4-Acetamidobutyraldehyde Diethyl Acetal | 68029-07-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Acetamidobutyraldehyde Diethyl Acetal
• 英文别名: N-(4,4-diethoxybutyl) acetamide；N-(4,4-diethoxybutyl)acetamide；1-acetamido-4,4-diethoxybutane；4-(N-acetylamino)butyraldehyde-diethylacetal；4-Acetamino-1.1-diethoxy-butan
• CAS: 68029-07-2
• 化学式: C₁₀H₂₁NO₃
• mdl: MFCD24388794
• 分子量: 203.282
• InChiKey: ANONYJUYWUFMOA-UHFFFAOYSA-N

物化性质

• 沸点：
  115-118 °C(Press: 0.03 Torr)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Acetamidobutyraldehyde Diethyl Acetal 在 10% palladium on activated carbon 、 氢气 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~60.0 ℃ 、300.01 kPa 条件下， 反应 6.0h， 生成 trans-N-{3-[5-(4-cyclopentyloxyphenoxy)[1,3]dioxan-2-yl]propyl}acetamide
  参考文献：
  名称：

  Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation

  摘要：

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.

  DOI：

  10.1021/jm101179e
• 作为产物：
  描述：

  4-氨基丁醛缩二乙醇 在 乙酸酐 作用下， 反应 1.0h， 生成 4-Acetamidobutyraldehyde Diethyl Acetal
  参考文献：
  名称：

  7-氟和6,7-二氟血清素与7-氟和6,7-二氟褪黑激素的合成

  摘要：

  Fischer吲哚合成的Abramovitch适应性降低了7-氟-5-甲氧基色胺的收率，这部分归因于所需脱羧步骤中的分解。因此，通过氨基丁醛（由二乙缩醛原位生成）与2-氟和2,3-二氟-4-甲氧基苯基肼反应，制得7-氟和6,7-二氟-5-甲氧基色胺。转换为相应的5-羟色胺。褪黑素是通过一锅反应制备的，该反应涉及氨基丁醛的原位乙酰化。

  DOI：

  10.1016/j.jfluchem.2006.06.015

文献信息

• 4-substituted 2-aminoalk-3-enoic acids
  申请人：Ciba-Geigy Corp.

  公开号：US05294734A1

  公开（公告）日：1994-03-15

  Substituted 2-aminoalk-3-enoic acid derivative of formula I ##STR1## wherein R.sub.1 is an aliphatic hydrocarbon radical that is substituted by optionally acylated or aliphatically or araliphatically etherified hydroxy, by halogen, by optionally acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxa-cycloaliphatic radical, or is an oxacycloaliphatic hydrocarbon radical bonded via a carbon atom, or is an optionally aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical, and R.sub.2 is free or esterified carboxy, and their salts exhibit NMDA-antagonistic properties and are useful as active ingredients of anticonvulsive medicaments.

  取代的2-氨基烷基-3-烯酸衍生物的公式I ##STR1## 其中R.sub.1是一个被取代的脂肪烃基团，可以通过选择性地酰化或脂肪族或芳脂肪族醚化的羟基，通过卤素，通过选择性地酰化和/或脂肪族取代的氨基，或者通过一个aza-，diaza-，azoxa-或oxa-环脂肪族基团，或者是一个通过碳原子连接的氧杂环脂肪烃基团，或者是一个选择性地脂肪族N-取代或N-酰化的氮杂环脂肪烃基团，并且R.sub.2是自由的或酯化的羧基，它们的盐类具有NMDA-拮抗性质，并且作为抗惊厥药物的有效成分是有用的。
• Synthesis of 4- and 6-Azaindoles via the Fischer Reaction
  作者：Matthieu Jeanty、Jérôme Blu、Franck Suzenet、Gérald Guillaumet

  DOI：10.1021/ol902139r

  日期：2009.11.19

  Contrary to the common idea that Fischer indole cyclization often cannot be effectively applied to the synthesis of the corresponding azaindoles, we show that this approach can be actually very efficient for the formation of 4- and 6-azaindoles bearing an electron-donating group on the starting pyridylhydrazines. Two 4-azaindole natural product analogues were synthesized in a few steps and very good

  与通常认为Fischer吲哚环化通常不能有效地用于合成相应的氮杂吲哚的普遍观点相反，我们证明了这种方法实际上对于形成在其上带有给电子基团的4-和6-氮杂吲哚非常有效。起始吡啶基肼。通过几个步骤合成了两个4-氮杂吲哚天然产物类似物，并且具有很高的总收率。
• 1-N-alkyl-aminoglycoside-XK-88 derivatives and methods for their
  申请人：Schering Corporation

  公开号：US04002608A1

  公开（公告）日：1977-01-11

  1-N-Alkyl-Aminoglycoside-XK-88 derivatives, valuable as antibacterial agents, are prepared by the reaction of an acid addition salt of the corresponding 1-N-unsubstituted-Aminoglycoside-XK-88 antibacterial derivative or of a 2"-N-alkanoyl-Aminoglycoside-XK-88-5 derivative in an inert solvent, preferably a protic solvent containing water, with one equivalent of a hydride-donor reducing agent and with at least one equivalent of an aldehyde. The 2"-N-alkanoyl-Aminoglycoside-XK-88-5 intermediates are prepared by the reaction of a partially neutralized acid addition salt of Aminoglycoside-XK-88-5 with an acylating agent, and isolating the 2"-N-alkanoyl-Aminoglycoside-XK-88-5.

  1-N-烷基氨基糖苷-XK-88衍生物，作为抗菌剂具有很高的价值，通过将相应的1-N-未取代氨基糖苷-XK-88抗菌衍生物的酸加成盐或2"-N-烷酰氨基糖苷-XK-88-5衍生物在惰性溶剂中（最好是含水的质子溶剂）与一个当量的氢化剂还原剂和至少一个等量的醛反应来制备。2"-N-烷酰氨基糖苷-XK-88-5中间体通过将氨基糖苷-XK-88-5的部分中和酸加成盐与酰化剂反应，并分离出2"-N-烷酰氨基糖苷-XK-88-5来制备。
• 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, methods for their
  申请人：Schering Corporation

  公开号：US04002742A1

  公开（公告）日：1977-01-11

  1-N-Alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, valuable as antibacterial agents, are prepared by treating an acid addition salt of a 4,6-di-(aminoglycosyl)-1,3-diamonocyclitol antibacterial agent in an inert solvent, preferably a protic solvent containing water, with one equivalent of a hydride donor reducing agent and with at least one equivalent of an aldehyde. The 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols are also prepared by treating the corresponding 1-N-acyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitol with an amide-reducing hydride reagent in an inert organic solvent. Other methods of preparing 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols include carrying out the foregoing processes with partially N-protected intermediates. Another useful process involves preparing a Schiff base of the 1-amino function of a partially N-protected 4,6-di-(aminoglycosyl)-1,3-diaminocyclitol followed by reduction of said Schiff base and removal of the N-protecting groups. Pharmaceutical compositions comprising 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols are described as well as the method of using said compositions to elicit an antibacterial response in a warm blooded animal having a susceptible bacterial infection.

  1-N-烷基-4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇是一种有价值的抗菌剂，通过在惰性溶剂中处理4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇抗菌剂的酸盐，并与一个等当量的氢化物供体还原剂和至少一个等当量的醛反应来制备。也可以通过在惰性有机溶剂中使用酰胺还原氢化物试剂处理相应的1-N-酰基-4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇来制备1-N-烷基-4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇。制备1-N-烷基-4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇的其他方法包括使用部分N-保护中间体进行前述过程。另一种有用的方法涉及制备部分N-保护的4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇的1-氨基功能的席夫碱，随后还原所述席夫碱并去除N保护基团。还描述了包括1-N-烷基-4,6-二-(氨基糖苷基)-1,3-二氨基环糖醇的药物组合物，以及使用这些组合物在感染易感细菌的温血动物中引发抗菌反应的方法。
• Triflic acid-mediated phenylation of N-acylaminoalkyl diethylacetals and N-acyl-2-phenyl cyclic amides
  作者：Frank D. King、Stephen Caddick

  DOI：10.1039/c0ob01149e

  日期：——

  The reaction of N-acylaminoalkyl diethylacetals with triflic acid in benzene gave N-acylamino-diphenylalkyls. The proposed intermediates are the N-acyl-2-phenyl cyclic amides, which themselves are similarly converted to N-acylamino-diphenylalkyls.

  N-酰基氨基烷基二乙缩醛与三氟甲磺酸 在 苯得到N-酰基氨基-二苯基烷基。所提出的中间体是N-酰基-2-苯基环状酰胺，其本身被类似地转化为N-酰基氨基-二苯基烷基。