4-p-Anisoyl-3.3-dimethylbuttersaeure | 31526-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-p-Anisoyl-3.3-dimethylbuttersaeure
• 英文别名: 5-(4-Methoxyphenyl)-3,3-dimethyl-5-oxopentanoic acid
• CAS: 31526-44-0
• 化学式: C₁₄H₁₈O₄
• mdl: MFCD17145537
• 分子量: 250.295
• InChiKey: ZLNJJIBOWYMMOG-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C(Solv: benzene (71-43-2))
• 沸点：
  430.8±25.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-p-Anisoyl-3.3-dimethylbuttersaeure 在 吡啶 、 甲基磺酰氯 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists

  摘要：

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.

  DOI：

  10.1021/jm00113a014
• 作为产物：
  描述：

  3,3-二甲基戊二酸酐 、 苯甲醚 在 aluminum (III) chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以80%的产率得到4-p-Anisoyl-3.3-dimethylbuttersaeure
  参考文献：
  名称：

  失活的烯烃酸的对映选择性溴化

  摘要：

  已经开发出使用双官能氨基脲催化剂的α，β-不饱和酮的新型对映选择性溴化。该反应的范围由具有各种官能度的卤代内酯的23个实例证明，产率高达99％，er为99：1 er。与需要缺乏电子的取代基来增强氢键强度的典型尿素催化剂不同，有趣的是，在这种情况下，富含电子的脲对于高对映选择性是必不可少的。此外，实验数据表明，卤代内酯化合物对LPS诱导的RAW 264.7细胞具有相当大的抗炎作用。

  DOI：

  10.1021/acs.orglett.8b01125

文献信息

• Photo-oxidation of aryldihydropyrans
  作者：R. S. Atkinson

  DOI：10.1039/j39710000784

  日期：——

  6-p-Methoxyphenyl-3,4-dihydro-2H-pyran (III) and its 4,4-dimethyl analogue (IV) have been prepared and photo-oxidised. The mechanism of formation of the products, 4-p-anisoyloxybutyraldehyde (XVII) and 4-p-anisoyloxy-2,2-dimethybutyraldehyde (XVIII), is considered.

  制备了 6-对甲氧基苯基-3,4-二氢-2H-吡喃（III）及其 4,4-二甲基类似物（IV），并对其进行了光氧化。研究了生成物 4-对甲氧基丁醛 (XVII) 和 4-对甲氧基-2,2-二甲基丁醛 (XVIII) 的形成机理。
• MATHUR, K. C.;SINGH, V. P., PROC. NAT. ACAD. SCI., INDIA, 1981, 51, N 2, 177-180
  作者：MATHUR, K. C.、SINGH, V. P.

  DOI：——

  日期：——
• GAUTAM, R. K.;KANNAN, S.;SAHARIA, G. S., J. INST. CHEM. (INDIA), 1984, 56, N 2, 71-75
  作者：GAUTAM, R. K.、KANNAN, S.、SAHARIA, G. S.

  DOI：——

  日期：——
• (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists
  作者：Robert D. Dillard、Richard A. Hahn、Doris McCullough、F. Patrick Carr、Lynn E. Rinkema、Carlos R. Roman、Jerome H. Fleisch

  DOI：10.1021/jm00113a014

  日期：1991.9

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.
• Enantioselective Bromolactonization of Deactivated Olefinic Acids
  作者：Xiaojian Jiang、Shenghui Liu、Si Yang、Mei Jing、Lipeng Xu、Pei Yu、Yuqiang Wang、Ying-Yeung Yeung

  DOI：10.1021/acs.orglett.8b01125

  日期：2018.6.1

  A novel enantioselective bromolactonization of α,β-unsaturated ketones using bifunctional amino-urea catalysts has been developed. The scope of the reaction is evidenced by 23 examples of halolactones bearing various functionalities with up to 99% yield and 99:1 er. Unlike typical urea catalysts that require electron-deficient substituents to enhance the hydrogen bond strength, it is interesting to

  已经开发出使用双官能氨基脲催化剂的α，β-不饱和酮的新型对映选择性溴化。该反应的范围由具有各种官能度的卤代内酯的23个实例证明，产率高达99％，er为99：1 er。与需要缺乏电子的取代基来增强氢键强度的典型尿素催化剂不同，有趣的是，在这种情况下，富含电子的脲对于高对映选择性是必不可少的。此外，实验数据表明，卤代内酯化合物对LPS诱导的RAW 264.7细胞具有相当大的抗炎作用。