(Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone | 38879-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone
• 英文别名: (Z)-4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5(4H)-one；(4Z)-4-[(3,4-dimethoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one
• CAS: 38879-47-9
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: ABAKBSGPUNJZIZ-POHAHGRESA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethanol (64-17-5))
• 沸点：
  374.3±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  36.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone 在 盐酸 、 乙酰氯 作用下， 生成 Methyl 3-(3,4-dimethoxyphenyl)-2-hydroxyprop-2-enoate
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 反应 8.0h， 以65%的产率得到(Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone
  参考文献：
  名称：

  A Modified Synthesis of (±)-β-Aryllactic acids

  摘要：

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。

  DOI：

  10.1055/s-1992-26228

文献信息

• Optically Pure (<i>S</i>)-6,7-Dimethoxy-1,2,3,4-Tetrahydro-3-Isoquinolinecarboxylic Acid and Asymmetric Hydrogenation Studies Related to Its Preparation
  作者：N. J. O'Reilly、W. S. Derwin、H. C. Lin

  DOI：10.1055/s-1990-26936

  日期：——

  (S)-6,7-Dimethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid has been prepared in optically pure form as its hydrochloride. Pictet-Spengler ring closure of the optically pure (S)-2-amino-3-(3,4-dimethoxyphenyl)propanoic acid hydrochloride salt (L-3,4-dimethoxyphenylalanine hydrochloride) proceeded without significant racemization. A simple and safe, asymmetric hydrogenation catalyst system has been developed which allows the rapid screening of various chiral phosphine ligands via an in situ ionic complex. A protocol was demonstrated which uses a statistical approach to consider the effects of changes in solvent, nitrogen substituent, oxygen substituent, and ligand in the asymmetric hydrogenation of alkyl or aryl (Z)-2-acylamino-3-(3,4-dimethoxyphenyl)-2-propenoate derivatives. This method was used to successfully determine the optimal substrate and conditions for the preparation of enantiomerically pure (S)-2-amino-3-(3, 4-dimethoxyphenyl)propanoic acid hydrochloride salt.

  (S)-6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸已以其氢氯酸盐的形式以光学纯态制备。光学纯的(S)-2-氨基-3-(3,4-二甲氧基苯基)丙酸氢氯酸盐（L-3,4-二甲氧基苯丙氨酸氢氯酸盐）通过Pictet-Spengler环闭合反应进行，未发生显著的消旋化。开发了一种简单且安全的非对称氢化催化体系，该体系允许通过原位离子配合物快速筛选各种手性膦配体。展示了一种采用统计方法的方案，考虑了溶剂、氮取代基、氧取代基和配体变化对烷基或芳基(Z)-2-酰氨基-3-(3,4-二甲氧基苯基)-2-丙烯酸酯衍生物非对称氢化反应的影响。该方法成功确定了制备光学纯(S)-2-氨基-3-(3,4-二甲氧基苯基)丙酸氢氯酸盐的最佳底物和条件。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140023603A1

  公开（公告）日：2014-01-23

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医疗用途，该化合物具有美白皮肤的活性，可抑制酪氨酸酶，因此适用于用于美白皮肤的药物组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药物组合物或保健食品。
• A Facile Preparation of 4-Arylidene-4,5-dihydrooxazol-5-ones using Zeolite as a Cyclodehydrating Agent
  作者：Anima Boruah、Partha P. Baruah、Jagir S. Sandhu

  DOI：10.1039/a802863j

  日期：——

  An efficient new method for the azlactonisation of acylamino acids using zeolite under mild conditions is described; the method is fairly general as well as providing high yields.

  报道了一种在温和条件下使用分子筛对酰胺氨基酸进行高效新方法，该方法具有较高的产率。
• Use of azalactones in a “Pictet-Spengler-like” reaction. Stereoselective synthesis of 1,3,4-substituted tetrahydro-β-carbolines
  作者：Jesús Ezquerra、Carlos Lamas、Alfredo Pastor、Pilar Alvarez、Juan José Vaquero、Will G Prowse

  DOI：10.1016/0040-4039(96)01233-6

  日期：1996.8

  A “Pictet-Spengler-like” reaction between azalactones 1 and conformationally constrained tryptamines 4 in refluxing 1N HCl over 72 h. gave the corresponding tetrahydro-β-carbolines 3 in moderate to good yields. The observed equatorial orientation of the C-1 substituent in the THBC's results from a combination of the thermal reaction conditions and conformational constraints imposed by the starting

  在回流1N HCl的过程中，氮杂内酯1与构象受约束的色胺4之间发生“ Pictet-Spengler样”反应，历时72 h。以中等至良好的产率得到相应的四氢-β-咔啉3。在THBC中观察到的C-1取代基的赤道取向是由热反应条件和起始色胺所施加的构象限制共同导致的。
• Stereoselective synthesis of 1,3,4-substituted tetrahydro-β-carbolines from indoles based on selective transformations
  作者：Jesús Ezquerra、Concepción Pedregal、Carlos Lamas、Alfredo Pastor、Pilar Alvarez、Juan José Vaquero

  DOI：10.1016/s0040-4020(97)00489-4

  日期：1997.6

  nucleophilic aziridine ring opening with a lower order indolyl magnesium cuprate obtaining the α,β-substituted tryptamines 5 and secondly, a “Pictet-Spengler-like” reaction between azalactones 12 and tryptamines 5. Under the acidic reaction conditions used, the thermodynamically favoured tetrahydro β-carbolines 4 are obtained due to the conformational restrictions imposed by the tryptamine substituents

  通过两次选择性转化，从吲哚6中制备了1，3，4-取代的四氢β-咔啉4：首先，用低级吲哚基镁铜酸盐进行亲核氮丙啶开环，得到α，β-取代的色胺5，其次，“氮杂内酯12和色胺5之间的“ Pictet-Spengler样”反应。在所用的酸性反应条件下，由于色胺的取代基所施加的构象限制，获得了热力学上优选的四氢β-咔啉4。