2'-methylpropyl 3-oxopropionate | 126101-13-1

• 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'-methylpropyl 3-oxopropionate
• 英文别名: isobutyl 4-oxobutanoate；2-methylpropyl 4-oxobutanoate
• CAS: 126101-13-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: AAFMVGHJBLBRHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  216.7±23.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-methylpropyl 3-oxopropionate 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 51.02h， 生成 2'-methylpropyl 3-propionate
  参考文献：
  名称：

  Synthesis of Oxadiazolidinedione Derivatives as Quisqualic Acid Analogs and Their Evaluation at a Quisqualate-Sensitized Site in the Rat Hippocampus

  摘要：

  The ability of quisqualic acid (1) to sensitize neurons to depolarization by omega-phosphono alpha-amino acid analogues of excitatory amino acids is a highly specific phenomenon and is termed the QUIS. effect. In an attempt to elucidate the structure-activity relationships for this sensitization, analogues 2-6 of quisqualic acid have been synthesized. Compounds 4, 5, and 6 showed no quisqualate sensitization with respect to L-2-amino-6-phosphonohexanoic acid (L-AP6), while compounds 2 and 3 were 1/10 and 1/1000, respectively, as active as quisqualic acid in sensitizing neurons toward L-AP6.

  DOI：

  10.1021/jm00049a013
• 作为产物：
  描述：

  异丁基2-环氧乙烷基乙酸酯 在 palladium on activated charcoal 氢气 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 2'-methylpropyl 3-oxopropionate
  参考文献：
  名称：

  Synthesis and pharmacological activity of a series of dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, a novel class of potent cognition enhancers

  摘要：

  A series of dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones were synthesized. These bicylic derivatives contain both the 2-pyrrolidinone and 4-imidazolidinone nuclei, already recognized as important for cognition enhancing activity. In addition, these structures maintain the backbone of piracetam and oxiracetam with the acetamide side chain restricted in a folded conformation. Their ability to reverse scopolamine-induced amnesia was assessed in a one trial, step-through, passive avoidance paradigm. The main features observed are a potent antiamnestic activity after ip administration (minimal effective dose being between 0.3 and 1 mg/kg ip for most compounds), the presence of a bell-shaped dose-response curve and, generally, a reduction of biological activity after po administration. However, the unsubstituted compound (15, dimiracetam) shows no evidence of a bell-shaped dose-response curve and completely retains activity when given orally, being 10-30 times more potent than the reference drug oxiracetam.

  DOI：

  10.1021/jm00078a011

文献信息

• New Tetraphosphorus Ligands for Highly Linear Selective Hydroformylation of Allyl and Vinyl Derivatives
  作者：Chaoxian Cai、Shichao Yu、Bonan Cao、Xumu Zhang

  DOI：10.1002/chem.201201396

  日期：2012.8.6

  New tetraphosphorus ligands have been developed and applied in the rhodium‐catalyzed regioselective hydroformylation of a variety of functionalized allyl and vinyl derivatives. Remarkably high linear selectivity was obtained by these tetraphosphorus ligands. The ligand that bears strong electron‐withdrawing 2,4‐difluorophenyl groups is the most effective one in affording linear aldehydes. The Rh/tetraphosphorus

  已开发出新的四磷配体，并将其用于铑催化的多种功能化的烯丙基和乙烯基衍生物的区域选择性加氢甲酰化反应。这些四磷配体获得了显着高的线性选择性。带有强吸电子的2,4-二氟苯基的配体是提供线性醛最有效的配体。Rh /四磷配体催化剂非常有效地从官能化的烯丙基衍生物生产线性醛，所述烯丙基衍生物具有直接邻近于烯丙基的杂原子或芳族基团。对于乙烯基衍生物，该配体对丙烯酸衍生物，苯乙烯，乙烯基吡啶和乙烯基邻苯二甲酰亚胺具有高度线性的选择性。对于苯乙烯和烯丙基氰化物的加氢甲酰化，分别获得26：1和10：1的线性与支链比。
• Condensed imidazole derivatives, process and intermediates for their preparation and pharmaceutical compositions containing them.
  申请人：ISF SOCIETA PER AZIONI

  公开号：EP0335483A3

  公开（公告）日：1991-12-18

  Compounds of structure (I) in which, R¹ is hydrogen, C₁₋₄alkyl, CHR⁶CONHR⁷ or CHR⁶COOR⁷ in which R⁶ and R⁷ are each hydrogen or C₁₋₄alkyl; R² is hydrogen, C₁₋₅alkyl or a residue R² of an amino acid R² CH(NH₂)COOH; R³ is hydrogen, C₁₋₄alkyl, CONH₂ or CO₂R⁸ in which R⁸ is hydrogen or C₁₋₄alkyl; and n is 2, 3 or 4, processes for their preparation, intermediates useful in their preparation, pharmaceutical composition containing them and their use in therapy as nootropic agents.

  结构式（I）的化合物中，其中R¹为氢，C₁₋₄烷基，CHR⁶CONHR⁷或CHR⁶COOR⁷，其中R⁶和R⁷均为氢或C₁₋₄烷基；R²为氢，C₁₋₅烷基或氨基酸R² CH（NH₂）COOH的残基R²；R³为氢，C₁₋₄烷基，CONH₂或CO₂R⁸，其中R⁸为氢或C₁₋₄烷基；n为2、3或4，其制备方法，用于其制备的中间体，包含它们的制药组合物以及它们作为神经营养剂在治疗中的用途。
• Psychotropic perhydroazacycloalka [1,2-A] imidazole derivatives
  申请人：I.S.F. Societa per Azioni

  公开号：US05053422A1

  公开（公告）日：1991-10-01

  Imidazole derivatives are described which are useful in restoring learning and treating memory difficulties. A compound of the invention is 2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole.

  描述了一种恢复学习能力和治疗记忆困难的咪唑衍生物。该发明的化合物是2,5-二氧代六氢-1H-吡咯[1,2-a]咪唑。
• [EN] PROCESS FOR THE PREPARATION OF DIMIRACETAM<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DIMIRACETAM
  申请人：NEUROTUNE AG

  公开号：WO2012013640A1

  公开（公告）日：2012-02-02

  The invention relates to a method of manufacture of dimiracetam (2,5-dioxohexahydro-1 H-pyrrolo[1,2-a]imidazole), characterized in that a 4-oxo-butanoic acid ester is condensed with glycinamide in a one-pot reaction with a controlled pH. The reaction may be performed in aqueous solution or in an anhydrous lower alcohol solution.

  本发明涉及一种制备二甲酰胺(2,5-二氧己烷基-1H-吡咯[1,2-a]咪唑)的方法，其特征在于将4-氧代丁酸酯与甘氨酰胺在控制pH的单锅反应中缩合。该反应可在水溶液中或无水低级醇溶液中进行。
• Selective hydroformylation of alkyl acrylates using [2,2′-bis(dipyrrolylphosphinooxy)-1,1′-(±)-binaphthyl]/Rh catalyst: reversal of regioselectivity
  作者：Xiao Shu、Haoran Liang、Qianhui Wu、Fanding Zhou、Xueli Zheng、Haiyan Fu、Bin Xu、Ruixiang Li、Chunchun Zhang、Hua Chen

  DOI：10.1039/c7ra01649b

  日期：——

  catalyst could give good conversion of ethyl acrylate (82.9%) in 12 h and exclusive branched aldehyde selectivity of >99.0%. More importantly, on elevating the temperature to 90 °C, this Rh system could preferentially afford the linear aldehyde with 96.1% regioselectivity, and the TOF could reach up to 9000 h−1. Deuterioformylation was conducted to explore the mechanism of regioselectivity reversal, and

  本文研究了铑催化的具有不同PN N二膦配体的丙烯酸烷基酯的加氢甲酰化。在温和的条件下（合成气压力：2 MPa，20°C），2,2'-双（二吡咯基膦酰氧基）-1,1'-（±）-联萘基（L1）铑催化剂可产生良好的丙烯酸乙酯转化率（82.9％ ）在12小时内，专有的支链醛选择性> 99.0％。更重要的是，在将温度升至90°C时，该Rh系统可以优先提供具有96.1％区域选择性的线性醛，并且TOF可以达到9000 h -1。进行了氘代甲酰化以研究区域选择性逆转的机理，结果表明，可逆的氢化铑加成形成Rh-烷基物种可能在这种逆转中起重要作用。在升高的温度下，支链Rh-烷基物质的β-氢化物消除相对强于线性的Rh-烷基，这可能是因为L1由于其庞大而刚性的联萘骨架而在高温下可导致在分支的Rh-烷基物质中相对较大的空间排斥特征。继而，促进了线性Rh-烷基物质向线性醛的发展。