(S)-1-phenyl-3-(2-methoxyphenyl)-1-pentanone

• 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)-1-phenyl-3-(2-methoxyphenyl)-1-pentanone
• 英文别名: 3-(2-methoxyphenyl)-1-phenylpentan-1-one；(S)-3-(2-methoxyphenyl)-1-phenylpentan-1-one；(3S)-1-phenyl-3-(2-methoxyphenyl)-pentanone；1-phenyl-3-(2-methoxyphenyl)pentanone；(3S)-3-(2-methoxyphenyl)-1-phenylpentan-1-one
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: HDBGLKAJXBPMPR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

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)-1-phenyl-3-(2-methoxyphenyl)-1-pentanone
  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

• METHOD OF ENANTIOSELECTIVE ADDITION TO ENONES
  申请人：UANG Biing-Jiun

  公开号：US20110282101A1

  公开（公告）日：2011-11-17

  The present invention relates to a method of enantioselective addition to enones, including: reacting R 3 (CH 2 ) p CH═CR 5 C(═O)Y(CH 2 ) q R 4 with R 6 ZnR 7 in the presence of a compound represented by the following formula (I) and a transition metal catalyst, in which Y, p, q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined the same as the specification. Accordingly, the present invention can perform asymmetric conjugate addition in high yields and enantioselectivity.

  本发明涉及一种对烯酮进行对映选择性加成的方法，包括：在存在以下式（I）所代表的化合物和过渡金属催化剂的情况下，将R3(CH2)pCH═CR5C(═O)Y(CH2)qR4与R6ZnR7反应，其中Y、p、q、R1、R2、R3、R4、R5、R6和R7的定义与规范相同。因此，本发明可以在高产率和对映选择性下进行不对称共轭加成。
• 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.
• Enantioselective conjugate addition of dialkylzincs to α,β-unsaturated enones catalyzed by Ni(acac)2 and (+)-(1S,2R)-7,7-dimethyl-1-morpholinoisonorborneol
  作者：Chih-Hao Tseng、Yu-Ming Hung、Biing-Jiun Uang

  DOI：10.1016/j.tetasy.2012.01.010

  日期：2012.1

  A mixture of chiral ligand 4 [(+)-MINBOL] and Ni(acac)(2) (12.5 and 0.5 mol % respectively) is able to successfully catalyze the enantioselective conjugate 1,4-addition of dialkylzinc to alpha,beta-unsaturated enones in propionitrile to give the corresponding chiral Michael adducts in good yields and with high enantioselectivities (up to 93% ee). (C) 2012 Elsevier Ltd. All rights reserved.
• Enantioselective conjugate addition of diethylzinc to chalcones catalysed by N-trityl aziridine-2-(S)-(diphenyl)methanol and Ni(acac)2
  作者：Uma Shadakshari、Sandip K Nayak

  DOI：10.1016/s0040-4020(01)00793-1

  日期：2001.9

  The chiral Ni(II) complex prepared from Ni(acac)(2) and N-trityl aziridine-2-(S)-(diphenyl)methanol catalyses the enantioselective conjugate addition of diethylzinc to chalcones in good yield with ces of upto 93%. (C) 2001 Elsevier Science Ltd. All rights reserved.
• US8304581B2
  申请人：——

  公开号：US8304581B2

  公开（公告）日：2012-11-06