2-methyl-4-oxo-4-(p-tolyl)butanoic acid | 51037-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-4-oxo-4-(p-tolyl)butanoic acid
• 英文别名: 2-methyl-4-oxo-4-p-tolyl-butyric acid；2-Methyl-4-oxo-4-p-tolyl-buttersaeure；α-Methyl-β-p-toluyl-propionsaeure；1-Oxo-1-p-tolyl-butan-carbonsaeure-(3)；β-p-Toluyl-isobuttersaeure；3-(4-methylbenzoyl)-2-methyl propionic acid；3-(4-Methylbenzoyl)-2-methyl-propionic acid；2-methyl-4-(4-methylphenyl)-4-oxobutanoic acid
• CAS: 51037-04-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: UEOKILRKFFJCLT-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  380.8±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-oxo-4-(p-tolyl)butanoic acid 在 乙醚 、 硫酸 作用下， 生成 2-methyl-4-p-tolyl-pent-3-enoic acid
  参考文献：
  名称：

  Dev, Journal of the Indian Chemical Society, 1948, vol. 25, p. 69,80

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基丁二酸 在 三氯化铝 、 乙酰氯 作用下， 生成 2-methyl-4-oxo-4-(p-tolyl)butanoic acid
  参考文献：
  名称：

  Mayer; Stamm, Chemische Berichte, 1923, vol. 56, p. 1431

  摘要：

  DOI：

文献信息

• Pd(<scp>ii</scp>)/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids
  作者：Xuexin Zhang、Yang Gao、Ronibala Devi Laishram、Kangkui Li、Yong Yang、Yong Zhan、Yang Luo、Baomin Fan

  DOI：10.1039/c9ob00005d

  日期：——

  An efficient Pd/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids is described. This methodology offers a divergent synthesis of α-methyl-γ-keto carboxylic acids, α-methylcarboxylic acids, and lactones starting from α-methylene-γ-keto carboxylic acids via selective hydrogenation by varying the catalytic conditions avoiding the use of high pressure of hydrogen. The

  描述了一种有效的Pd / Zn共催化的α-亚甲基-γ-酮基羧酸的化学选择性加氢反应。该方法学通过改变催化条件避免选择性使用加氢条件，从而通过选择性加氢从α-亚甲基-γ-酮基羧酸开始，提供了α-甲基-γ-酮基羧酸，α-甲基羧酸和内酯的多样化合成方法。氢。该反应还显示出宽的底物耐受性，以良好至优异的产率得到所需产物。
• Coating compositions
  申请人：Ciba-Geigy Corporation

  公开号：US05277709A1

  公开（公告）日：1994-01-11

  A coating composition comprising a) an organic film-forming binder; and b) a corrosion-inhibiting amount of a substantially water-insoluble mono- or poly-basic salt of: i) a ketoacid having the formula I: ##STR1## in which m and n, independently, are 0 or an integer from 1 to 10 provided that the sum of m and n is at least 1; A is C.sub.1 -C.sub.15 alkyl, C.sub.2 -C.sub.15 alkenyl, optionally substituted C.sub.3 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.15 alkyl interrupted by one or more O-, N- or S-atoms, optionally substituted C.sub.6 -C.sub.10 aryl, optionally substituted C.sub.7 -C.sub.12 aralkyl, optionally substituted C.sub.7 -C.sub.12 aralkenyl, a heterocyclic residue or a ferrocenyl residue; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and each is a substituent A, hydrogen, OH, O-C.sub.1 -C.sub.15 alkyl, NH.sub.2, NH(C.sub.1 -C.sub.15 alkyl), N(C.sub.1 -C.sub.15 alkyl).sub.2, CO.sub.2 H, CO.sub.2 (C.sub.1 -C.sub.15 alkyl), SO.sub.3 H, P(O) (OH).sub.2 P(O)(OH)(O-C.sub.1 -C.sub.15 alkyl), P(O) (O-C.sub.1 -C.sub.15 alkyl).sub.2, SH, S(C.sub.1 -C.sub.15 alkyl), nitro, cyano, halogen or two of R.sub.1, R.sub.2 R.sub.3 and R.sub.4, together with the carbon atoms to which they are attached, form a C.sub.3 -C.sub.12 cycloalkyl ring or C.sub.6 - or C.sub.10 aryl ring, or one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 together with the carbon atom to which it is attached, and with the group A--C(.dbd.O)--, forms a ring, or R.sub.1 and R.sub.2, R.sub.3 and R.sub.4 form a carbonyl group or a C.dbd.C double bond, provided that A is not optionally substituted C.sub.6 -C.sub.10 aryl when R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are simultaneously hydrogen and provided that R.sub.1 and R.sub.2, or R.sub.3 and R.sub.4, respectively, are not simultaneously both OH or both NH.sub.2 ; and ii) a base selected from a) a cation of Group Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, VIa, VIIa or VIIIa of the Periodic Table of Elements; b) an amine of formula II which is specified herein.

  一种涂层组合物，包括a)有机成膜粘合剂；和b)具有防腐作用的、基本上不溶于水的单基或多基盐，所述盐为：i)具有式I的酮酸的防腐量，其中m和n分别为0或1到10的整数，但m和n的和至少为1；A为C.sub.1-C.sub.15烷基、C.sub.2-C.sub.15烯基、可选取代的C.sub.3-C.sub.12环烷基、由一个或多个O、N或S原子中断的C.sub.2-C.sub.15烷基、可选取代的C.sub.6-C.sub.10芳基、可选取代的C.sub.7-C.sub.12芳基烷基、可选取代的C.sub.7-C.sub.12芳基烯基、杂环残基或二茂铁残基；R.sub.1、R.sub.2、R.sub.3和R.sub.4相同或不同，每个都是取代基A、氢、OH、O-C.sub.1-C.sub.15烷基、NH.sub.2、NH(C.sub.1-C.sub.15烷基)、N(C.sub.1-C.sub.15烷基).sub.2、CO.sub.2H、CO.sub.2(C.sub.1-C.sub.15烷基)、SO.sub.3H、P(O)(OH).sub.2P(O)(OH)(O-C.sub.1-C.sub.15烷基)、P(O)(O-C.sub.1-C.sub.15烷基).sub.2、SH、S(C.sub.1-C.sub.15烷基)、硝基、氰基、卤素或R.sub.1、R.sub.2、R.sub.3和R.sub.4中的两个，连同它们附着的碳原子，形成C.sub.3-C.sub.12环烷基环或C.sub.6-或C.sub.10芳基环，或者R.sub.1、R.sub.2、R.sub.3和R.sub.4中的一个与它所附着的碳原子以及A-C(.dbd.O)--基团一起形成一个环，或者R.sub.1和R.sub.2、R.sub.3和R.sub.4分别形成一个羰基或C.dbd.C双键，但当R.sub.1、R.sub.2、R.sub.3和R.sub.4同时为氢时，A不是可选取代的C.sub.6-C.sub.10芳基，且当R.sub.1和R.sub.2或R.sub.3和R.sub.4同时为OH或NH.sub.2时，它们不同时存在；和ii)从元素周期表的Ia、Ib、IIa、IIb、IIIa、IIIb、IVa、IVb、Va、VIa、VIIa或VIIIa组的阳离子中选择的碱或式II所指定的胺。
• Catalytic Enantioselective α-Allylation of Deconjugated Butenolides with Aza-π-allylpalladium 1,4-Dipoles: Access to Optically Pure 2-Piperidones Bearing an All-Carbon Quaternary Stereocenter
  作者：Shu-Pei Yuan、Qing Bao、Ting-Jia Sun、Jian-Qiang Zhao、Zhen-Hua Wang、Yong You、Yan-Ping Zhang、Ming-Qiang Zhou、Wei-Cheng Yuan

  DOI：10.1021/acs.orglett.2c03383

  日期：2022.11.18

  4-diploes, in situ generated from palladium-mediated decarboxylation of cyclic carbamates and amide-substituted acyclic carbonates, has been successfully developed. An array of enantioenriched 2-piperidones bearing an all-carbon quaternary stereocenter were obtained in high yields with excellent enantioselectivities (up to 99% yield and 99% ee). The utility of this method was also showcased by a large-scale

  已成功开发钯催化的去共轭丁烯酸内酯与氮杂-π-烯丙基钯 1,4-二倍体的对映选择性 α-烯丙基化反应，该反应由钯介导的环状氨基甲酸酯和酰胺取代的无环碳酸酯的脱羧原位生成。以高产率和出色的对映选择性（高达 99% 产率和 99% ee）获得了一系列带有全碳季立构中心的对映体富集 2-哌啶酮。该方法的实用性也通过产品的大规模反应和合成转化得到展示。
• Magnesium-Promoted Reductive Carboxylation of Aryl Vinyl Ketones: Synthesis of γ-Keto Carboxylic Acids
  作者：Suhua Zheng、Tianyuan Zhang、Hirofumi Maekawa

  DOI：10.1021/acs.joc.2c00557

  日期：2022.6.3

  Direct reductive carboxylation of easily prepared aryl vinyl ketones under the atmosphere of carbon dioxide led to the selective formation of γ-keto carboxylic acids in 38–86% yields. The reaction is characterized by the carbon–carbon bond formation of carbon dioxide at the β-position of enone, with the use of magnesium turnings that can be easily handled as the reducing agent and the eco-friendly

  容易制备的芳基乙烯基酮在二氧化碳气氛下的直接还原羧化导致以 38-86% 的产率选择性形成 γ-酮基羧酸。该反应的特点是二氧化碳在烯酮的β位形成碳-碳键，使用易于处理的镁屑作为还原剂，以及无加压、无压力等环保反应条件。反应温度低或高，反应时间短。该协议显示了广泛的底物范围，并提供了一种有用且方便的替代方法来获取生物学上重要的 γ-酮羧酸。
• Nuhn, Peter; Radman; Hermann, Pharmazie, 1998, vol. 53, # 12, p. 825 - 829
  作者：Nuhn, Peter、Radman、Hermann、Marx

  DOI：——

  日期：——