(S)-3-(3-chlorophenyl)-1-phenylpentan-1-one | 408359-53-5

• 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-(3-chlorophenyl)-1-phenylpentan-1-one
• 英文别名: (3S)-1-phenyl-3-(3-chlorophenyl)-pentanone；1-phenyl-3-(3-chlorophenyl)pentanone；(3S)-3-(3-Chlorophenyl)-1-phenyl-1-pentanone；(3S)-3-(3-chlorophenyl)-1-phenylpentan-1-one
• CAS: 408359-53-5
• 化学式: C₁₇H₁₇ClO
• 分子量: 272.774
• InChiKey: CXWITJJCWOPMHA-ZDUSSCGKSA-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：

  3-(3-chlorophenyl)-1-phenylprop-2-en-1-one 、 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 24.25h， 以83%的产率得到(S)-3-(3-chlorophenyl)-1-phenylpentan-1-one
  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

• 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）。
• Synthesis of N,N-dimethyl-2-amino-1,2-dicyclohexylethanol and its application in the enantioselective conjugate addition of diethylzinc to enones: a convenient upgrade of the chiral ligand via hydrogenation
  作者：Pui-Erh Tong、Pei Li、Albert S.C. Chan

  DOI：10.1016/s0957-4166(01)00406-2

  日期：2001.9

  The effectiveness of N,N-dimethyl-2-amino-1,2-diphenylethanol as a chiral ligand was significantly improved via simple hydrogenation of the phenyl rings. Both the catalytic activity and the enantioselectivity of the resulting new ligand in the asymmetric conjugate addition of diethylzinc to enones were found to be superior to the original phenyl analog.

  N，N-二甲基-2-氨基-1,2-二苯基乙醇作为手性配体的有效性通过苯环的简单氢化而得到显着改善。发现二乙基锌与烯酮的不对称共轭加成中所得新配体的催化活性和对映选择性均优于原始苯基类似物。
• 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.