(R)-3-(2-chlorophenyl)-1-phenylpentan-1-one | 879507-11-6

• 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: (R)-3-(2-chlorophenyl)-1-phenylpentan-1-one
• 英文别名: (3R)-3-(2-chlorophenyl)-1-phenylpentan-1-one
• CAS: 879507-11-6
• 化学式: C₁₇H₁₇ClO
• 分子量: 272.774
• InChiKey: PQUDZXHLXARZFF-CYBMUJFWSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  393.6±25.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：

  2-氯查耳酮 、 diethylzinc 在 copper acetylacetonate chiral amino alcohol-based tridentate ligand 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 16.0h， 以98%的产率得到(R)-3-(2-chlorophenyl)-1-phenylpentan-1-one
  参考文献：
  名称：

  Highly enantioselective conjugate addition of diethylzinc to substituted chalcones catalyzed by Cu(II) complexes of a tridentate P,N,O ligand

  摘要：

  A new series of tridentate P,N,O ligands having hard and soft donor atoms derived from chiral amino alcohols were developed and employed in the Cu(II)-catalyzed conjugate addition of diethylzinc to substituted chalcones. The asymmetric additions to a variety of substituted chalcones afforded products in excellent yields and good to excellent enantioselectivities up to 97% ee. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.027

文献信息

• Copper-catalyzed enantioselective 1,4-conjugate addition of dialkylzinc reagents to α,β- and α,β,γ,δ-unsaturated ketones
  作者：Rukeya Rexiti、Jian Lu、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tet.2019.05.029

  日期：2019.6

  An enantioselective Cu(II)-catalyzed conjugate addition of dialkylzinc reagents to α,β- or α,β,γ,δ-unsaturated ketones with chiral cyclohexane-based amidophosphine ligands was developed. With 2 mol% of Cu(OAc)2·H2O/L5, the conjugate addition of diethylzinc to α,β-unsaturated ketones was achieved in good-to-excellent yields (up to 98%) and high enantioselectivities (up to 92% ee). This catalytic system

  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）。
• 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.