(S)-3-(4-fluorophenyl)-1-phenylpentan-1-one | 1226984-53-7

• 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-fluorophenyl)-1-phenylpentan-1-one
• 英文别名: (3S)-3-(4-fluorophenyl)-1-phenylpentan-1-one
• CAS: 1226984-53-7
• 化学式: C₁₇H₁₇FO
• 分子量: 256.32
• InChiKey: DBXYZSHKIFQROE-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  2

反应信息

• 作为产物：
  描述：

  diethylzinc 、 4-fluorochalcone 在 (S)-N-((1R,2R)-2-(diphenylphosphino)cyclohexyl)pyrrolidine-2-carboxamide 、 copper(II) acetate monohydrate 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以83%的产率得到
  参考文献：
  名称：

  铜催化二烷基锌试剂向α，β-和α，β，γ，δ-不饱和酮的对映选择性1,4-共轭加成

  摘要：

  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）。

  DOI：

  10.1016/j.tet.2019.05.029

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-catalyzed 1,4-addition of dialkylzincs to enones using a novel N,N,P–Cu(II) complex
  作者：Yasuhiro Ebisu、Kenjiro Kawamura、Masahiko Hayashi

  DOI：10.1016/j.tetasy.2012.06.010

  日期：2012.7

  Enantioselective copper-catalyzed 1,4-additions of dialkylzincs to enones were carried out in the presence of 1 mol % of Cu(OTf)(2) and 2.5 mol % of an N,N,P-ligand possessing a tert-butyl group at the adjacent position of the nitrogen of pyridine to afford the corresponding 1,4-adducts in up to 98% ee. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.
• US8304581B2
  申请人：——

  公开号：US8304581B2

  公开（公告）日：2012-11-06