3-(4,4,4-Trifluoro-3-oxo-1-butenyl)benzonitrile | 101048-56-0

• 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: 3-(4,4,4-Trifluoro-3-oxo-1-butenyl)benzonitrile
• 英文别名: 3-[(E)-4,4,4-trifluoro-3-oxobut-1-enyl]benzonitrile
• CAS: 101048-56-0
• 化学式: C₁₁H₆F₃NO
• 分子量: 225.17
• InChiKey: ZEZRYTQCLJZJSI-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (R)-(+)-[(1-phenylethyl)amino]-2-cyclohexen-1-one 、 3-(4,4,4-Trifluoro-3-oxo-1-butenyl)benzonitrile 生成 3-[4,4,4-Trifluoro-3-oxo-1-[2-oxo-6-(1-phenylethylimino)cyclohexyl]butyl]benzonitrile
  参考文献：
  名称：

  Process for synthesis of alpha,beta-unsaturated ketones

  摘要：

  本文描述了一种合成α,β-不饱和酮的方法，该酮可用于制备取代的1,4-二氢吡啶，方法是将醛与吡咯烷反应，然后在低温下加入酮，最后加入三氟乙酸。该合成方法用于制备取代的1,4-二氢吡啶的过程中，其中通过将1,3-环己二酮与苯乙胺反应制备出一种缩聚胺。α,β-不饱和酮可以与缩聚胺反应形成1,5-二酮，该化合物可以转化为取代的1,4-二氢吡啶。

  公开号：

  US20040039234A1
• 作为产物：
  描述：

  四氢吡咯 、 1,1,1-三氟丙酮 、 3-氰基苯甲醛 以 二氯甲烷 为溶剂， 以77%的产率得到3-(4,4,4-Trifluoro-3-oxo-1-butenyl)benzonitrile
  参考文献：
  名称：

  An asymmetric synthesis of a 4-substituted-1,4-dihydropyridine

  摘要：

  A concise, convergent asymmetric synthesis of the 4-substituted-1,4-dihydropyridine 1 [Ohntnacht, C. J.. Jr.: Trainor, D. A.: Forst, J. M.; Stein, M. M.: Harris. R. J. Patent No. 5,622, 964] has been achieved via a novel asymmetric Michael addition of an optically pure vinylogous amide to all alpha,beta-unsaturated ketone. The overall process is three steps front readily available starting materials and provides an economical manufacturing route to (lie title compound, which was required as a candidate drug for the treatment of urinary incontinence. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00975-9

文献信息

• Process for asymmetric synthesis of substituted 1,4 -dihydropyridines
  申请人：——

  公开号：US20040039207A1

  公开（公告）日：2004-02-26

  A process is described for reacting a vinylogous amide with an &agr;,&bgr;-unsaturated ketone in the presence of a silicon compound to form an 1,5-diketone which is converted to a 1,4-dihydropyridine. Asymmetric substituted 1,4-dihydropyridines are synthesized by the process by preparing an asymmetric vinylogous amide by reacting a 1,3-cyclohexanedione with a substantially homo-chiral phenylethylamine. Reaction of the asymmetric vinylogous amide with an &agr;,&bgr;-unsaturated ketone in the presence of a silicon compound forms an asymmetric 1,5-diketone. The 1,5-diketone is converted to an asymmetric substituted 1,4-dihydropyridine.

  该过程描述了在硅化合物存在下，将一种vinyl羰胺与一种α，β-不饱和酮反应生成1,5-二酮，该化合物转化为1,4-二氢吡啶。通过将1,3-环己二酮与基本上同构手性苯乙胺反应以制备不对称的vinyl羰胺，通过在硅化合物存在下将不对称的vinyl羰胺与α，β-不饱和酮反应形成不对称的1,5-二酮。该1,5-二酮转化为不对称取代的1,4-二氢吡啶，从而合成了不对称取代的1,4-二氢吡啶。
• [EN] PROCESS FOR SYNTHESIS OF alpha , beta -UNSATURATED KETONES<br/>[FR] PROCEDE DE SYNTHESE DE CETONES DOLLAR G(A), DOLLAR G(B) INSATUREES
  申请人：ASTRAZENECA AB

  公开号：WO2002010103A1

  公开（公告）日：2002-02-07

  A method for the synthesis of an α,β-unsaturated ketone useful for making substituted 1,4-dihydropyridines is described by reacting an aldehyde with pyrrolidine and then adding a ketone followed by trifluoroacetic acid at low temperature. The synthesis is used in a process for making substituted 1,4-dihydropyridines wherein a vinylogous amide is prepared by reacting a 1,3-cyclohexanedione with a phenylethylamine. The α,β-unsaturated ketone can be reacted with a vinylogous amide to form a 1,5-diketone which can be converted to a substituted 1,4-dihydropyridine.

  本发明涉及一种合成α，β-不饱和酮的方法，该酮可用于制备取代的1,4-二氢吡啶。该方法是通过将醛与吡咯烷反应，然后在低温下加入酮，随后加入三氟乙酸来完成的。该合成方法用于制备取代的1,4-二氢吡啶的过程中，其中通过将1,3-环己二酮与苯乙胺反应制备了一个共轭酰胺。α，β-不饱和酮可以与共轭酰胺反应形成1,5-二酮，该1,5-二酮可以转化为取代的1,4-二氢吡啶。
• [EN] PROCESS FOR ASYMMETRIC SYNTHESIS OF SUBSTITUTED 1,4-DIHYDROPYRIDINES<br/>[FR] PROCEDE DE SYNTHESE ASYMETRIQUE DE 1,4- DIHYDROPYRIDINES SUBSTITUEES
  申请人：ASTRAZENECA AB

  公开号：WO2002010134A1

  公开（公告）日：2002-02-07

  A process is described for reacting a vinylogous amide with an α,β-unsaturated ketone in the presence of a silicon compound to form an 1,5-diketone which is converted to an 1,4-dihydropyridine. Asymmetric substituted 1,4-dihydropyridines are synthesized by the process by preparing an asymmetric vinylogous amide by reacting a 1,3-cyclohexanedione with a substantially homo-chiral phenylethylamine. Reaction of the asymmetric vinylogous amide with an α,β-unsaturated ketone in the presence of a silicon compound forms an asymmetric 1,5-diketone. The 1,5-diketone is converted to an asymmetric substituted 1,4-dihydropyridine.

  本文描述了一种使用硅化合物催化反应含乙烯基酰胺的化合物和α，β-不饱和酮，生成1,5-二酮并转化为1,4-二氢吡啶的过程。通过使用1,3-环己二酮和手性苯乙胺反应制备手性含乙烯基酰胺，然后将手性含乙烯基酰胺与α，β-不饱和酮在硅化合物的存在下反应生成手性1,5-二酮，最终转化为手性取代的1,4-二氢吡啶。
• PROCESS FOR SYNTHESIS OF $g(a),$g(b)-UNSATURATED KETONES
  申请人：AstraZeneca AB

  公开号：EP1307420A1

  公开（公告）日：2003-05-07
• PROCESS FOR ASYMMETRIC SYNTHESIS OF SUBSTITUTED 1,4-DIHYDROPYRIDINES
  申请人：AstraZeneca AB

  公开号：EP1307429A1

  公开（公告）日：2003-05-07