3-(4-methylphenyl)-2-carboxy-2-propenoic acid | 21405-59-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-methylphenyl)-2-carboxy-2-propenoic acid
• 英文别名: 2-(4-Methylbenzylidene)malonic acid；(4-methyl-benzylidene)-malonic acid；(4-Methyl-benzyliden)-malonsaeure；2-[(4-methylphenyl)methylidene]propanedioic acid
• CAS: 21405-59-4
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: DTESVSJGQRBZEK-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  395.6±30.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)-2-carboxy-2-propenoic acid 以 乙醇 、 水 为溶剂， 反应 24.0h， 以93%的产率得到4-methylcinnamic acid
  参考文献：
  名称：

  A one-pot synthesis of 3-amino-3-arylpropionic acids

  摘要：

  3-Aminopropionic acids (beta-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these beta-amino acids. The reaction mechanism of this one-pot synthesis of beta-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00824-4
• 作为产物：
  描述：

  2-[(4-甲基苯基)亚甲基丙二酸二乙酯 在 氢氧化钾 作用下， 生成 3-(4-methylphenyl)-2-carboxy-2-propenoic acid
  参考文献：
  名称：

  Chrzaszczewska, Roczniki Chemii, vol. 5, p. 61

  摘要：

  DOI：

文献信息

• Hypervalent iodine(III) catalyzed radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes under photolysis
  作者：Sermadurai Selvakumar、Qi-Kai Kang、Natarajan Arumugam、Abdulrahman I. Almansour、Raju Suresh Kumar、Keiji Maruoka

  DOI：10.1016/j.tet.2017.08.018

  日期：2017.10

  bearing (−)-8-phenylmenthol as a chiral auxiliary with aliphatic aldehydes is realized under photolysis. This work represent the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The reaction is initiated by the photolysis of hypervalent iodine(III) catalyst under mild and metal-free conditions. The synthetic potential

  在光解作用下，实现了带有（-）-8-苯基薄荷醇作为手性助剂的亚烷基丙二酸酯的高价碘（III）催化的非对映选择性自由基加氢酰化。这项工作代表了将酰基非对映选择性加成至烯烃，从而以高度立体选择性的方式得到手性酮的第一个例子。该反应是通过在温和且不含金属的条件下光解高价碘（III）催化剂而引发的。该方法的合成潜力已通过（-）-亚甲基乳酸内酯的短时正式合成得到了证明。
• Synthesis, Characterization and Antimicrobial Activity of Novel Pharmacophores Incorporating Imidazoline-Oxazoline Scaffold
  作者：Assem Barakat、Abdullah Mohammed Al-Majid、Faisal M. Al-Qahatany、Mohammad Shahidul Islam、Mohamed H.M. Al-Agamy

  DOI：10.5012/bkcs.2014.35.2.562

  日期：2014.2.20

  In this work, synthesis, characterization and antimicrobial activity of series of imidazolines-oxazolines scaffolds 5a-f and 10a-d have been investigated. All the imidazolines-oxazolines derivatives were prepared from acid derivatives 1 and 6a-c, and enantiomerically pure (S)-2-amino-3-methyl-1-butanol in four steps with excellent optical purity. The structures of all newly synthesized compounds have been elucidated by $^1H$, $^13}C$ NMR, GCMS, and IR spectrometry. Their purity was confirmed using elemental analysis. Some newly synthesized compounds were examined to in-vitro antimicrobial activity. Among the prepared products 10d was found to exhibits the most active against all tested bacteria and fungi with minimal inhibitory concentration (MIC) ranged between 21.9 and $42.6\mu}g/mL$.

  在本研究中，合成、表征及一系列咪唑啉-噁唑啉骨架5a-f和10a-d的抗微生物活性进行了探讨。所有咪唑啉-噁唑啉衍生物均由酸类衍生物1和6a-c以及对映体纯净的(S)-2-氨基-3-甲基-1-丁醇经过四步反应合成，且具有极好的光学纯度。所有新合成化合物的结构通过^1H NMR、^13C NMR、GCMS和IR光谱进行了解释。它们的纯度通过元素分析得到确认。部分新合成的化合物进行了体外抗微生物活性测试。在所制备的产品中，10d被发现对所有测试的细菌和真菌具有最高的活性，最小抑菌浓度（MIC）范围为21.9至42.6 μg/mL。
• New imidazopyridine derivatives as angiotensin II antagonists
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0669333A1

  公开（公告）日：1995-08-30

  The present invention relates to new imidazopyridine derivatives of formula I wherein: one of A, B, C and D is N and the other are CR, wherein each R independently represents hydrogen, C1-4 alkyl, COOH or halogen; R1 represents C1-4 alkyl or C3-7 cycloalkyl; Ar1 represents phenylene or pyridylene which can be optionally substituted; V represents C1-4 alkyl, C3-7 cycloalkyl, aryl, aryl-(C1-4)alkyl or a 5- or 6-membered aromatic heterocycle; the group X-Y represents C = C or CH-CR3; R3 represents hydrogen, C1-4 alkyl or aryl-(C1-4)alkyl; Z represents among others -CO2R4, -tetrazol-5-yl, -CONHS02R4, -CONR4R5, -CH2NHSO2R4; R4 and R5 independently represent hydrogen, C1-4 alkyl, aryl, aryl-(C1-4)alkyl or perfluoro-(C1-4)alkyl; W represents hydrogen, cyano, C1-4 alkyl, C1-4 haloalkyl, C3-7 cycloalkyl, aryl, aryl-(C1-4)alkyl, C1 -4 alkylsulfonyl, C1 -4 alkylsulfinyl, C1 -4 alkylthio, C1 -4 alkoxy, C1-4 alkylcarbonyl, halogen, hydroxymethyl or C1-4 alkoxymethyl, or W can have any of the meanings disclosed for Z. These compounds are angiotensin II antagonists.

  本发明涉及公式I的新咪唑吡啶衍生物，其中：A、B、C和D中的一个为N，另外三个为CR，其中每个R独立地代表氢、C1-4烷基、COOH或卤素；R1代表C1-4烷基或C3-7环烷基；Ar1代表苯基或吡啶基，可以选择性地被取代；V代表C1-4烷基、C3-7环烷基、芳基、芳基-(C1-4)烷基或5-或6-成员芳香杂环；X-Y基团代表C = C或CH-CR3；R3代表氢、C1-4烷基或芳基-(C1-4)烷基；Z代表等等的基团之一，如-CO2R4、-四唑-5-基、-CONHSO2R4、-CONR4R5、-CH2NHSO2R4；R4和R5独立地代表氢、C1-4烷基、芳基、芳基-(C1-4)烷基或全氟-(C1-4)烷基；W代表氢、氰基、C1-4烷基、C1-4卤代烷基、C3-7环烷基、芳基、芳基-(C1-4)烷基、C1-4烷基磺酰基、C1-4烷基亚砜基、C1-4烷基硫基、C1-4烷氧基、C1-4烷基羰基、卤素、羟甲基或C1-4烷氧甲基，或W可以具有Z所披露的任何含义。这些化合物是血管紧张素II拮抗剂。
• Microwave Enhanced Knoevenagel Condensation of Malonic Acid on Basic Alumina
  作者：Pan-Suk Kwon、Young-Mee Kim、Chul-Joong Kang、Tae-Woo Kwon、Sung-Kee Chung、Young-Tae Chang

  DOI：10.1080/00397919708005456

  日期：1997.12

  Abstract: An improved Knoevenagel condensation of malonic acid and aldehydes can be achieved by microwave irradiation over alumina. A number of diacids were prepared in good yields in very short reaction times.

  摘要：通过微波辐射氧化铝可以实现丙二酸和醛的改进的 Knoevenagel 缩合。在很短的反应时间内以良好的收率制备了许多二酸。
• Solvent-free bentonite-catalyzed condensation of malonic acid and aromatic aldehydes under microwave irradiation
  作者：André Loupy、Suk-Jin Song、Sun-Mee Sohn、Young-Mee Lee、Tae-Woo Kwon

  DOI：10.1039/b009803p

  日期：——

  Solvent-free condensation between malonic acid and aromatic aldehydes is studied in the presence of bentonite. Various diacids are prepared in good to moderate yields and in very short reaction times under microwave irradiation.

  研究了在膨润土存在下，丙二酸与芳香醛之间的无溶剂缩合反应。在微波辐射条件下，通过非常短的反应时间制备出了各种二酸，产率从中等到良好不等。