(2E)-3-(4-tert-butylphenyl)-1-pyrrol-1-yl-2-propen-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-(4-tert-butylphenyl)-1-pyrrol-1-yl-2-propen-1-one
• 英文别名: (E)-3-(4-tert-butylphenyl)-1-pyrrol-1-ylprop-2-en-1-one
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: GEFAXCWDNAIOOJ-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 (2E)-3-(4-tert-butylphenyl)-1-pyrrol-1-yl-2-propen-1-one 在 (1S,2S,6R)-2-diphenylphosphinyl-6-(4,5-difluoro-2-phenoxy)cyclohexanol 、 gadolinium(III) isopropoxide 2,6-二甲基苯酚 作用下， 以 丙腈 为溶剂， 反应 2.0h， 以89%的产率得到(2R)-2-(4-tert-butylphenyl)-4-oxo-4-pyrrol-1-ylbutanenitrile
  参考文献：
  名称：

  EP1995250

  摘要：

  公开号：

文献信息

• Catalytic Enantioselective Conjugate Addition of Cyanide to α,β-Unsaturated <i>N</i>-Acylpyrroles
  作者：Tsuyoshi Mita、Kazuki Sasaki、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja043424s

  日期：2005.1.1

  enantioselective conjugate addition of cyanide to α,β-unsaturated N-acylpyrroles was developed using the chiral gadolinium catalyst generated from Gd(OiPr)3 and d-glucose-derived ligand 2. Generally high enantioselectivity was obtained from a wide range of substrates; substrates with β-aryl and β-vinyl substituents and α,β-disubstituted substrates can now be used. Using this reaction as a key step, short-step

  使用由 Gd(OiPr)3 和 d-葡萄糖衍生的配体 2 生成的手性钆催化剂开发了氰化物与 α,β-不饱和 N-酰基吡咯的催化对映选择性共轭加成。 通常从广泛的底物获得高对映选择性; 现在可以使用带有 β-芳基和 β-乙烯基取代基的底物以及 α,β-二取代的底物。使用该反应作为关键步骤，实现了几种药物及其先导化合物的短步合成，包括 β-苯基取代的 GABA 类似物和普瑞巴林。
• Toward a rational design of the assembly structure of polymetallic asymmetric catalysts: design, synthesis, and evaluation of new chiral ligands for catalytic asymmetric cyanation reactions
  作者：Ikuo Fujimori、Tsuyoshi Mita、Keisuke Maki、Motoo Shiro、Akihiro Sato、Sanae Furusho、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2007.02.081

  日期：2007.6

  New chiral ligands (4 and 5) for polymetallic asymmetric catalysts were designed based on the hypothesis that the assembled structure should be stable when made from a stable module 8. A metal-ligand 5:6+mu-oxo+OH complex was generated from Gd((OPr)-Pr-i)(3) and 4 or 5, and this complex was an improved asymmetric catalyst for the desymmetrization of meso-aziridines with TMSCN and conjugate addition of TMSCN to alpha,beta-unsaturated N-acylpyrroles, compared to the previously reported catalysts derived from 1-3. These two groups of catalysts produced opposing enantioselectivity even though the ligands had the same chirality. The functional difference in the asymmetric catalysts is derived from differences in the higher-order structure of the polymetallic catalysts. (C) 2007 Elsevier Ltd. All rights reserved.
• Ligand, Method for Producing the Same, and Catalyst Using the Ligand
  申请人：Shibasaki Masakatsu

  公开号：US20090023579A1

  公开（公告）日：2009-01-22

  Disclosed is a novel asymmetric ligand which can be synthesized by a short process at low cost and is capable of exhibiting higher catalytic activity and enantioselectivity than the conventional ligands derived from sugars. Also disclosed are a method for producing such an asymmetric ligand, and a catalyst using such an asymmetric ligand. Specifically disclosed is a ligand represented by the general formula I below or the like. (In the formula, R 1 and R 2 independently represent 0-5 substituents; X represents P, As or N; m represents an integer of 0-7; n represents an integer of 0-3; A 1 -A 4 independently represent hydrogen, fluorine, chlorine, bromine, benzoyl or acetyl, or alternatively A 2 and A 3 combine together to form a ring.)
• US7820862B2
  申请人：——

  公开号：US7820862B2

  公开（公告）日：2010-10-26
• EP1995250
  申请人：——

  公开号：——

  公开（公告）日：——