1,3,5-三苯基-2-(1-苯基丙基)戊烷-1,5-二酮 | 58556-79-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 1,3,5-三苯基-2-(1-苯基丙基)戊烷-1,5-二酮
• 英文名称: 1,3,5-triphenyl-2-(1-phenylpropyl)pentane-1,5-dione
• 英文别名: 1,3,5-Triphenyl-4-(1-phenylpropyl)-1,5-pentandion
• CAS: 58556-79-9
• 化学式: C₃₂H₃₀O₂
• 分子量: 446.589
• InChiKey: POHKEBXJKVAEGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  diethylzinc 、 苯亚甲基苯乙酮 在 (R)-(2-(tert-butylsulfinyl)-6-methoxyphenyl)diphenylphosphine 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以41%的产率得到1-戊酮,1,3-二苯基-,(3R)-
  参考文献：
  名称：

  具有手性亚砜-膦配体的铜催化二乙基锌与无环烯酮的对映选择性共轭加成

  摘要：

  通过手性亚砜-膦（SOP）配体可实现铜催化的二乙基锌向无环烯酮的对映选择性共轭加成反应。此过程显示出良好的官能团耐受性，并得到具有优异对映选择性（最高96％ee）的1，4-加合物。

  DOI：

  10.1016/j.tet.2015.12.062

文献信息

• Enantioselective Conjugate Addition of Diethylzinc to Enones with Chiral Copper-QUIPHOS Catalyst Influence of the Addition of Water on the Enantioselectivity
  作者：Guillaume Delapierre、Thierry Constantieux、Jean Michel Brunel、Gérard Buono

  DOI：10.1002/1099-0690(200007)2000:13<2507::aid-ejoc2507>3.0.co;2-t

  日期：2000.7

  The use of a new chiral copper catalyst involving QUIPHOS as ligand in the 1,4-addition of Et2Zn to enones is reported. The dramatic beneficial effect of addition of water or Zn(OH)(2) to this system has been investigated, and led to an improvement of the enantiomeric excess from 7 to 61% ee.
• Application of deoxycholic acid-based copper–phosphite complexes as ligands in the enantioselective conjugate addition of diethylzinc to acyclic enones
  作者：Anna Iuliano、Patrizia Scafato

  DOI：10.1016/s0957-4166(03)00044-2

  日期：2003.3

  Four phosphites obtained by linking enantiomerically pure binaphthylchlorophosphite to the two different hydroxy groups of deoxycholic acid were synthesized and used as chiral ligands in the enantioselective copper-catalyzed 1,4-addition of diethylzinc to acyclic enones. The ligands were screened for activity and enantioselectivity using chalcone as the substrate to establish the influence of the absolute configuration of the binaphthyl moiety as well as the position on the cholestanic backbone of the phosphite moiety. The ligand affording the best results was eventually used in the copper-catalyzed 1,4-addition to various acyclic enones, affording the alkylation products in good yields and e.e.s up to 78%. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones with chiral sulfoxide–phosphine ligands
  作者：Tingting Yang、Yongling Zhang、Peng Cao、Min Wang、Li Li、Dong Li、Jian Liao

  DOI：10.1016/j.tet.2015.12.062

  日期：2016.5

  The copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones was achieved with chiral sulfoxide–phosphine (SOP) ligands. This process showed good functional group tolerance and gave the 1, 4-adducts with excellent enantioselectivities (up to 96% ee).

  通过手性亚砜-膦（SOP）配体可实现铜催化的二乙基锌向无环烯酮的对映选择性共轭加成反应。此过程显示出良好的官能团耐受性，并得到具有优异对映选择性（最高96％ee）的1，4-加合物。