(2E)-3-methyl-4-oxo-4-phenylbut-2-enoic acid | 35504-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E)-3-methyl-4-oxo-4-phenylbut-2-enoic acid
• 英文别名: 3-methyl-4-oxo-4-phenyl-trans-crotonic acid；3-methyl-4-oxo-4-phenyl-crotonic acid；3-Methyl-4-oxo-4-phenyl-trans-crotonsaeure；3-Oxo-2-methyl-3-phenyl-propen-(1)-carbonsaeure-(1)；γ-Oxo-β-methyl-γ-phenyl-α-propylen-α-carbonsaeure；β-Methyl-β-benzoyl-acrylsaeure；3-Methyl-4-oxo-4-phenyl-crotonsaeure；β-Benzoyl-crotonsaeure；(E)-3-methyl-4-oxo-4-phenylbut-2-enoic acid
• CAS: 35504-92-8
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: HNHGQBDWKKMPCN-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (2E)-3-methyl-4-oxo-4-phenylbut-2-enoic acid 生成 (2Z)-3-methyl-4-oxo-4-phenylbut-2-enoic acid
  参考文献：
  名称：

  The cis- and trans-β-Aroyl-α- and β-methylacrylic Acids and β-Aroyl-α-methylenepropionic Acids

  摘要：

  DOI：

  10.1021/ja01116a045
• 作为产物：
  描述：

  苯 、 Methyl 4-chloro-3-methyl-4-oxobut-2-enoate 在 三氯化铝 作用下， 生成 (2E)-3-methyl-4-oxo-4-phenylbut-2-enoic acid
  参考文献：
  名称：

  The cis- and trans-β-Aroyl-α- and β-methylacrylic Acids and β-Aroyl-α-methylenepropionic Acids

  摘要：

  DOI：

  10.1021/ja01116a045

文献信息

• CIAT with simultaneous epimerization at two stereocenters. Synthesis of substituted β-methyl-α-homophenylalanines
  作者：Dušan Berkeš、Pavol Jakubec、Dagmar Winklerová、František Považanec、Adam Daich

  DOI：10.1039/b613103d

  日期：——

  Diastereoselective aza-Michael additions of phenylethylamine to 3-aroylbutenoic acids are reported. During these processes, efficient control over two new stereogenic centers on the Michael acceptor has been possible via crystallization-induced asymmetric transformation (CIAT). As an application, a convenient two-step synthesis of anti-beta-methylhomophenylalanines is also described.

  报道了苯乙胺向3-芳基丁烯酸的非对映选择性氮杂-迈克尔加成。在这些过程中，可以通过结晶诱导的不对称转化（CIAT）有效控制迈克尔受体上的两个新的立体异构中心。作为一种应用，还描述了一种方便的两步合成抗β-甲基高苯丙氨酸的方法。
• 7-Substituted bicyclic pyrazolidinones
  申请人：ELI LILLY AND COMPANY

  公开号：EP0202046A1

  公开（公告）日：1986-11-20

  7-Substituted bicyclic pyrazolidinone compounds as antimicrobials and the corresponding intermediates, are discussed or provided. The use of the antimicrobial compounds in pharmaceutical compositions and in methods for treating bacterial infections is set forth. The pyrazolidinone compounds are of the formula wherein one of R1 and R2 is hydrogen, halo, C1 to C6 alkyl, C1 to C6 substituted alkyl, perfluoro C2 to C4 alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl, a heterocyclic ring, nitro or cyano; a group of the formula wherein X is fluoro, chloro, bromo or iodo; a group of the formula wherein z is 0, 1 or 2 and R7 is C1 to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl or a heterocyclic ring; a group of the formula wherein R8 is hydrogen, C1 to C6 alkyl, C, to C6 substituted alkyl, perfluoro C2 to C4 alkyl, trihalomethyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl, amino, (monosubstituted)amino, or (disubstituted)amino; a group of the formula wherein R9 is hydrogen, an organic or inorganic cation, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl, a carboxy-protecting group, or a non-toxic, metabolically-labile, ester-forming group; a group of the formula wherein R10 is hydrogen, an organic or inorganic cation, C1 to C5 alkyl, C, to G6 aubatituted allcyl, C7 to C12 arylalkyl, C7 to C12 aubatltuted arylalkyl, phenyl, or substituted phenyl; a group of the formula ⊕ wherein -N≡Q is a quaternary ammonium group; or a group of the formula -CH2-S-Heterocycllc ring; a group of the formula wherein R11 is hydrogen, C1 to Ce alkyl, C, to Ce substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl or C1 to C7 acyl; or a group of the formula wherein R12 and R13 are the same or different and are hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl, C1 to C7 acyl, or a group of the formula; wherein Rq is C, to C6 alkyl, C7 to C12 arylalkyl or phenyl; and the other of R, and R2 is a group of the formula wherein R14 is hydrogen, an organic or inorganic cation, a carboxy-protecting group or a non-toxic, metabolically-labile ester-forming group; and R3 and R4 are the same or different and are hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl or a group of the formula wherein R15 has the same definition as R9; R5 and R6 are: 1) each hydrogen, an amino protecting group; or acyl group derived from a C, to C30 carboxylic acid; provided that at least one of Rs and R6 must be hydrogen; or 2) taken together to form a phthalimido group; or a pharmaceutically-acceptable salt thereof.

  讨论或提供了作为抗菌剂的 7-取代双环吡唑烷酮化合物及相应的中间体。阐述了抗菌化合物在药物组合物和治疗细菌感染方法中的用途。吡唑烷酮化合物的结构式如下 其中 R1 和 R2 之一为氢、卤素、C1 至 C6 烷基、C1 至 C6 取代烷基、全氟 C2 至 C4 烷基、C7 至 C12 芳烷基、C7 至 C12 取代芳烷基、苯基、取代苯基、杂环、硝基或氰基； 式中的基团 其中 X 是氟、氯、溴或碘； 式中的基团 其中 z 是 0、1 或 2，R7 是 C1 至 C6 烷基、C1 至 C6 取代的烷基、苯基、取代的苯基、C7 至 C12 芳烷基、C7 至 C12 取代的芳烷基或杂环； 式中的基团 其中 R8 是氢、C1 至 C6 烷基、C, 至 C6 取代的烷基、全氟 C2 至 C4 烷基、三卤甲基、C7 至 C12 芳烷基、C7 至 C12 取代的芳烷基、苯基、取代的苯基、氨基、(单取代)氨基或(二取代)氨基； 式中的基团 其中 R9 是氢、有机或无机阳离子、C1～C6 烷基、C1～C6 取代的烷基、C7～C12 芳烷基、C7～C12 取代的芳烷基、苯基、取代的苯基、羧基保护基团或无毒、代谢上易腐烂的酯形成基团； 式中的基团 其中 R10 是氢、有机或无机阳离子、C1 至 C5 烷基、C, 至 G6 亚氨基全烷基、C7 至 C12 芳烷基、C7 至 C12 亚氨基芳烷基、苯基或取代苯基； 式中的基团 ⊕ 其中-N≡Q 是季铵基团；或式中-CH2-S-杂环的基团； 式中的基团 其中 R11 是氢、C1 至 Ce 烷基、C1 至 Ce 取代的烷基、C7 至 C12 芳烷基、C7 至 C12 取代的芳烷基、苯基、取代的苯基或 C1 至 C7酰基；或式中的基团 其中 R12 和 R13 相同或不同，并且是氢、C1 至 C6 烷基、C1 至 C6 取代的烷基、C7 至 C12 芳烷基、C7 至 C12 取代的芳烷基、苯基、取代的苯基、C1 至 C7酰基或式中的基团； 其中 Rq 是 C 至 C6 烷基、C7 至 C12 芳烷基或苯基；以及 R 和 R2 中的另一个是式中的基团 其中 R14 是氢、有机或无机阳离子、羧基保护基团或无毒、可代谢的成酯基团； R3 和 R4 相同或不同，并且是氢、C1 至 C6 烷基、C1 至 C6 取代的烷基、C7 至 C12 芳烷基、C7 至 C12 取代的芳烷基、苯基、取代的苯基或式中的一个基团。 其中 R15 的定义与 R9 相同； R5 和 R6 为 1) 各为氢、氨基保护基；或由 C 至 C30 羧酸衍生的酰基； 但 Rs 和 R6 中至少有一个必须是氢；或 2) 结合在一起形成邻苯二甲酰亚胺基团；或其药学上可接受的盐。
• Bogert; Ritter, Journal of the American Chemical Society, 1925, vol. 47, p. 532
  作者：Bogert、Ritter

  DOI：——

  日期：——
• Carbonylacrylic derivatives as potential antimicrobial agents. Correlations between activity and reactivity toward cysteine
  作者：Alma Dal Pozzo、Maurizio Acquasaliente、Giovanni Donzelli、Paolo De Maria、M. Christina Nicoli

  DOI：10.1021/jm00392a026

  日期：1987.9

  A number of 3-carbonylacrylic acid derivatives were prepared, with a view to varying systematically the stereoelectronic environment of the conjugated double bond. The rates of reaction with cysteine were measured spectrophotometrically when possible or by stopped flow when very fast. Some of the final reaction products were isolated. Other properties examined were partition substituent constants and antimicrobial activity. On the basis of published data and these studies, the activity appears to be the combined effect of at least two mechanisms, one probably related to the effect of these structures on surface tension, the other to the electrophilic properties of the unsaturated system.
• v. Pechmann, Chemische Berichte, 1882, vol. 15, p. 885
  作者：v. Pechmann

  DOI：——

  日期：——