(E)-4-hydroxy-3-methylbut-3-en-2-one sodium salt | 132247-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-hydroxy-3-methylbut-3-en-2-one sodium salt
• 英文别名: 3-formyl-2-butanone sodium salt；2-methyl-3-oxobutanal sodium salt；sodium (1E)-2-methyl-3-oxobut-1-en-1-olate；2-methyl-3-oxobutanal sodium；sodium;(E)-2-methyl-3-oxobut-1-en-1-olate
• CAS: 132247-74-6
• 化学式: C₅H₇O₂*Na
• 分子量: 122.099
• InChiKey: VZUJKSCAQOORQX-BJILWQEISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.16
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-3-methylbut-3-en-2-one sodium salt 在 盐酸 、 水 、 哌啶乙酸盐 作用下， 反应 93.25h， 生成 5,6-二甲基-1H-吡啶-2-酮
  参考文献：
  名称：

  2-PYRIDONE DERIVATIVES HAVING AFFINITY FOR CANNABINOID TYPE 2 RECEPTOR

  摘要：

  公开号：

  EP1357111B1
• 作为产物：
  描述：

  丁酮 生成 (E)-4-hydroxy-3-methylbut-3-en-2-one sodium salt
  参考文献：
  名称：

  US6063782A

  摘要：

  公开号：

文献信息

• Practical radical cyclisations leading to the construction of near-stereopure quaternary carbon stereogenic centres
  作者：Raymond McCague、Robin G. Pritchard、Richard J. Stoodley、Douglas S. Williamson

  DOI：10.1039/a807930g

  日期：——

  The 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl auxiliary is effective in directing bromopropargyloxy additions to the olefinic bonds of vinylogous esters/carbonates; in the presence of AIBN and 1-ethylpiperidinium hypophosphite, the adducts undergo highly stereoselective reductive radical cyclisations in which quaternary carbon stereogenic centres are generated.

  2,3,4,6-四-O-乙酰基-β-D-吡喃葡糖苷辅助基团在指导溴炔氧加成到乙烯类酯/碳酸酯的烯烃键上非常有效；在AIBN和1-乙基哌啶醇次磷酸盐的存在下，加成产物经历了高度立体选择性的还原自由基环化反应，其中生成了四级碳立体中心。
• [EN] PYRIDINE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR TREATING DISEASES RELATED TO MCH RECEPTOR<br/>[FR] DERIVES DE PYRIDINE ET LEUR UTILISATION EN TANT QUE MEDICAMENTS POUR LE TRAITEMENT DES MALADIES LIEES AUX RECEPTEURS MCH
  申请人：TAISHO PHARMA CO LTD

  公开号：WO2006035967A1

  公开（公告）日：2006-04-06

  The present invention encompasses novel substituted pyridine compounds of Formula (I), which act as MCH receptor antagonists. These compositions and pharmaceutical compositions thereof are useful in the prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.

  本发明涵盖了化学式（I）的新型取代吡啶化合物，其作为MCH受体拮抗剂。这些组合物及其药物组合物在预防或治疗改善记忆功能、睡眠和觉醒、焦虑、抑郁、情绪障碍、癫痫、肥胖、糖尿病、食欲和进食障碍、心血管疾病、高血压、血脂异常、心肌梗死、暴饮暴食障碍包括暴食症、厌食症、精神障碍包括躁郁症、精神分裂症、谵妄、痴呆、压力、认知障碍、注意力缺陷障碍、物质滥用障碍和运动障碍包括帕金森病、癫痫和成瘾症方面具有用处。
• Diastereoselective hydrogenations of α-alkyl α-(2,3,4,6-tetra-O-acetyl-β-<scp>D</scp>-glucopyranosyloxy)methylene carbonyl compounds. New route to stereopure α-alkyl α-oxymethyl carbonyl compounds
  作者：David S. Larsen、Anthony Schofield、Richard J. Stoodley、Peter D. Tiffin

  DOI：10.1039/p19960002487

  日期：——

  Wittig condensation of the stabilised phosphoranes 9, 10 and 26 with 1-formyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 11 leads to the vinylogous carbonates 12, 13 and 22. The salts 27–30 and 44, prepared from the corresponding carbonyl compounds, ethyl formate and sodium methoxide, react with acetobromoglucose 21 to give compounds 22–25 and 43.

  稳定的膦烷9、10和26与1-甲酰基-2,3,4,6-四-O-乙酰基-β - D-吡喃葡萄糖11的维蒂希缩合产生碳酸乙烯基酯12、13和22。盐27由相应的羰基化合物，甲酸乙酯和甲醇钠制备的–30和44，与乙酰溴葡萄糖21反应，得到化合物22–25和43。
• Regio- and stereo-selective bromo(alkoxylation)s of (E )-α-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethylene) carbonyl compounds. A route to near-stereopure α-bromo α-dioxymethyl carbonyl compounds †
  作者：M. Sum Idris、David S. Larsen、Robin G. Pritchard、Anthony Schofield、Richard J. Stoodley、Peter D. Tiffin

  DOI：10.1039/b002749i

  日期：——

  (E)-4-Methoxymethoxy-3-methylbut-3-en-2-one 17b reacts with NBS in propan-1-ol in a highly regio- and anti-stereo-selective manner to give (3R*,4R*)-3-bromo-4-methoxymethoxy-3-methyl-4-propoxybutan-2-one 18. Compound 10, a relative of the butenone 17b in which the methoxymethyl group is replaced by the 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl unit, undergoes an analogous bromo(propoxylation) reaction with reasonable facial selectivity to give an 86∶14 mixture of (3R,4R)-3-bromo-3-methyl-4-propoxy-4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyloxy)butan-2-one 11c and its (3S,4S)-diastereomer 12c. The major bromo(propoxy) derivative, isolable in 57% yield by fractional crystallisation, is assigned the stereostructure 11c by single-crystal X-ray crystallographic analysis. Other primary alcohols and methanol participate in the reaction of compound 10 with NBS, leading predominantly (with selectivities ranging from 75∶25 to 89∶11) to bromo(alkoxy) products of type 11 which are usually separable from their diastereomers of type 12 by fractional crystallisation (in yields ranging from 41 to 64%). A model to account for the role of the 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl unit in the stereoinduction process is proposed. Related bromo(propoxylation)s are observed with the vinylogous esters 24, 25a and 25b, leading to the isolation of the major products, 28, 30a and 30b (in yields ranging from 39 to 55%), and with the vinylogous carbonates 32a, 32c, 37a and 37b, providing access to the major products 33a, 33c, 38a and 38b (in yields ranging from 52 to 73%). In the presence of trifluoroacetic acid and ethane-1,2-diol, the bromo(propoxy) derivatives 11c, 28, 30b and 33c undergo transacetalisation to give the ethylene glycol acetals 40a, 40b, 41 and 40c with ees of 94–98%, in yields ranging from 56 to 67%. p

  (E)-4-甲氧基甲氧基-3-甲基丁-3-烯-2-酮 17b 在丙-1-醇中与 NBS 反应，以高度的区域选择性和反式立体选择性方式生成 (3R*,4R*)-3-溴-4-甲氧基甲氧基-3-甲基-4-丙氧基丁-2-酮 18。化合物 10 是丁烯酮 17b 的类似物，其中甲氧基甲基被 2,3,4,6-四-O-乙酰基-β-D-吡喃葡糖基单元取代，在适当的面对选择性下经历类似的溴（丙氧基化）反应，得到 (3R,4R)-3-溴-3-甲基-4-丙氧基-4-(2′,3′,4′,6′-四-O-乙酰基-β-D-吡喃葡糖氧基)丁-2-酮 11c 和其 (3S,4S) 非对映异构体 12c 的 86∶14 混合物。主要溴（丙氧基）衍生物通过分步结晶可分离得到 57% 产率，并通过单晶 X 射线晶体学分析确定其立体结构为 11c。其他一级醇和甲醇参与化合物 10 与 NBS 的反应，主要生成类型 11 的溴（烷氧基）产物，通常可通过分步结晶从类型 12 的非对映异构体中分离（产率范围为 41% 至 64%），选择性从 75∶25 到 89∶11 不等。提出了一个模型来解释 2,3,4,6-四-O-乙酰基-β-D-吡喃葡糖基单元在立体诱导过程中的作用。类似的溴（丙氧基化）反应在乙烯基酯 24、25a 和 25b 中也观察到，主要产物 28、30a 和 30b 被分离（产率范围为 39% 至 55%），乙烯基碳酸酯 32a、32c、37a 和 37b 也观察到类似反应，主要产物 33a、33c、38a 和 38b 被分离（产率范围为 52% 至 73%）。 在三氟乙酸和乙二醇存在下，溴（丙氧基）衍生物 11c、28、30b 和 33c 经历转缩醛反应，生成乙二醇缩酮 40a、40b、41 和 40c，对映体过量为 94% 至 98%，产率范围为 56% 至 67%。
• Asymmetric Diels–Alder reactions. Part 5. Influence of sugar substituents upon the diastereofacial reactivity of (E-)3-(t-butyldimethylsiloxy)-1-(<scp>D</scp>-glucopyranosyloxy)buta-1,3-dienes
  作者：Brian Beagley、David S. Larsen、Robin G. Pritchard、Richard J. Stoodley

  DOI：10.1039/p19900003113

  日期：——

  1-(3′,4′,6′-tri-O-acetyl-2′-deoxy-α-D-glucopyranosyloxy), and 1-(2′,3′,4′-tri-O-acetyl-α-D-xylopyranosyloxy) derivatives of (E-)3-(t-butyldimethylsiloxy)buta-1,3-diene, i.e.(6d-g), and their β-anomers, i.e.(11c-f), have been prepared and their diastereofacial reactivities towards N-phenylmaleimide assessed. Whereas the 2′-O-(t-butyldimethylsilyl)-α-diene (6d) gave a 20 : 80 mixture of thecycloadducts

  1- [3'，4'，6'-tn-O-乙酰基-2'- O-（叔丁基二甲基甲硅烷基）-α- D-吡喃葡萄糖基氧基]，1- [2，'，3'，4'-三-O-乙酰基-6'- O-（叔丁基二甲基甲硅烷基）-α- D-吡喃葡萄糖基氧基]，1-（3'，4'，6'-三-O-乙酰基-2'-脱氧-α- D（E-）3-（叔丁基二甲基甲硅烷氧基）buta-1,3-diene的1-（2'，3'，4'-三-O-乙酰基-α - D-吡喃吡喃糖基氧基）衍生物和即（6d - g）及其β-端异构体，即（11c - f），已制备，并评估了它们对N-苯基马来酰亚胺的非对面反应性。而2' - O-（叔丁基二甲基甲硅烷基）-α-二烯（6d）给出了环加合物（9d）和（10d）的20:80混合物，其β-异头物即（11c）得到66:34环加合物（12c）和（13c）的混合物[具有（1 R，2 R，3 S）构型的主要环加合物]。6' - O-