ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-methyl-2-butenoate | 169126-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-methyl-2-butenoate
• 英文别名: Ethyl 3-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-2-enoate
• CAS: 169126-65-2
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: OJGCEXJSSBYHNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-methyl-2-butenoate 在 吡啶 、 chromium(VI) oxide 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 6.08h， 生成 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-methyl-2-butenal
  参考文献：
  名称：

  Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity

  摘要：

  The natural retinoid 9-cis-retinoic acid is an activating ligand for both the retinoic acid receptors (RARs) and the retinoid X receptors (RXRs), which are members of the retinoid/thyroid hormone/steroid hormone family of nuclear receptor proteins that activate gene transcription through specific response elements. The pharmacophoric groups necessary to confer RXR selectivity were established by evaluating the ability of 21 conformationally restricted retinoids to activate, the TREpal retinoic acid receptor response element for gene transcription in the presence of one of the three RAR subtypes or RXR alpha. In contrast to those retinoids selective for the RARs, these RXR-selective retinoids have one less atom in the bridge linking the hydrophobic and carboxylic acid termini of the retinoid skeleton. Therefore, a one-carbon bridge replaces the 19-methyl group and SE-double bond of S-cis-retinoic acid and is further functionalized by inclusion in an isopropylidene group, a dioxolane ring, or a cyclopropane ring for optimal RXR alpha activity and selectivity. In addition, the beta-geranylidene and 20-methyl-(11E,13E)-dienoic acid groups of g-cis-retinoic acid are replaced by a 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2 naphthalenyl ring and a 4-carboxylphenyl ring, respectively, for optimal activation and selectivity. RXR alpha; selectivity is reduced on replacement of the 4-carboxylphenyl group by a 2-carboxyl-5-thienyl group or the S-cis-retinoic acid methylpentadienoic acid terminus.

  DOI：

  10.1021/jm00017a021
• 作为产物：
  描述：

  2-溴-3-甲基-2-丁酸乙酯 、 (5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 生成 ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-methyl-2-butenoate
  参考文献：
  名称：

  Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity

  摘要：

  The natural retinoid 9-cis-retinoic acid is an activating ligand for both the retinoic acid receptors (RARs) and the retinoid X receptors (RXRs), which are members of the retinoid/thyroid hormone/steroid hormone family of nuclear receptor proteins that activate gene transcription through specific response elements. The pharmacophoric groups necessary to confer RXR selectivity were established by evaluating the ability of 21 conformationally restricted retinoids to activate, the TREpal retinoic acid receptor response element for gene transcription in the presence of one of the three RAR subtypes or RXR alpha. In contrast to those retinoids selective for the RARs, these RXR-selective retinoids have one less atom in the bridge linking the hydrophobic and carboxylic acid termini of the retinoid skeleton. Therefore, a one-carbon bridge replaces the 19-methyl group and SE-double bond of S-cis-retinoic acid and is further functionalized by inclusion in an isopropylidene group, a dioxolane ring, or a cyclopropane ring for optimal RXR alpha activity and selectivity. In addition, the beta-geranylidene and 20-methyl-(11E,13E)-dienoic acid groups of g-cis-retinoic acid are replaced by a 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2 naphthalenyl ring and a 4-carboxylphenyl ring, respectively, for optimal activation and selectivity. RXR alpha; selectivity is reduced on replacement of the 4-carboxylphenyl group by a 2-carboxyl-5-thienyl group or the S-cis-retinoic acid methylpentadienoic acid terminus.

  DOI：

  10.1021/jm00017a021

文献信息

• α-Arylsulfonyloxyacrylates: attractive <i>O</i>-centered electrophiles for synthesis of α-substituted acrylates <i>via</i> Pd-catalysed Suzuki reactions
  作者：Zhongya Zhang、Li Zhang、Linge Huai、Zhentao Wang、Yewen Fang

  DOI：10.1039/d3ra00401e

  日期：——

  We herein report α-arylsulfonyloxyacrylates as a kind of useful and attractive O-centered electrophiles for Suzuki cross-coupling reactions. A range of α-(hetero)aryl substituted acrylates has been prepared via the palladium-catalysed C–C cross-coupling reactions between potassium (hetero)aryltrifluoroborates and α-arylsulfonyloxyacrylates. Moreover, α-arylsulfonyloxyacrylate could also react with

  我们在此报道了 α-芳基磺酰氧基丙烯酸酯作为一种有用且有吸引力的以 O为中心的亲电子试剂，用于 Suzuki 交叉偶联反应。通过钯催化的（杂）芳基三氟硼酸钾和 α-芳基磺酰氧基丙烯酸酯之间的钯催化 C-C 交叉偶联反应制备了一系列 α-（杂）芳基取代的丙烯酸酯。此外，α-芳基磺酰氧基丙烯酸酯还可以与B-alkyl-9-BBN反应生成α-烷基取代的丙烯酸酯。通过合成维甲酸X受体-选择性维甲酸的中间体的制备证明了这种新方法的合成应用。这些基于 Suzuki 反应的方案具有广泛的底物范围、通用性和温和的反应条件。
• Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity
  作者：Marcia I. Dawson、Ling Jong、Peter D. Hobbs、James F. Cameron、Wan-ru Chao、Michaela Pfahl、Mi-Ock Lee、Braham Shroot、Magnus Pfahl

  DOI：10.1021/jm00017a021

  日期：1995.8

  The natural retinoid 9-cis-retinoic acid is an activating ligand for both the retinoic acid receptors (RARs) and the retinoid X receptors (RXRs), which are members of the retinoid/thyroid hormone/steroid hormone family of nuclear receptor proteins that activate gene transcription through specific response elements. The pharmacophoric groups necessary to confer RXR selectivity were established by evaluating the ability of 21 conformationally restricted retinoids to activate, the TREpal retinoic acid receptor response element for gene transcription in the presence of one of the three RAR subtypes or RXR alpha. In contrast to those retinoids selective for the RARs, these RXR-selective retinoids have one less atom in the bridge linking the hydrophobic and carboxylic acid termini of the retinoid skeleton. Therefore, a one-carbon bridge replaces the 19-methyl group and SE-double bond of S-cis-retinoic acid and is further functionalized by inclusion in an isopropylidene group, a dioxolane ring, or a cyclopropane ring for optimal RXR alpha activity and selectivity. In addition, the beta-geranylidene and 20-methyl-(11E,13E)-dienoic acid groups of g-cis-retinoic acid are replaced by a 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2 naphthalenyl ring and a 4-carboxylphenyl ring, respectively, for optimal activation and selectivity. RXR alpha; selectivity is reduced on replacement of the 4-carboxylphenyl group by a 2-carboxyl-5-thienyl group or the S-cis-retinoic acid methylpentadienoic acid terminus.