentan-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

• Directed Markovnikov hydroarylation and hydroalkenylation of alkenes under nickel catalysis
  作者：Zi-Qi Li、Omar Apolinar、Ruohan Deng、Keary M. Engle

  DOI：10.1039/d1sc03121j

  日期：——

  Native Lewis basic functional groups enable the nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of unactivated alkenes with organoboron reagents.

  Native Lewis碱性官能团使镍催化的Markovnikov选择性烯烃与有机硼试剂的氢化芳基化和烯烃化反应成为可能。
• 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。
• Chiral Phosphanylferrocenecarboxamides with Amino Acid Pendant Groups as Ligands for Cu-Mediated Asymmetric Conjugate Additions of Diethylzinc to Chalcones - Structural Characterisation of Precursors to the Cu Catalyst
  作者：Jiří Tauchman、Ivana Císařová、Petr Štěpnička

  DOI：10.1002/ejoc.201000480

  日期：2010.8

  A series of chiral phosphanylferrocenecarboxamides was prepared by treatment of either 1'-(diphenylphosphanyl)-ferrocene-1-carboxylic acid (Hdpf) or its planar-chiral 1,2-isomers with amino acid methyl esters in the presence of peptide coupling agents. The compounds were characterised by spectroscopic methods, and the crystal structure of one representative was determined by X-ray diffraction. Catalytic

  在肽偶联剂的存在下，通过用氨基酸甲酯处理 1'-(二苯基膦酰基)-二茂铁-1-羧酸 (Hdpf) 或其平面手性 1,2-异构体制备了一系列手性 phosphanylferrocenecarboxamides。通过光谱方法对化合物进行表征，并通过 X 射线衍射确定了一个代表的晶体结构。这些供体在铜催化的二乙基锌与查耳酮的不对称共轭加成反应中的催化测试表明，反应结果对配体结构和反应条件（铜源和溶剂）高度敏感，而查耳酮取代基（Me、MeO 或 Cl在位置 4 或 4') 的影响不那么明显。基于 Hdpf 的化合物被证明是比它们的平面手性类似物更好的配体。在优化条件下，与 L-缬氨酸-Hdpf 共轭物、(S)-Ph 2 PfcCONHCH(CHMe 2 )-CO 2 Me (fc = 二茂铁-1,1'-二基) 和未取代的查耳酮反应得到完全转化率 (20 °C/ 4 h) 和 87 % ee。氨基膦
• Highly Enantioselective Conjugate Addition of Diethylzinc to Acyclic Enones with Fine-Tunable Phosphite−Pyridine Ligands
  作者：Huihui Wan、Yuanchun Hu、Yuxue Liang、Shuang Gao、Junwei Wang、Zhuo Zheng、Xinquan Hu

  DOI：10.1021/jo0345897

  日期：2003.10.1

  and (S)-2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-1,1'-biphenyl was employed in Cu(I)-catalyzed conjugate addition of diethylzinc to acyclic enones. Excellent enantioselectivities (up to 98% ee) and highly catalytic activities were achieved for a variety of acyclic enones.

  由（S）-2-氨基-2'-羟基-6,6'-二甲基-1,1'-联苯和（S）-2衍生的一系列新的亚磷酸酯-吡啶微调（P，N）配体-氨基-2'-羟基-4,4'，6,6'-四甲基-1,1'-联苯用于二乙基锌与无环烯酮的Cu（I）催化共轭加成反应。各种无环烯酮均具有出色的对映选择性（高达98％ee）和高度催化活性。
• 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。