(3S)-1-phenyl-3-(4-cyanophenyl)-pentanone | 1350308-18-7

• 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: (3S)-1-phenyl-3-(4-cyanophenyl)-pentanone
• 英文别名: 1-phenyl-3-(4-cyanophenyl)-pentanone；4-[(3S)-1-oxo-1-phenylpentan-3-yl]benzonitrile
• CAS: 1350308-18-7
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: UAZIULMIXGXBQN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-cyanochalcone 、 diethylzinc 在 bis(acetylacetonate)nickel(II) 、 (1S,2R,4R)-7,7-dimethyl-1-morpholin-4-yl-bicyclo[2.2.1]heptan-2-ol 、 盐酸 作用下， 以 丙腈 、 水 为溶剂， 反应 48.25h， 生成 (3S)-1-phenyl-3-(4-cyanophenyl)-pentanone 、 (3R)-1-phenyl-3-(4-cyanophenyl)-pentanone
  参考文献：
  名称：

  Enantioselective conjugate addition of dialkylzincs to α,β-unsaturated enones catalyzed by Ni(acac)2 and (+)-(1S,2R)-7,7-dimethyl-1-morpholinoisonorborneol

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.01.010

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。
• US8304581B2
  申请人：——

  公开号：US8304581B2

  公开（公告）日：2012-11-06
• 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.