Methyl (E)-2-methyl-4-phenyl-4-oxobutenoate | 15732-77-1

• 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: Methyl (E)-2-methyl-4-phenyl-4-oxobutenoate
• 英文别名: methyl (E)-2-methyl-4-oxo-4-phenylbut-2-enoate；α-Methyl-β-benzoyl-acrylsaeuremethylester；trans-2-Methyl-4-oxo-4-phenyl-buten-(2)-saeuremethylester；(E)-2-methyl-4-oxo-4-phenyl-but-2-enoic acid methyl ester；Methyl 2-methyl-4-oxo-4-phenylbut-2-enoate
• CAS: 15732-77-1
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BFZLGHMSECAVAQ-CMDGGOBGSA-N

物化性质

• 沸点：
  304.0±34.0 °C(Predicted)
• 密度：
  1?+-.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：
  0.17
• 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：

  Methyl (E)-2-methyl-4-phenyl-4-oxobutenoate 在 lithium hydroxide monohydrate 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到(E)-2-methyl-3-benzoylpropenoic acid
  参考文献：
  名称：

  (E)-2-Substituted-4-oxo-2-alkenoic Acids 的双不对称氢化：手性 α，γ-二取代 γ-丁内酯的有效合成

  摘要：

  利用Rh/JosiPhos催化体系对( E )-2-甲基-4-氧代-2-链烯酸进行双不对称氢化，获得了光学纯的α，γ-二取代γ-丁内酯，并取得了优异的效果。

  DOI：

  10.1002/ejoc.202200673
• 作为产物：
  描述：

  衣康酸酐 在 三氯化铝 、 硫酸 、 三乙胺 作用下， 生成 Methyl (E)-2-methyl-4-phenyl-4-oxobutenoate
  参考文献：
  名称：

  El-Ghandour,N. et al., Bulletin de la Societe Chimique de France, 1972, p. 2817 - 2829

  摘要：

  DOI：

文献信息

• HIGHLY ENANTIOSELECTIVE ACCESS TO CYCLIC BETA-AMINO ACIDS
  申请人：Nanyang Technological University

  公开号：US20210171436A1

  公开（公告）日：2021-06-10

  Disclosed herein is a method of forming a compound of formula I: wherein the substituents are defined in the specification. In particular, the compounds of formula I can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities.

  本文揭示了一种形成化合物I的方法：其中取代基在规范中定义。特别是，化合物I可以转化为具有卓越光学纯度的带季碳立体中心的氨基酸。
• Highly Chemo- and Enantioselective Hydrogenation of 2-Substituted-4-oxo-2-alkenoic Acids
  作者：Xian Liu、Jialin Wen、Lin Yao、Huifang Nie、Ru Jiang、Weiping Chen、Xumu Zhang

  DOI：10.1021/acs.orglett.0c01618

  日期：2020.6.19

  The highly chemo- and enantioselective hydrogenation of (E)-2-substituted-4-oxo-2-alkenoic acids was established for the first time using the Rh/JosiPhos complex, affording a series of chiral α-substituted-γ-keto acids with excellent results (up to 99% yield and >99% ee) and high efficiency (up to 3000 TON). In addition, the importance of this methodology was further demonstrated by a concise and gram-scale

  （R）/ JosiPhos配合物首次建立了（E）-2-取代-4-氧代-2-氧烯酸的高度化学和对映选择性加氢反应，提供了一系列手性α-取代-γ-酮酸具有出色的结果（高达99％的收率和> 99％的ee）和高效率（高达3000 TON）。另外，该方法的重要性通过抗炎药（R）-氟哌芬的简洁和克级合成得到了进一步证明。
• [EN] CASPASE INHIBITOR COMPRISING 2-ALKYL-4-OXOBUTANOYL GROUP AND PHARMACEUTICAL COMPOSITION THEREOF<br/>[FR] INHIBITEUR DES CASPASES COMPRENANT UN GROUPE 2-ALKYL-4-OXOBUTANOYLE ET COMPOSITION PHARMACEUTIQUE CONTENANT CELUI-CI
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2005035497A1

  公开（公告）日：2005-04-21

  The present invention relates to a compound of the formula (1), pharmaceutically acceptable salt, physiologically hydrolysable ester, hydrate, solvate, or steroisomer thereof having inhibitory activity against caspases. The compound contains unknown new 2-alkyl-4-oxobutanoyl group. Further, the present invention relates to a process for preparing the compound of formula 1 and a method for determining its binding ability for caspases. The compound of formula 1 can be used effectively for the treatment or relief of various diseases caused by caspases.

  本发明涉及一种具有对caspases具有抑制活性的化合物的公式（1），其包括药用可接受的盐、生理可水解的酯、水合物、溶剂合物或其立体异构体。该化合物含有未知的新2-烷基-4-羰基丁酰基团。此外，本发明涉及一种制备公式1化合物的方法以及确定其与caspases结合能力的方法。公式1化合物可有效用于治疗或缓解由caspases引起的各种疾病。
• Acrylic adhesive compositions containing ketonyl (meth)acrylate
  申请人：——

  公开号：US20030032736A1

  公开（公告）日：2003-02-13

  Use of a ketonyl [meth]acrylate as a replacement for at least a substantial portion of the content of hydroxy (lower alkyl) methacrylate in a curable acrylic adhesive composition. Suitably the ketonyl [meth]acrylate is of the formula: 1 wherein: R 1 is H or C 1 -C 5 alkyl, particularly C 1 -C 2 alkyl;R 2 is C 1 -C 5 alkyl, cyclohexyl, phenyl, benzyl, or substituted derivatives of any of the foregoing; and n is 1-5, for example acetonyl methacrylate.

  使用酮基[甲基]丙烯酸酯替代可固化丙烯酸粘合剂组合物中至少大部分羟基（低级烷基）甲基丙烯酸酯的含量。 合适的酮基甲基丙烯酸酯的结构式为 1 其中R 1 是 H 或 C 1 -C 5 烷基，特别是 C 1 -C 2 烷基；R 2 是 C 1 -C 5 烷基、环己基、苯基、苄基或上述任一物质的取代衍生物；n 为 1-5，例如甲基丙烯酸丙酮酯。
• Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids
  作者：Pedro Bonete、Carmen Najera

  DOI：10.1021/jo00090a043

  日期：1994.6

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

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