(S)-4-oxo-2-phenethyl-4-(1H-pyrrol-1-yl)butanenitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (S)-4-oxo-2-phenethyl-4-(1H-pyrrol-1-yl)butanenitrile
• 英文别名: (2S)-4-oxo-2-(2-phenylethyl)-4-pyrrol-1-ylbutanenitrile
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: IPDVLUZIBABSEA-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 (2E)-5-phenyl-1-pyrrol-1-yl-2-penten-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 24.0h， 以96%的产率得到(S)-4-oxo-2-phenethyl-4-(1H-pyrrol-1-yl)butanenitrile
  参考文献：
  名称：

  EP1995250

  摘要：

  公开号：

文献信息

• Asymmetric Conjugate Hydrocyanation of α,β-Unsaturated <i>N</i>-Acylpyrroles with the Ru(phgly)₂(binap)–CH₃OLi Catalyst System
  作者：Yusuke Sakaguchi、Nobuhito Kurono、Kohei Yamauchi、Takeshi Ohkuma

  DOI：10.1021/ol403545b

  日期：2014.2.7

  Asymmetric conjugate hydrocyanation of α,β-unsaturated carboxylic acid derivatives catalyzed by a Ru[(S)-phgly]2[(S)-binap]–CH3OLi system was examined. The N-acylpyrrole gave the best result in terms of reactivity and enantioselectivity. A series of substrates with alkyl or heterosubstituted alkyl groups at the β-position reacted with a substrate-to-catalyst molar ratio of 200–2000 to afford the β-cyano

  研究了Ru [（S）-phgly] 2 [（S）-binap] -CH 3 OLi体系催化的α，β-不饱和羧酸衍生物的不对称共轭氢氰化。该ñ -acylpyrrole了反应性和对映选择性方面最好的结果。一系列在β位置具有烷基或杂取代烷基的底物与底物与催化剂的摩尔比为200–2000进行反应，得到的β-氰基产物的ee范围为88％-> 99％ee。提出了氢氰化中对映体的选择方式。
• Structural Study-Guided Development of Versatile Phase-Transfer Catalysts for Asymmetric Conjugate Additions of Cyanide
  作者：Brian A. Provencher、Keith J. Bartelson、Yan Liu、Bruce M. Foxman、Li Deng

  DOI：10.1002/anie.201105536

  日期：2011.11.4

  Unprecedented phase‐transfer catalysts for the first example of an organocatalytic asymmetric conjugate addition of cyanide with acetone cyanohydrin are reported (see scheme). Utilizing an accessible cupreidinium salt and a cyanation reagent suitable for industrial scale, this reaction holds significant promise for practical asymmetric synthesis. The catalysts were developed as a result of key structural

  报道了用于氰化物与丙酮氰醇的有机催化不对称共轭加成的第一个例子的前所未有的相转移催化剂（参见方案）。利用易于获得的铜盐和适用于工业规模的氰化试剂，该反应对实际不对称合成具有重要意义。这些催化剂是根据 X 射线分析获得的关键结构见解而开发的。
• 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.