2-(2-Hydroxy-ethyl)-pent-4-enoic acid methyl ester | 123453-81-6

• 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-(2-Hydroxy-ethyl)-pent-4-enoic acid methyl ester
• 英文别名: Methyl 2-(2-hydroxyethyl)pent-4-enoate
• CAS: 123453-81-6
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: UKPSTQNNYIENFA-UHFFFAOYSA-N

物化性质

• 沸点：
  233.6±33.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-Hydroxy-ethyl)-pent-4-enoic acid methyl ester 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 hexanes 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 21.75h， 生成 dimethyl 6-((benzyloxy)methyl)oct-3-enedioate
  参考文献：
  名称：

  Discovery of LFF571: An Investigational Agent for Clostridium difficile Infection

  摘要：

  Clostridium difficile (C. difficile) is a Gram positive, anaerobic bacterium that infects the lumen of the large intestine and produces toxins. This results in a range of syndromes from mild diarrhea to severe toxic megacolon and death. Alarmingly, the prevalence and severity of C. difficile infection are increasing; thus, associated morbidity and mortality rates are rising. 4-Aminothiazolyl analogues of the antibiotic natural product GE2270 A (1) were designed, synthesized, and optimized for the treatment of C. difficile infection. The medicinal chemistry effort focused on enhancing aqueous solubility relative to that of the natural product and previous development candidates (2, 3) and improving antibacterial activity. Structure-activity relationships, cocrystallographic interactions, pharmacokinetics, and efficacy in animal models of infection were characterized. These studies identified a series of dicarboxylic acid derivatives, which enhanced solubility/efficacy profile by several orders of magnitude compared to previously studied compounds and led to the selection of LFF571 (4) as an investigational new drug for treating C. difficile infection.

  DOI：

  10.1021/jm201685h
• 作为产物：
  描述：

  3-allyldihydrofuran-2-one 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.75h， 生成 2-(2-Hydroxy-ethyl)-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Trost, Barry M.; Moeller, Kevin D., Heterocycles, 1989, vol. 28, # 1, p. 321 - 331

  摘要：

  DOI：

文献信息

• Ni-catalyzed two-component reductive dicarbofunctionalization of alkenes <i>via</i> radical cyclization
  作者：Yulong Kuang、Xuefeng Wang、David Anthony、Tianning Diao

  DOI：10.1039/c8cc00358k

  日期：——

  A reductive dicarbofunctionalization reaction of alkenes has been developed and applied to the preparation of substituted carbo- and heterocycles. The reaction conditions avoid the use of air-sensitive organometallic reagents, and are compatible with a broad range of bromo-electrophiles and a wide variety of substituents to give cyclic products in excellent yields.

  已经开发了烯烃的还原性双碳官能化反应，并将其用于制备取代的碳环和杂环。反应条件避免了使用对空气敏感的有机金属试剂，并且可与各种溴亲电子试剂和各种取代基兼容，从而以优异的收率得到环状产物。
• AMINOTHIAZOLES AND THEIR USES
  申请人：Bushell Simon

  公开号：US20170015704A1

  公开（公告）日：2017-01-19

  The present application describes organic compounds of Formula (I) and pharmaceutical compositions thereof, and their use for the treatment, prevention and/or amelioration of diseases, particularly bacterial infections.
• US4260552A
  申请人：——

  公开号：US4260552A

  公开（公告）日：1981-04-07
• Discovery of LFF571: An Investigational Agent for <i>Clostridium difficile</i> Infection
  作者：Matthew J. LaMarche、Jennifer A. Leeds、Adam Amaral、Jason T. Brewer、Simon M. Bushell、Gejing Deng、Janetta M. Dewhurst、Jian Ding、JoAnne Dzink-Fox、Gabriel Gamber、Akash Jain、Kwangho Lee、Lac Lee、Troy Lister、David McKenney、Steve Mullin、Colin Osborne、Deborah Palestrant、Michael A. Patane、Elin M. Rann、Meena Sachdeva、Jian Shao、Stacey Tiamfook、Anna Trzasko、Lewis Whitehead、Aregahegn Yifru、Donghui Yu、Wanlin Yan、Qingming Zhu

  DOI：10.1021/jm201685h

  日期：2012.3.8

  Clostridium difficile (C. difficile) is a Gram positive, anaerobic bacterium that infects the lumen of the large intestine and produces toxins. This results in a range of syndromes from mild diarrhea to severe toxic megacolon and death. Alarmingly, the prevalence and severity of C. difficile infection are increasing; thus, associated morbidity and mortality rates are rising. 4-Aminothiazolyl analogues of the antibiotic natural product GE2270 A (1) were designed, synthesized, and optimized for the treatment of C. difficile infection. The medicinal chemistry effort focused on enhancing aqueous solubility relative to that of the natural product and previous development candidates (2, 3) and improving antibacterial activity. Structure-activity relationships, cocrystallographic interactions, pharmacokinetics, and efficacy in animal models of infection were characterized. These studies identified a series of dicarboxylic acid derivatives, which enhanced solubility/efficacy profile by several orders of magnitude compared to previously studied compounds and led to the selection of LFF571 (4) as an investigational new drug for treating C. difficile infection.
• Trost, Barry M.; Moeller, Kevin D., Heterocycles, 1989, vol. 28, # 1, p. 321 - 331
  作者：Trost, Barry M.、Moeller, Kevin D.

  DOI：——

  日期：——