2-sec-Butyl-5-hexenoic acid | 147120-61-4

• 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-sec-Butyl-5-hexenoic acid
• 英文别名: 2-butan-2-ylhex-5-enoic acid
• CAS: 147120-61-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: XZNYJCZQTOSJBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-sec-Butyl-5-hexenoic acid 在 溴 作用下， 以 乙醚 为溶剂， 生成 5,6-Dibromo-2-sec-butyl-hexanoic acid
  参考文献：
  名称：

  New approaches to the synthesis of alkyl-substituted enol lactone systems, inhibitors of the serine protease elastase

  摘要：

  We have synthesized a series of alkyl-substituted enol lactones designed to act as mechanism-based inhibitors of human neutrophil elastase (HLE). General methods were developed for the preparation of alpha- and beta-alkyl-substituted 5-hexynoic acids by the bromoform reaction on the corresponding alkynoic methyl ketone, prepared by an Eschenmoser-Tanabe fragmentation sequence from a suitably substituted cyclohexenone. By this method, beta-methyl- and beta,beta-dimethyl-5-hexynoic acids were synthesized from commercially available isophorone and 3,5-dimethyl-2-cyclohexen-1-one, respectively. Alpha-Substituted 5-hexynoic acids were prepared from 3-ethoxy-2-cyclohexen-1-one, using a novel ZnCl2-mediated alkylation that we developed; this method gives high yields of alpha'-alkylation products, even with secondary halides. The most efficient method for the preparation of alpha-substituted 5-hexynoic acids involved a four-reaction sequence-alkylation of the alpha-substituted ester with 1,4-dibromobutane, elimination, bromination and bisdehydrobromination-that proceeded in high overall yield. Protio enol lactonizations were performed with mercury(II) catalysis in CH2Cl2 or CH2Cl2-H2O. Stereo-selective Z-bromo enol lactonization was carried out by Br+-induced lactonization in the presence of Ag+. E-Bromo enol lactonization with N-bromosuccinimide in CH2Cl2 in the presence of a small amount of water gave better yields and shorter reaction times than the traditional anhydrous conditions. In studies of the inhibitory activity of these lactones toward several proteases (reported in full elsewhere), we found that the alpha-alkyl-substituted protio and bromo enol lactones 1-3 were very good inhibitors of HLE, with k(a)/K(i) values ranging from 14 500 to 37 500 M-1 s-1; the beta-alkyl-substituted enol lactones 5-8 showed only moderate inhibition of HLE.

  DOI：

  10.1021/jo00059a049
• 作为产物：
  描述：

  Ethyl 6-bromo-2-sec-butylhexanoate 在 氢氧化钾 、 potassium tert-butylate 、 水 作用下， 生成 2-sec-Butyl-5-hexenoic acid
  参考文献：
  名称：

  New approaches to the synthesis of alkyl-substituted enol lactone systems, inhibitors of the serine protease elastase

  摘要：

  We have synthesized a series of alkyl-substituted enol lactones designed to act as mechanism-based inhibitors of human neutrophil elastase (HLE). General methods were developed for the preparation of alpha- and beta-alkyl-substituted 5-hexynoic acids by the bromoform reaction on the corresponding alkynoic methyl ketone, prepared by an Eschenmoser-Tanabe fragmentation sequence from a suitably substituted cyclohexenone. By this method, beta-methyl- and beta,beta-dimethyl-5-hexynoic acids were synthesized from commercially available isophorone and 3,5-dimethyl-2-cyclohexen-1-one, respectively. Alpha-Substituted 5-hexynoic acids were prepared from 3-ethoxy-2-cyclohexen-1-one, using a novel ZnCl2-mediated alkylation that we developed; this method gives high yields of alpha'-alkylation products, even with secondary halides. The most efficient method for the preparation of alpha-substituted 5-hexynoic acids involved a four-reaction sequence-alkylation of the alpha-substituted ester with 1,4-dibromobutane, elimination, bromination and bisdehydrobromination-that proceeded in high overall yield. Protio enol lactonizations were performed with mercury(II) catalysis in CH2Cl2 or CH2Cl2-H2O. Stereo-selective Z-bromo enol lactonization was carried out by Br+-induced lactonization in the presence of Ag+. E-Bromo enol lactonization with N-bromosuccinimide in CH2Cl2 in the presence of a small amount of water gave better yields and shorter reaction times than the traditional anhydrous conditions. In studies of the inhibitory activity of these lactones toward several proteases (reported in full elsewhere), we found that the alpha-alkyl-substituted protio and bromo enol lactones 1-3 were very good inhibitors of HLE, with k(a)/K(i) values ranging from 14 500 to 37 500 M-1 s-1; the beta-alkyl-substituted enol lactones 5-8 showed only moderate inhibition of HLE.

  DOI：

  10.1021/jo00059a049

文献信息

• COPOLYMER OF OLEFIN AND UNSATURATED CARBOXYLIC ACID OR UNSATURATED CARBOXYLIC ACID DERIVATIVE
  申请人：China Petroleum & Chemical Corporation

  公开号：EP3702381A1

  公开（公告）日：2020-09-02

  The present invention provides a copolymer of an olefin and an unsaturated carboxylic acid or an unsaturated carboxylic acid derivative, said copolymer being a spherical and/or spherical-like polymer. The copolymer provided by the invention exhibits a good morphology and has good prospects in industrial use.

  本发明提供了一种烯烃与不饱和羧酸或不饱和羧酸衍生物的共聚物，所述共聚物为球形和/或类球形聚合物。本发明提供的共聚物具有良好的形态，在工业应用中具有良好的前景。
• [EN] METHOD FOR PREPARING OLEFIN-POLAR MONOMER COPOLYMER<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COPOLYMÈRE DE MONOMÈRE POLAIRE D'OLÉFINE<br/>[ZH] 用于制备烯烃-极性单体共聚物的方法
  申请人：[en]CHINA PETROLEUM & CHEMICAL CORPORATION;[zh]中国石油化工股份有限公司

  公开号：WO2021083358A1

  公开（公告）日：2021-05-06

  一种用于制备烯烃-烯烃醇共聚物的方法及由所述方法制备的烯烃-烯烃醇共聚物。所述用于制备烯烃-烯烃醇共聚物的方法中使用的催化剂包含式I所示的二亚胺金属配合物。根据制备方法的优选实施方式制得的球形和/或类球形聚合物在工业应用中具有良好的前景。
• METHOD FOR PREPARING OLEFIN-POLAR MONOMER COPOLYMER
  申请人：CHINA PETROLEUM & CHEMICAL CORPORATION

  公开号：US20220396646A1

  公开（公告）日：2022-12-15

  A method for preparing an olefin-olefinic alcohol copolymer and an olefin-olefinic alcohol copolymer prepared by the method are provided. The catalyst used in the method for preparing the olefin-olefinic alcohol copolymer has a diimine metal complex as shown in Formula I.