(+)-3-(naphthalen-2-yl)-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: (+)-3-(naphthalen-2-yl)-1-phenylpentan-1-one
• 英文别名: 3-(naphthalen-2-yl)-1-phenylpentan-1-one；3-Naphthalen-2-yl-1-phenylpentan-1-one；3-naphthalen-2-yl-1-phenylpentan-1-one
• 化学式: C₂₁H₂₀O
• 分子量: 288.389
• InChiKey: OPAUWGAMCYLVIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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-(naphthalen-2-yl)-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

• 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。
• 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。