Glyoxylsaeure-pyrrolidid | 106435-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: Glyoxylsaeure-pyrrolidid
• 英文别名: 1-(1,2-dioxoethyl)pyrrolidine；glyoxylic acid pyrrolidide；oxo-(1-pyrrolidinyl)acetaldehyde；N-glyoxyloylpyrrolidine；2-Oxo-2-pyrrolidin-1-ylacetaldehyde
• CAS: 106435-93-2
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: YJKBDXXDMRACHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  70-72 °C(Press: 0.05 Torr)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Glyoxylsaeure-pyrrolidid 在 palladium on activated charcoal 氢气 、 3-苄基羟乙基甲基噻唑氯化锂 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 6.17h， 生成 5-benzoyl-4-benzyl-1-(2-hydroxyethyl)-2-(pyrrolidinyl-1-carbonyl)-3b,4,5,6,6a,7-hexahydro-1H-1,5-diazacyclopenta[a]pentalene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Heterocyclic α-Alkylidene Cyclopentenones Obtained via a Pauson−Khand Reaction of Amino Acid Derived Allenynes. A Scope and Limitation Study Directed toward the Preparation of a Tricyclic Pyrrole Library

  摘要：

  [GRAPHICS]The synthesis of a novel class of tricyclic pyrroles has been accomplished by using a Pauson-Khand/Stetter/Paal-Knorr reaction sequence. Full details of the Pauson-Khand reaction of amino acid tethered allenynes 4a-e and 9a-d are disclosed. The study of this reaction led to the discovery of an unprecedented substituent effect on the diastereoselectivity of the MO(CO)(6) mediated allenic Pauson-Khand reaction. It was found that amino acid tethered allenynes with aromatic side chains afford alpha-alkylidene cyclopentenones with the opposite diastereoselectivity compared to those with aliphatic side chains. This effect has been attributed to complexation of the metal mediator to the aromatic ring in the substrate. Furthermore, an isomerization of one of the diastereomers of the a-alkylidene cyclopentenones was encountered, leading to eventual decomposition. The stable diastereomers were found to react well in the Stetter reaction leading to 1,4-diketones that were converted to pyrroles. The observation that the first generation of 2-alkyl-substituted pyrroles was unstable led to a second generation of 2-carboxamide pyrroles with sufficient stability for biological tests which are in progress.

  DOI：

  10.1021/jo0481607
• 作为产物：
  描述：

  1-(1-吡咯烷基)-2-丙烯-1-酮 在 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Glyoxylsaeure-pyrrolidid
  参考文献：
  名称：

  One-Pot Condensation-Oxidation of Glyoxamide with 1,2-Diamines Providing Imidazolines and Benzimidazoles

  摘要：

  描述了一种新方法，用于合成在2位具有酰胺的咪唑啉和苯并咪唑。研究发现，醛酰胺与脂肪族和芳香族1,2-二胺反应，可以通过一步凝聚-氧化程序形成五元环咪唑啉和苯并咪唑。

  DOI：

  10.1055/s-0029-1217120

文献信息

• CYCLOALKYLCARBAMATE BENZAMIDE ANILINE HDAC INHIBITOR COMPOUNDS
  申请人：Venkataramani Chandrasekar

  公开号：US20100311794A1

  公开（公告）日：2010-12-09

  The present invention provides a compound of general Formula (I) having histone deacetylase (HDAC) inhibitory activity, a pharmaceutical composition comprising the compound, and a method useful to treat diseases using the compound.

  本发明提供了一种具有组蛋白去乙酰化酶（HDAC）抑制活性的一般式（I）化合物，包括该化合物的药物组合物，以及使用该化合物治疗疾病的方法。
• [EN] INDOLYLMETHYL-MORPHOLINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DERIVES D'INDOLYLMETHYL-MORPHOLINE EN TANT QU'INHIBITEURS DES KINASES
  申请人：UCB PHARMA SA

  公开号：WO2010146351A1

  公开（公告）日：2010-12-23

  A series of morpholine derivatives, substituted in the 4-position by a substituted carbonyl or sulfonyl moiety, and in the 3-position by an optionally substituted indol-3-ylmethyl group, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列在4-位置被取代的吗啉衍生物，通过取代的羰基或磺酰基团取代，并在3-位置通过一个可选择取代的吲哚-3-基甲基基团，作为选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病方面。
• Preparation of 3-benzoylpenems and penem amides by wittig methodology
  作者：Neil D Pearson、Terence C Smale、Robert Southgate

  DOI：10.1016/0040-4039(95)00767-7

  日期：1995.6

  Condensation of phenyl glyoxal with azetidin-2-ones (1a-c) gave the hemi-aminals (2a-c). Subsequent conversions produced the 4-(formylthio)phosphoranes (4a-c) which gave on heating the 3-benzoylpenems (5a-c), formed by intramolecular Wittig cyclisation. Thermal isomerisation of trans-6-substituted-3-benzoylpenems allowed the preparation of the cis-6-substituted-3-benzoylpenems (7a-c). Using similar

  苯乙二醛与氮杂环丁烷-2-酮（1a-c）的缩合得到半缩醛（2a-c）。随后的转化产生了4-（甲硫基）膦酸酯（4a-c），其通过加热通过分子内维蒂希环化形成了3-苯甲酰基penems（5a-c）。反式-6取代的-3-苯甲酰基青霉烯的热异构化允许制备顺式-6取代的-3-苯甲酰基青霉烯（7a-c）。使用相似的方法，合成了戊烯酰胺（7d-e）。
• 6-(1-carbamoyl-1-hydroxymethyl)penicillanic acid derivatives
  申请人：Pfizer Inc.

  公开号：US04797394A1

  公开（公告）日：1989-01-10

  6-(1-Carbamoyl-1-hydroxymethyl)penicillanic acid derivatives are useful as antibacterials and/or beta-lactamase inhibitors.

  6-(1-氨甲酰基-1-羟甲基)青霉烷酸衍生物可用作抗菌剂和/或β-内酰胺酶抑制剂。
• [EN] SUBSTITUTED ARYLSULFONYLAMINOMETHYLPHOSPHONIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF TYPE I AND II DIABETES MELLITUS<br/>[FR] DÉRIVÉS SUBSTITUÉS DE L'ACIDE ARYLSULFONYLAMINOMÉTHYLPHOSPHONIQUE, LEUR PRÉPARATION ET LEUR UTILISATION POUR TRAITER LE DIABÈTE SUCRÉ DE TYPE I ET DE TYPE II
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009016119A1

  公开（公告）日：2009-02-05

  The present invention relates to substituted arylsulphonylaminomethylphosphonic acid derivatives of general formula (I) wherein R, X, Y and Z are defined as in claim 1, the tautomers, enantiomers, diastereomers, mixtures thereof and salts thereof which have valuable pharmacological properties, particularly the suppression of the interaction of glycogen phosphorylase a with the GL subunit of glycogen-associated protein phosphatase 1 (PP1), and their use as pharmaceutical compositions.

  本发明涉及一般式(I)的取代芳基磺酰氨甲基膦酸衍生物，其中R、X、Y和Z如权利要求书中所定义，其互变异构体、对映体、非对映体、它们的混合物及其盐具有有价值的药理特性，特别是抑制糖原磷酸化酶a与糖原相关蛋白磷酸酶1（PP1）的GL亚基的相互作用，并将其用作药物组成物。