Ethyl (E)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylate | 119436-57-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Ethyl (E)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylate
• 英文别名: Ethyl 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylate；ethyl (E)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-2-enoate
• CAS: 119436-57-6
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: DJIVMDONQGHKQD-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl (E)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylate 在 palladium on activated charcoal sodium hydroxide 、 三氯化铝 、 氯化亚砜 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 5,5,8,8-tetramethyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one
  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：

  6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘 在 正丁基锂 、 叔丁基锂 作用下， 反应 7.0h， 生成 Ethyl (E)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylate
  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

• Bi-aromatic compounds, compositions containing them and uses
  申请人：Centre International de Recherches Dermatologiques

  公开号：US06326510B1

  公开（公告）日：2001-12-04

  The invention relates to novel biaromatic compounds having general formula I and their use in pharmaceutical compositions for use in human and veterinary medicine, in particular for treating dermatological, rheumatic, respiratory, cardiovascular, and ophthalmological disorders, and for use in cosmetic compositions.

  该发明涉及具有一般式I的新型双芳香化合物及其在人类和兽医药物组合物中的应用，特别用于治疗皮肤病、风湿病、呼吸系统疾病、心血管疾病和眼科疾病，并用于化妆品组合物中。
• US6326510B1
  申请人：——

  公开号：US6326510B1

  公开（公告）日：2001-12-04
• Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids
  作者：Hiroyuki Kagechika、Toshiyuki Himi、Koushi Namikawa、Emiko Kawachi、Yuichi Hashimoto、Koichi Shudo

  DOI：10.1021/jm00125a027

  日期：1989.5

  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.