2-cyanoethyl 2-oxobutanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-cyanoethyl 2-oxobutanoate
• 英文别名: 2-Cyanoethyl 2-oxobutanoate
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: PEEHBCXIZUCHTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙二酸环(亚)异丙酯 、 2-cyanoethyl 2-oxobutanoate 、 2-氯-5-硝基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 13.0h， 以66%的产率得到(±)-4-(2-chloro-5-nitrophenyl)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-3,4-dihydro-2(1H)-pyridone
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012
• 作为产物：
  描述：

  3-羟基丙腈 、 1,3-dioxin-4-one 以 甲苯 为溶剂， 反应 24.0h， 以95%的产率得到2-cyanoethyl 2-oxobutanoate
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012

文献信息

• [EN] DIHYDROPYRIDINES AND NEW USES THEREOF<br/>[FR] DIHYDROPYRIDINES ET LEURS NOUVELLES UTILISATIONS
  申请人：——

  公开号：WO1994022829A2

  公开（公告）日：1994-10-13

  [EN] The invention provides a method of treating benign prostatic hyperplasia in a subject which comprises administering to the subject a therapeutically effective amount of a compound having structure (I) wherein Y is -(CH2)n-, where n is 1, 2, 3, 4 or 5; -(CH2)h-O-(CH2)k-, where h and k are independently the same or different and are 2, 3 or 4; -(CH2)h-CH=CH-(CH2)k-; or -(CH2)h-CC-(CH2)k-, where h and k are independently the same or different and are 1, 2, 3 or 4; wherein Z is 0, NH, or CH2; wherein R<1> is a linear or branched chain alkyl, alkoxyalkyl or arylalkyl group; wherein R<2> and R<4> are independently the same or different and are H, or a linear or branched chain alkyl group; wherein R<3> is H, a linear or branched chain alkyl, alkoxy, alkoxyalkyl or acyl group; and wherein R<5> and R<6> are independently the same or different and are H, OH, Cl, Br, F, No2, CN, CF3, or NH2, or a linear or branched chain alkyl, alkoxy, alkoxycarbonyl, acyl, alkylsulfoxide, alkylsulfone, or mono- or dialkylamino group. Other active compounds containing one, two or three rings are also disclosed as well as pharmaceutical compositions prepared therefrom and methods of use in the treatment of BPH, inhibition of cholesterol synthesis, and reduction of intraocular pressure.
  [FR] Méthode de traitement de l'hyperplasie prostatique bénigne par administration d'une dose à effet thérapeutique d'un composé de structure (I), où Y représente -(CH2)n- où n est égal à 1, 2, 3, 4 ou 5; -(CH2)h-O-(CH2)k, où h et k sont indépendamment identiques ou différents et égaux à 2, 3 ou 4; -(CH2)h-CH=CH-(CH2)k; ou -(CH2)h-CC-(CH2)k- où h et k sont indépendamment identiques ou différents et égaux à 1, 2, 3, ou 4; où Z représente O, NH ou CH2; où R1 représente un groupe alkyle, alcoxyalkyle ou arylalkyle linéaire ou à chaîne ramifiée; où R2 et R4 sont indépendamment identiques ou différents et représentent H ou un groupe alkyle linéaire ou à chaîne ramifiée; où R3 représente H, un groupe alkyle, alcoxy, alcoxyalkyle ou acyle linéaire ou à chaîne ramifiée; où R5 et R6 sont indépendamment identiques ou différents et représentent H, OH, Cl, Br, F, HO2, CN, CF3 ou NH2, ou un groupe alkyle, alcoxy, alcoxycarbonyle, acyle, alkylsulfoxyde, alkylsulfone linéaire ou à chaîne ramifiée, ou un groupe mono ou dialkylamino. D'autres composés actifs à un, deux, ou trois cycles sont également présentés ainsi que des préparations pharmaceutiques les contenant et leurs procédés d'utilisation dans le traitement de l'HPB, l'inhibition de la synthèse du cholestérol, et la réduction de la pression intraoculaire.
• Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives
  作者：Susana Y. Torres、Estael Ochoa、Yamila Verdecia、Francisca Rebolledo

  DOI：10.1016/j.tet.2014.05.012

  日期：2014.8

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.