(-)-1-(4-chlorophenyl)-3-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: (-)-1-(4-chlorophenyl)-3-phenyl-pentan-1-one
• 英文别名: (-)-1-(4-Chlorophenyl)-3-phenylpentan-1-one；1-(4-chlorophenyl)-3-phenylpentan-1-one
• 化学式: C₁₇H₁₇ClO
• 分子量: 272.774
• InChiKey: NXVQGDRMXQLONF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  1

反应信息

• 作为产物：
  描述：

  diethylzinc 、 (2E)-1-(4-氯苯基)-3-苯基-2-丙烯-1-酮 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 (S_a,S_a)-C₄₂H₃₃N₂O₄P (NOBIN-phosphite-pyridine) 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以85%的产率得到(-)-1-(4-chlorophenyl)-3-phenyl-pentan-1-one
  参考文献：
  名称：

  二乙基锌与具有可微调的亚磷酸酯-吡啶配体的无环烯酮的高度对映选择性共轭加成。

  摘要：

  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。

  DOI：

  10.1021/jo0345897

文献信息

• Highly enantioselective 1,4-conjugate addition of diethylzinc to acyclic enones with chiral phosphite–pyridine ligands derived from H8-NOBIN
  作者：Yuanchun Hu、Xinmiao Liang、Junwei Wang、Zhuo Zheng、Xinquan Hu

  DOI：10.1016/j.tetasy.2003.09.020

  日期：2003.12

  A series of new phosphite-pyridine ligands, based on the H-8-binaphthyl backbone, were synthesized and employed in the copper-catalyzed enantioselective 1,4-conjugate addition of diethylzinc to acyclic enones. Ligands derived from (S)-H-8-NOBIN provided better results than their parent ligands in the reaction. Ligand L1 provided excellent ees for trans -4-aryl-3-buten-2-ones (up to 97.8% ee) as substrates. Ligand L2 was very efficient for various para-chalcones, and up to 97.2% ee was achieved. (C) 2003 Elsevier Ltd. All rights reserved.
• Development of New Chiral P,N Ligands and Their Application in the Cu-Catalyzed Enantioselective Conjugate Addition of Diethylzinc to Enones
  作者：Xinquan Hu、Huilin Chen、Xumu Zhang

  DOI：10.1002/(sici)1521-3773(19991203)38:23<3518::aid-anie3518>3.0.co;2-p

  日期：——

  High enantioselectivity (up to 98 % ee) has been achieved for the conjugate addition of diethylzinc to acyclic enones utilizing Cu(I) complexes of the novel chiral P,N ligands 1. The high enantioselectivities are best achieved using [Cu(OTf)](2) small middle dotC(6)H(6) as the copper catalyst precursor in nonpolar solvents such as toluene or Cl(CH(2))(2)Cl. R=H, CH(3); Tf=F(3)CSO(2).
• Readily Prepared Chiral P,N Ligands and Their Applications in Cu-Catalyzed Enantioselective Conjugate Additions
  作者：Yuanchun Hu、Xinmiao Liang、Junwei Wang、Zhuo Zheng、Xinquan Hu

  DOI：10.1021/jo0340758

  日期：2003.5.1

  A new type of phosphite-pyridine (P,N) ligand derived from (S)-NOBIN and (S)-BINOL was employed in Cu(I)-catalyzed conjugate addition of diethylzinc to chalcones. The new P,N ligands were highly efficient in the copper-catalyzed enantioselective 1,4-conjugate additions of diethylzinc to acyclic enones, and up to 97% ee was achieved.
• Development of new chiral P,N ligands and their applications in enantioselective 1,4-conjugate additions of diethylzinc to chalcones
  作者：Yuxue Liang、Shuang Gao、Huihui Wan、Yuanchun Hu、Huilin Chen、Zhuo Zheng、Xinquan Hu

  DOI：10.1016/j.tetasy.2003.09.001

  日期：2003.10

  Examples of a new type of chiral phosphine-pyridine ligand have been synthesized from (R)-2-amino-2'-hydroxy-6,6'-dimethyl-1.1'-biphenyl and (R)-2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-l,l'-biphenyl in six steps and successfully employed in Cu(I)-catalysed conjugate additions of diethylzine to chalcones. Up to 96.1% ee and high activities were achieved. (C) 2003 Elsevier Ltd. All rights reserved.
• Diastereomeric phosphite–pyridine ligands for enantioselective 1,4-conjugate additions
  作者：Xiancai Luo、Yuanchun Hu、Xinquan Hu

  DOI：10.1016/j.tetasy.2005.02.002

  日期：2005.3

  Diastercomeric phosphite-pyridine ligands derived from racemic biphenyl units and homochiral BINOL, achieved high enantioselectivities (up to 96.1%, ee) in the Cu(l)-catalysed conjugate additions Of Et2Zn to a variety of acyclic enones. (C) 2005 Elsevier Ltd. All rights reserved.