diethyl 2-(1-phenylbutyl)malonate | 59771-20-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-(1-phenylbutyl)malonate
• 英文别名: (1-phenyl-butyl)-malonic acid diethyl ester；(1-Phenyl-butyl)-malonsaeure-diaethylester；Diethyl 2-(1-phenylbutyl)propanedioate；diethyl 2-(1-phenylbutyl)propanedioate
• CAS: 59771-20-9
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: GCLCOBFIWLFZMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(1-phenylbutyl)malonate 在 氢氧化钾 、 氯化亚砜 、 水 作用下， 以 乙醇 为溶剂， 反应 5.83h， 生成 3-phenyl-hexanoyl chloride
  参考文献：
  名称：

  Maguire, Anita R.; Buckley, N. Rachael; O'Leary, Patrick, Journal of the Chemical Society. Perkin transactions I, 1998, # 24, p. 4077 - 4091

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯基-1-丁醇 在 吡啶 、 sodium ethanolate 、 三溴化磷 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 diethyl 2-(1-phenylbutyl)malonate
  参考文献：
  名称：

  Synthesis and fibrinolytic activity of β-arylaliphatic acids. Quantitative relationships between structure and biological activity

  摘要：

  DOI：

  10.1135/cccc19760633

文献信息

• Novel malonic acid derivatives and process for the manufacture thereof
  申请人：HOFFMANN LA ROCHE

  公开号：US02701804A1

  公开（公告）日：1955-02-08

  The invention comprises coumarin derivatives of the general formula where R1 is an alkyl radical of not more than three carbon atoms and the manufacture of these derivatives by condensing an alkali metal derivative of an aralkyl malonic ester of the formula where R2 represents an alkyl group of not more than three carbon atoms with an acetyl-salicylic halide (preferably the chloride) to give a product of the formula treating this with an alkali-metal alcoholate at a low temperature to give a compound of the formula and hydrolysing and decarboxylating, e.g. by heating with an alkali metal alcoholate or a dilute mineral acid to give the desired 4-hydroxy - coumarin. Alternatively the a - aralkyl-a -(acetylsalicyloyl) malonic ester produced in the first condensation step may be converted directly to the desired 4-hydroxycoumarin without isolation of the intermediate products by heating in an organic solvent with an acidic or basic agent such as an alkali metal alcoholate, e.g. sodium methylate or a dilute acid, e.g. sulphuric acid. In examples: (1) the sodium derivative of diethyl (11-phenylethyl) malonate is treated with acetylsalicylic acid chloride to give 1-(21-acetoxybenzoyl)-1-(11-phenylethyl) malonic acid diethyl ester which is heated with dilute sulphuric acid in ethanol to give 3-(11-phenylethyl)-4-hydroxy-coumarin; (2) diethyl (11-phenylpropyl)-malonate sodium derivative and acetyl salicylic acid chloride are reacted as in (1) to give diethyl 1-(21-acetoxybenzoyl - 1 - (11 - phenylpropyl) - malonate which is treated with sodium methylate to give 3 - carbethoxy - 3 - (11 - phenylpropyl) - 4 - ketodihydrocoumarin which is hydrolysed and decarboxylated by heating with aqueous sodium hydroxide to give 3 - (11 - phenylpropyl) - 4 - hydroxy-coumarin; and (3) a -phenyl-butyl bromide is reacted with diethyl malonate to give diethyl (11-phenylbutyl-malonate) which is converted to its sodium derivative and reacted with acetyl-salicylic acid chloride as in (1) to give diethyl 1-(21-acetoxybenzoyl)-1-(11-phenylbutyl)-malonate which is treated with sodium methylate to give 2-(11-phenylbutyl)-4-hydroxycoumarin.

  这项发明涉及通式为的香豆素衍生物，其中R1是不超过三个碳原子的烷基基团，并通过将通式为的芳基丙二酸酯的碱金属衍生物（其中R2代表不超过三个碳原子的烷基基团）与乙酰水杨酰卤（最好是氯化物）缩合而制备这些衍生物，得到通式为的产物，将其与低温下的碱金属醇酸盐处理得到通式为的化合物，然后水解和脱羧，例如通过与碱金属醇酸盐或稀释的矿酸加热以得到所需的4-羟基香豆素。或者，第一步缩合中产生的a-芳基-a-(乙酰水杨酰)丙二酸酯可以直接转化为所需的4-羟基香豆素，无需通过在有机溶剂中与酸性或碱性剂（如碱金属醇酸盐，如甲基醇钠或稀硫酸）加热而分离中间产物。在示例中：（1）二乙基(11-苯乙基)丙二酸钠衍生物与乙酰水杨酸氯化物反应，得到1-(21-乙酰氧基苯甲酰)-1-(11-苯乙基)丙二酸二乙酯，经过乙醇中稀硫酸加热得到3-(11-苯乙基)-4-羟基香豆素；（2）二乙基(11-苯基丙基)-丙二酸钠衍生物与乙酰水杨酸氯化物如同（1）中反应，得到二乙酯1-(21-乙酰氧基苯甲酰)-1-(11-苯基丙基)-丙二酸，经过甲醇钠处理得到3-羧乙氧基-3-(11-苯基丙基)-4-酮二氢香豆素，通过与水杨酸钠加热水解和脱羧得到3-(11-苯基丙基)-4-羟基香豆素；（3）a-苯基丁基溴化物与二乙基丙二酸反应，得到二乙酯(11-苯基丁基-丙二酸)转化为其钠衍生物，与乙酰水杨酸氯化物如同（1）中反应，得到二乙酯1-(21-乙酰氧基苯甲酰)-1-(11-苯基丁基)-丙二酸，经过甲醇钠处理得到2-(11-苯基丁基)-4-羟基香豆素。
• 10.1021/jacs.4c02682
  作者：Wincenciuk, Aleksandra、Cmoch, Piotr、Giedyk, Maciej、Andersson, Martin P.、Gryko, Dorota

  DOI：10.1021/jacs.4c02682

  日期：——

  years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve the regio-, stereo-, and chemoselectivity of different transformations. Herein, we demonstrate that the aqueous environment is a suitable medium for a visible light driven cobalt-catalyzed reaction involving radical species. In this system

  近年来，依赖水作为反应介质的方法引起了相当多的关注。胶束溶液的独特性质被证明可以提高不同转化的区域选择性、立体选择性和化学选择性。在此，我们证明水环境是涉及自由基物质的可见光驱动的钴催化反应的合适介质。在该系统中，还原的维生素 B 12与卤代烷反应，产生自由基，该自由基被 Stern 层中存在的亲脂性烯烃捕获。一系列核磁共振测量和理论研究揭示了胶束系统中反应组分的位置。
• Synthesis and fibrinolytic activity of β-arylaliphatic acids. Quantitative relationships between structure and biological activity
  作者：M. Kuchař、B. Brůnová、V. Rejholec、Z. Roubal、O. Němeček

  DOI：10.1135/cccc19760633

  日期：——
• Holm, Torkil, Acta Chemica Scandinavica, 1991, vol. 45, # 9, p. 925 - 929
  作者：Holm, Torkil

  DOI：——

  日期：——
• Patra; Kumar Misra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 1, p. 66 - 69
  作者：Patra、Kumar Misra

  DOI：——

  日期：——