4-[3-(4-tert-Butyl-phenyl)-oxiranyl]-benzoic acid methyl ester | 119436-66-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4-[3-(4-tert-Butyl-phenyl)-oxiranyl]-benzoic acid methyl ester
• 英文别名: Methyl 4-(3-(4-(tert-butyl)phenyl)oxiran-2-yl)benzoate
• CAS: 119436-66-7
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: HOGAKXKCVRJJSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[3-(4-tert-Butyl-phenyl)-oxiranyl]-benzoic acid methyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-[3-(4-tert-Butyl-phenyl)-oxiranyl]-benzoic acid
  参考文献：
  名称：

  Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids

  摘要：

  Alkyl-substituted azobenzene-4-carboxylic acids are potent differentiation inducers of human promyelocytic leukemia cell line HL-60 to mature granulocytes. Their structure-activity relationships are very similar to those of other retinoidal benzoic acids which are generally represented by 4 and named retinobenzoic acids. The structure-activity relationships of azobenzenecarboxylic acids can also be applied to the known retinoid TTNPB (3). Thus, (E)-4-[2-(3,4-diisopropylphenyl)-1-propenyl]benzoic acid (St30 (28] and (E)-4-[2-(3-tert-butylphenyl)ethenyl]benzoic acid (St40 (29], the acyclic alkyl analogues of TTNPB, are nearly as active as retinoic acid. Among the oxidatively derived compounds (Az90, Ep series and Ox series) of azobenzene- or stilbenecarboxylic acids, Az90 (71) and Ep80 (61) have strong activities. However, all the bishydroxylated derivatives of TTNPB are inactive, while a diketo analogue Ox580 (69) has only weak potency. The activities of conformationally restricted compounds of TTNPB offer some information on the stereochemistry of the active form of these retinoidal compounds.

  DOI：

  10.1021/jm00125a027
• 作为产物：
  描述：

  4-叔丁基苄溴 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 苯 为溶剂， 反应 7.0h， 生成 4-[3-(4-tert-Butyl-phenyl)-oxiranyl]-benzoic acid methyl ester
  参考文献：
  名称：

  Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids

  摘要：

  Alkyl-substituted azobenzene-4-carboxylic acids are potent differentiation inducers of human promyelocytic leukemia cell line HL-60 to mature granulocytes. Their structure-activity relationships are very similar to those of other retinoidal benzoic acids which are generally represented by 4 and named retinobenzoic acids. The structure-activity relationships of azobenzenecarboxylic acids can also be applied to the known retinoid TTNPB (3). Thus, (E)-4-[2-(3,4-diisopropylphenyl)-1-propenyl]benzoic acid (St30 (28] and (E)-4-[2-(3-tert-butylphenyl)ethenyl]benzoic acid (St40 (29], the acyclic alkyl analogues of TTNPB, are nearly as active as retinoic acid. Among the oxidatively derived compounds (Az90, Ep series and Ox series) of azobenzene- or stilbenecarboxylic acids, Az90 (71) and Ep80 (61) have strong activities. However, all the bishydroxylated derivatives of TTNPB are inactive, while a diketo analogue Ox580 (69) has only weak potency. The activities of conformationally restricted compounds of TTNPB offer some information on the stereochemistry of the active form of these retinoidal compounds.

  DOI：

  10.1021/jm00125a027

文献信息

• 一种由醇直接合成环氧化合物的方法
  申请人：河北科技大学

  公开号：CN110283146B

  公开（公告）日：2022-09-13

  本发明公开了一种由醇直接合成环氧化合物的方法，该方法以醇为原料，经Swern氧化合成醛，向醛中直接加入溴代烃和碱构建环氧官能团，从而生成环氧化合物，本发明合成路线是：本发明通过采用“一锅法”反应实现了醇的直接环氧化，合成路线简单，制备过程易于控制，过程无需使用催化剂，底物适用范围广泛，反应试剂廉价易得，制备条件温和，反应收率高。本发明适用于合成环氧化合物。