3-[(benzyloxy)methyl]hex-5-enal | 1160960-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(benzyloxy)methyl]hex-5-enal
• 英文别名: 3-(Phenylmethoxymethyl)hex-5-enal
• CAS: 1160960-87-1
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: XKAVZDMZDDRSRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(benzyloxy)methyl]hex-5-enal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 0.25h， 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：

  4-carbomethoxy-6-t-butyldimethylsiloxy-1-hexene 在 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 3-[(benzyloxy)methyl]hex-5-enal
  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

文献信息

• DABO Boronate Promoted Conjugate Allylation of α,β-Unsaturated Aldehydes Using Copper(II) Catalysis
  作者：Pjotr C. Roest、Nicholas W. M. Michel、Robert A. Batey

  DOI：10.1021/acs.joc.6b00782

  日期：2016.8.5

  method for the selective 1,4-conjugate allylation of α,β-unsaturated aldehydes is reported. The method employs an air-stable diethanolamine-complexed boronic acid (DABO boronate) as the allyl transfer reagent and promotes conjugate addition over 1,2-addition. A variety of aryl- and alkyl-substituted enals are tolerated, providing δ,ε-unsaturated aldehyde products in good yields and selectivities under mild

  报道了用于α，β-不饱和醛的选择性1，4-共轭烯丙基化的第一种催化方法。该方法采用空气稳定的二乙醇胺复合硼酸（DABO硼酸酯）作为烯丙基转移剂，并通过1,2-加成促进共轭物的添加。可以耐受多种被芳基和烷基取代的烯醛，可在温和条件下以高收率和选择性提供δ，ε-不饱和醛产物。