Methyl 4-(5,6,7,8-tetrahydro-1-hydroxy-5,5,8,8-tetramethylbenzindan-2-yl)benzoate | 119435-93-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: Methyl 4-(5,6,7,8-tetrahydro-1-hydroxy-5,5,8,8-tetramethylbenzindan-2-yl)benzoate
• CAS: 119435-93-7
• 化学式: C₂₅H₃₀O₃
• 分子量: 378.511
• InChiKey: FZWFMFBWZLVINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Methyl 4-(5,6,7,8-tetrahydro-1-hydroxy-5,5,8,8-tetramethylbenzindan-2-yl)benzoate 在 吡啶 、 甲基磺酰氯 作用下， 反应 1.0h， 以42.8%的产率得到Methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzinden-2-yl)benzoate
  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：

  1,1,4,4,6-五甲基-1,2,3,4-四氢化萘 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 氯化亚砜 、 偶氮二异丁腈 、 N,N-二甲基甲酰胺 、 lithium diisopropyl amide 作用下， 以 乙醇 、 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 5.75h， 生成 Methyl 4-(5,6,7,8-tetrahydro-1-hydroxy-5,5,8,8-tetramethylbenzindan-2-yl)benzoate
  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